CAS: 18546-37-7; (3R,4S)-3,4,5-Trihydroxypentanal

该化合物是一种阴茎糖,是核酸的重要组成部分,特别是在DNA结构中.它是一种焊接开胃糖,意思是含有5个碳原子和一个甲酰二甲酰功能组."2-脱氧"的称谓表明,它与对DNA稳定性和结构至关重要的肋骨相比,在第二个碳中缺乏氧原子.这种糖存在于开放链和循环形式中,循环形式在溶液中占主导地位.2-脱氧-L-肋骨通常存在于乙氧-D-发泡形态中,它有助于DNA双螺旋的整体稳定性.它在水中溶解,具有甜味,与其他糖类似.2-脱氧-L-肋骨的化学配方是C5H10O4,它在细胞代谢和核糖混合物合成中发挥着关键作用,而后者是DNA的构件.它的独特结构和特性使得它成为基因信息储存和生物生物转移的基本条件.

结构式图片

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

CAS号446251-73-6 甲基-2-脱氧-L-赤式戊呋喃糖 | CAS号817621-81-1 methyl 2-deoxy-... | CAS号624-45-3 乙酰丙酸甲酯 | CAS号686-21-5 4,5,5-trimethox... | CAS号123-76-2 乙酰丙酸

合成工艺路线路线简述

  • 合成目标产物 2-Deoxy-L-Ribose 主要起始原料 Sulfuric Acid And D-Erythro-Pent-4-Enitol, 1,5-Anhydro-4-Deoxy-
  • (文献来源)合成步骤主要原料 Sulfuric Acid 和 D-Erythro-Pent-4-Enitol, 1,5-Anhydro-4-Deoxy-
1-T-Butoxy-2-Deoxy-L-Ribose置于甲苯,2-脱氧-L-核糖,L-Anilide体系中,用 溶剂黄146 用作溶剂,化学反应 5.0H,反应生成2-脱氧-L-核糖
参考文献:Preparation Method Of 2-Deoxy-L-Ribose
标题:Preparation Method Of 2-Deoxy-L-Ribose
摘要:本发明公开了一种制备以下式i所示的2-脱氧-L-核糖的方法.该制备方法包括以下步骤:在酸的存在下,用醇溶剂处理l-阿拉伯糖以制备1-烷氧基-L-阿拉伯吡喃糖;让制备好的1-烷氧基-L-阿拉伯吡喃糖与酰氯反应,以制备1-烷氧基-2,3,4-三酰基-L-阿拉伯吡喃糖;溴化制备好的1-烷氧基-2,3,4-三酰基-L-阿拉伯吡喃糖的烷氧基,以制备1-溴基-2,3,4-三酰基化合物;在乙酸乙酯和有机碱的存在下,让制备好的化合物与锌反应,以制备葡萄糖醛;在酸的存在下,用醇溶剂处理葡萄糖醛,以制备1-烷氧基-2-脱氧-3,4-二酰基-L-核糖吡喃糖;用碱处理制备好的1-烷氧基-2-脱氧-3,4-二酰基-L-核糖吡喃糖,以制备1-烷氧基-2-脱氧-L-核糖吡喃糖;在酸催化剂的存在下,水解制备好的1-烷氧基-2-脱氧-L-核糖吡喃糖.

海关参考信息

专利信息


专利号:US-2022395800-A1
优先权日:2019-11-04
标题:Device for automated synthesis of oligo- and polysaccharides
发明人:SEEBERGER PETER H; DANGLAD FLORES JOSE; LE MAI HOANG KIM; PARDO VARGAS ALONSO; SLETTEN ERIC; SALWICZEK MARIO
权利人:MAX PLANCK GESELLSCHAT ZU RFERDERUNG DER WSS E V; GlycoUniverse GmbH & Co KG&A
摘要:The present invention generally relates to automated synthesis technology, and more particularly, to a device and method for automated synthesis of oligo- and polysaccharides on a solid support. In particular the present invention relates to a device for automated synthesis of oligo- and polysaccharides on a solid support comprising a reaction vessel, a reagent storing component, a reagent delivery system, a cooling device for cooling reaction vessel, and a pre-cooling device for pre-cooling the reagents to be supplied.

专利号:WO-9839347-A3
优先权日:1997-03-05
标题:Synthesis of l-ribose and 2-deoxy l-ribose
发明人:JUNG MICHAEL E; XU YUE
权利人:UNIV CALIFORNIA; JUNG MICHAEL E; XU YUE
摘要:A method for synthesizing L-ribose (1) and 2-deoxy L-ribose (12) from inexpensive D-ribose (2) is provided. The 5-O-trityl ribose (3) (prepared in 70 % yield from D-ribose) is reduced with borohydride to give the tetrol (4), which is then peracetylated to the tetraacetate (5). Hydrolysis of the trityl ether followed by Swern oxidation affords the aldehyde (7) via the alcohol (6). This aldehyde is a protected form of L-ribose, being L-ribose 2,3,4,5,-tetraacetate. Mild basic hydrolysis of the acetate affords L-ribose itself (1), thus ending an efficient six-step synthesis of (1) from (2) which proceeds in 39 % overall yield. In a second aspect of the invention, L-ribose is converted into the β-selenophenyl ribofuranoside (10) via the tetraester (9) in 71 % isolated yield for the four steps. Treatment of (10) with tributylstannane and AIBN furnishes in 84 % yield the tribenzoyl 2-deoxy-L-ribofuranoside (11) which, on basic hydrolysis, gives 2-deoxy L-ribose (12) in high yield. In a third aspect of the invention, L-arabinose (13) is converted into 2-deoxy L-ribose (12) via the arabinopyranosyl bromide (14), via similar reductive rearrangement with tributylstannane to give the 2-deoxy ribopyranose tribenzoate (16). Hydrolysis yields 2-deoxy L-ribose. In a third aspect of the invention, L-arabinose is converted into 2-deoxy L-ribose by an alternate route.

专利号:US-7125983-B2
优先权日:2000-11-29
标题:L-nucleic acid derivatives and process for the synthesis thereof
发明人:IIZUKA HAJIME; TOGASHI KAZUHIKO; SUZUKI TSUNEJI
权利人:MITSUI CHEMICALS INC
摘要:A novel method has been found to produce 2,2′-anhydro-1-(β-L-arabinofuranosyl)thymine as a novel useful intermediate compound. A novel method has been further found to produce thymidine from 2,2′-anhydro-1-(β-L-arabinofuranosyl)thymine. A novel method has been further found to L-2′-deoxyribose derivatives as a useful synthetic intermediate through L-2,2′-anhydro-5,6-dihydrocyclouridine derivative. According to these methods, synthesis of various L-nucleic acid derivatives, synthesis of which has been difficult till now.

专利号:US-2022288005-A1
优先权日:2019-07-26
标题:Synthesis of pro-resolving analogs and compositions therefor
发明人:VAN DYKE THOMAS E; SERHAN CHARLES N
权利人:NOCENDRA INC
摘要:This disclosure relates to methods of synthesizing certain lipoxin analogs (e.g., lipoxin mimetics, etc.) and pharmaceutical compositions comprising these pro-resolving compounds. Methods of administering the lipoxin mimetics (e.g., lipoxin A4 mimetics, lipoxin B4 mimetics, etc.) to patients in need thereof are also provided.

专利号:US-7582748-B2
优先权日:2003-03-20
标题:Methods of manufacture of 2′-deoxy-β-L-nucleosides
发明人:RABI JAIME A
权利人:MICROBIOL QUIMICA FARMACEUTICA
摘要:The present invention relates to the synthesis of 2′-deoxy-β-L-thymidine, 2′-deoxy-β-L-uridine and 2′-deoxy-β-L-cytidine, and their derivatives, such as the 3′-O-acyl or 3′,5′-O-diacyl prodrugs, including the 3′-O-L-aminoacyl and 3′,5′-O-L-diaminoacyl prodrugs, and particularly the 3′-O-L-valinyl and 3′,5′-O-L-divalinyl prodrugs.

专利号:US-8431693-B2
优先权日:2004-04-05
标题:Process for desilylation of oligonucleotides
发明人:MANOHARAN MUTHIAH; JUNG MICHAEL F; RAJEEV KALLANTHOTTATHIL G; PANDEY RAJENDRA K; WANG GANG
权利人:MANOHARAN MUTHIAH; JUNG MICHAEL F; RAJEEV KALLANTHOTTATHIL G; PANDEY RAJENDRA K; WANG GANG; ALNYLAM PHARMACEUTICALS INC
摘要:The present invention relates to processes and reagents for oligonucleotide synthesis and purification. One aspect of the present invention relates to compounds useful for activating phosphoramidites in oligonucleotide synthesis. Another aspect of the present invention relates to a method of preparing oligonucleotides via the phosphoramidite method using an activator of the invention. Another aspect of the present invention relates to sulfur-transfer agents. In a preferred embodiment, the sulfur-transfer agent is a 3-amino-1,2,4-dithiazolidine-5-one. Another aspect of the present invention relates to a method of preparing a phosphorothioate by treating a phosphite with a sulfur-transfer reagent of the invention. In a preferred embodiment, the sulfur-transfer agent is a 3-amino-1,2,4-dithiazolidine-5-one. Another aspect of the present invention relates to compounds that scavenge acrylonitrile produced during the deprotection of phosphate groups bearing ethylnitrile protecting groups. In a preferred embodiment, the acrylonitrile scavenger is a polymer-bound thiol. Another aspect of the present invention relates to agents used to oxidize a phosphite to a phosphate. In a preferred embodiment, the oxidizing agent is sodium chlorite, chloroamine, or pyridine-N-oxide. Another aspect of the present invention relates to methods of purifying an oligonucleotide by annealing a first single-stranded oligonucleotide and second single-stranded oligonucleotide to form a double-stranded oligonucleotide; and subjecting the double-stranded oligonucleotide to chromatographic purification. In a preferred embodiment, the chromatographic purification is high-performance liquid chromatography.
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合成参考文献


参考文献:10.1007/s10637-008-9175-7
摘要:Myers T, Chengedza S, Lightfoot S, Pan Y, Dedmond D, Cole L, Tang Y, Benbrook DM. Flexible heteroarotinoid (Flex-Het) SHetA2 inhibits angiogenesis in vitro and in vivo. Investigational New Drugs. 2008 Sep 18;27(4):304–18. doi: 10.1007/s10637-008-9175-7.
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