CAS: 21343-40-8; (S,Z)-3-(2-((1R,3As,7Ar,E)-1-((2R,5S,E)-6-Hydroxy-5,6-Dimethylhept-3-En-2-yl)-7A-Methyloctahydro-4H-Inden-4-Ylidene)Ethylidene)-4-Methylenecyclohexan-1-Ol

该化合物是一种固醇,是一种活性维生素D的代谢物. 它在钙和磷代谢中发挥着至关重要的作用,对维持骨骼健康和整体生理功能至关重要.该化合物在将维生素D3(胆碱酯酶)或维生素D2(ergocalciferol)合成在皮肤或食用中摄入后,从肝脏中产生,即25-Hydroxyvitamin D,通常在血液中测量,以评估一个人的维生素D状况. 25-Hydroxyvitamin D反映了从阳光和饮食来源获得的维生素D总量.该物质的特征是脂肪溶解性,允许将其储存在人体组织中.其生物活动主要通过维生素D受体进行介介介,影响与钙吸收和骨质矿化有关的基因表达.25-氢氧基氧基D的缺陷可导致各种健康问题,包括儿童体内的硬质DD,该物质在213的化合物中识别.

结构式图片

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ECHA物质C&L通报REACH预注册

上下游产品

CAS号100858-20-6 (22R)-des-A,B-8... | CAS号73295-12-2 (2S)-2,3-dimeth... | CAS号93748-49-3 (R)-2,3-dimethy... | CAS号93748-46-0 4-Benzyloxy-2,3... | CAS号93748-50-6 (R)-2,3-二甲基-4-(... | CAS号62748-09-8 [(2R)-3,3-dimet... | CAS号71312-15-7 2,2-dimethyl-3-... | CAS号77517-57-8 (2S)-2-((3S,9S,... | CAS号60133-18-8 1α,25-二羟维生素 D2

合成工艺路线路线简述

    (2S)-2-((3S,9S,10R,13R,14R,17R)-10,13-Dimethyl-3-((Tetrahydro-2H-Pyran-2-yl)Oxy)-2,3,4,9,10,11,12,13,14,15,16,17-Dodecahydro-1H-Cyclopenta[a]Phenanthren-17-yl)Propan-1-Ol置于4-甲基苯磺酸吡啶 Disodium Hydrogenphosphate,Sodium Amalgam,草酰氯,乙醇,三乙胺,Lithium Diisopropyl Amide体系中,用 二甲基亚砜 用作溶剂,化学反应生成25-羟基维生素 D2
    参考文献:25-羟基维生素d 2的简便立体选择合成
    标题:25-羟基维生素d 2的简便立体选择合成
    摘要:25-羟基维生素d 2的合成是首次并通过sharpless的手性环氧化和随后的区域选择性和立体选择性的甲基化与二甲基铜酸锂进行立体选择性合成,从而在c(24)处引入所需的手性,并还原消除了邻位羟基砜以立体选择性地在目标分子的c(22)处引入e双键.
    Doi:10.1016/s0040-4039(01)81381-2

    海关参考信息

    专利信息


    专利号:US-5089647-A
    优先权日:1989-03-09
    标题:Method for preparing intermediates for the synthesis of steroid side chains in optically active form
    发明人:DELUCA HECTOR F; SCHNOES HEINRICH K; PERLMAN KATO L
    权利人:WISCONSIN ALUMNI RES FOUND
    摘要:This invention provides a novel method for the preparation of optically active arylalykylsulfone derivatives, having a chiral center in the alkyl moiety in either the (R)- or the (S)-configuration. These optically active sulfones find use in the stereospecific synthesis of steroid or vitamin D compounds having chiral center at either carbon 24 or carbon 25 of the side chain. The method comprises the steps of reacting an optically active sulfinate ester having a chiral center at sulfur with a racemic alkyl Grignard reagent to obtain a mixture of diastereomeric sulfoxides, separating the mixture of diastereomeric sulfoxides, and oxidizing separately each of the diastereomers to obtain the desired optically active sulfone.

    专利号:WO-2025108575-A1
    优先权日:2023-11-21
    标 题:Methods of selective deprotection and synthesis of transhydrindane- skeleton-based compounds
    发明人:HUBER FLORIAN MAURITIUS ERASMUS
    权利人:ROCHE DIAGNOSTICS GMBH
    摘要:The present invention relates to methods of selectively deprotecting a transhydrindane-skeleton-based compound comprising at least two different silyl ether groups. The present invention further relates to methods of synthesizing a Vitamin D molecule and to Vitamin D molecules obtainable by such processes. Furthermore, the present invention relates to a compound according to formula (I) comprising two different silyl ether groups, its use in the synthesis of Vitamin D molecules and to methods of producing such a compound.

    专利号:US-2024239742-A1
    优先权日:2022-12-29
    标 题 :Synthesis of vitamin d3 from cholesterol extracted from fish oil
    发明人:VALENCIA OCAMPO JHESUA; MARTINEZ GUTIERREZ WILSON DE JESÚS; VALDEZ CANTILLO WENDY KATHERINE
    权利人:VALENCIA OCAMPO JHESUA; MARTINEZ GUTIERREZ WILSON DE JESUS; VALDEZ CANTILLO WENDY KATHERINE
    摘要:The present invention provides synthetic methods and preparation of cholecalciferol (vitamin D3) from cholesterol, which is a by-product of the Omega-3 oil production process. According to the invention, dehydro-cholesterol is prepared and subjected to UV radiation (254 nm). Accordingly, two new synthetic alternatives are provided; wherein the first consists of processes of oxidation-reduction of cholesterol to form dehydro-cholesterol and subsequent UV radiation; which route involves six steps (see scheme 1). The second transformation involves the generation of vitamin D3 by means of a bromination method and a photocatalytic reaction using UV radiation; which alternative requires four steps (see scheme 2).

    专利号:US-9006412-B2
    优先权日:2008-10-06
    标题 :Expression vector for pseudonocardia autotrophica
    发明人:FUJII YOSHIKAZU; FUJII TADASHI; ARISAWA AKIRA; TAMURA TOMOHIRO
    权利人:FUJII YOSHIKAZU; FUJII TADASHI; ARISAWA AKIRA; TAMURA TOMOHIRO; MICROBIOPHARM JAPAN CO LTD; NAT INST OF ADVANCED IND SCIEN
    摘要:An expression vector capable of expressing a foreign gene in Pseudonocardia autotrophica ; a transformant of Pseudonocardia autotrophica produced by using the expression vector; a method for producing a protein by using the transformant; a method for producing an active form of vitamin D3 from vitamin D3, which comprises highly expressing a gene encoding an enzyme involved in the synthesis of the active form of vitamin D3 in a transformant by using the expression vector or the transformant; a method for producing 25-hydroxyvitamin D2 from vitamin D2; and a method for producing pravastatin from compactin, which comprises highly expressing a compactin hydroxylase gene in a transformant by using the expression vector or the transformant.

    专利号:EP-1494680-B1
    优先权日:2002-03-25
    标题 :Use of carbon-2-modified-vitamin d analogs to induce the formation of new bone
    发明人:DELUCA HECTOR F; PIKE J WESLEY; SHEVDE NIRUPAMA K
    权利人:WISCONSIN ALUMNI RES FOUND
    摘要:It has been discovered that the 2-carbon-modified derivatives of 1α,25-dihydroxyvitamin D3 specifically stimulate osteoblasts to form new bone. The ability of the 2-carbon-modified vitamin D analogs to stimulate new bone formation suggest that these compounds can be used where synthesis of new bone is required. Thus, these compounds can be used either systemically or locally to stimulate the growth of bone transplants, to increase the rate of fracture healing and thereby reduce the time required for the healing of fractures, the stimulation of bone growth when required for replacement surgery, and also for the growth of bone to implants or other devices required to maintain the skeleton or teeth in the proper positions.

    专利号:US-5869472-A
    优先权日:1994-07-18
    标 题 :Synthesis of 1α-hydroxy vitamin D
    发明人:MORIARTY ROBERT M; GUO LIANG; PENMASTA RAJU A
    权利人:BONE CARE INT INC
    摘要:A method for 1α-hydroxylation of vitamin D compounds using the appropriate vitamin D as the starting material. The method requires no separatory procedures prior to the actual hydroxylation step.
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    主要参考文献


    1: Skuladottir GV, Cohen A, Arnar DO, Hougaard DM, Torfason B, Palsson R, Indridason OS. Plasma 25-hydroxyvitamin D2 and D3 levels and incidence of postoperative atrial fibrillation. J Nutr Sci. 2016 Feb 15;5:e10. doi: 10.1017/jns.2015.38. eCollection 2016.
    2: Freeman J, Wilson K, Spears R, Shalhoub V, Sibley P. Performance evaluation of four 25-hydroxyvitamin D assays to measure 25-hydroxyvitamin D2. Clin Biochem. 2015 Nov;48(16-17):1097-104. doi: 10.1016/j.clinbiochem.2015.05.021. Epub 2015 Jun 6. doi: 10.1186/s12933-015-0231-2.
    4: Kwak HS, Chung HJ, Cho DH, Park MH, Ku ES, Park EJ, Oh HJ. Efficacy of the measurement of 25-hydroxyvitamin D2 and D3 levels by using PerkinElmer liquid chromatography-tandem mass spectrometry vitamin D kit compared with DiaSorin radioimmunoassay kit and Elecsys vitamin D total assay. Ann Lab Med. 2015 Mar;35(2):263-5. doi: 10.3343/alm.2015.35.2.263. Epub 2015 Feb 12.

    合成参考文献


    参考文献:10.1016/j.cca.2011.05.010
    摘要:Schleicher RL, Encisco SE, Chaudhary-Webb M, Paliakov E, McCoy LF, Pfeiffer CM. Isotope dilution ultra performance liquid chromatography-tandem mass spectrometry method for simultaneous measurement of 25-hydroxyvitamin D2, 25-hydroxyvitamin D3 and 3-epi-25-hydroxyvitamin D3 in human serum. Clin Chim Acta. 2011 Aug 17;412(17-18):1594–9. doi: 10.1016/j.cca.2011.05.010.
    参考文献:10.3945/jn.112.169144
    摘要:El Hayek J, Pham TT, Finch S, Hazell TJ, Jean-Philippe S, Vanstone CA, Agellon S, Rodd C, Rauch F, Weiler HA. Vitamin D Status in Montréal Preschoolers Is Satisfactory Despite Low Vitamin D Intake. The Journal of Nutrition. 2013 Feb;143(2):154–60. doi: 10.3945/jn.112.169144.
    参考文献:10.3945/jn.112.167858
    摘要:Gallo S, Phan A, Vanstone CA, Rodd C, Weiler HA. The Change in Plasma 25-Hydroxyvitamin D Did Not Differ between Breast-Fed Infants That Received a Daily Supplement of Ergocalciferol or Cholecalciferol for 3 Months. The Journal of Nutrition. 2013 Feb;143(2):148–53. doi: 10.3945/jn.112.167858.
    参考文献:10.1016/j.cca.2012.12.018
    摘要:Su Z, Slay BR, Carr R, Zhu Y. The recognition of 25-hydroxyvitamin D2 and D3 by a new binding protein based 25-hydroxyvitamin D assay. Clin Chim Acta. 2013 Feb 18;417():62–6. doi: 10.1016/j.cca.2012.12.018.
    摘要:Xia S, Xia X, Wang W, Yu L, Jin J, Lin X, Ding R, Li S, Jiang Y. [Associations of ulcerative colitis with vitamin D receptor gene polymorphisms and serum levels of 25-hydroxyl vitamin D]. Zhonghua Yi Xue Za Zhi. 2014 Apr 15;94(14):1060–6.
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