CAS: 55628-54-1; 3,4,6-Tri-O-Benzyl-D-Glucal

上下游产品

1,2-didehydrodideoxyallose benzyl bromide 1,5-anhydro-3,6-di-O-acetyl-2-deoxy-D-ribo-hex-1-enitol 3,4,6-tri-O-acetyl-D-glucal (2R,3R,4R,5S,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-phenylsulfanyl-tetrahydro-pyran (2R,3R,4R,5R,6R)-3,4-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-5-phenylsulfanyl-tetrahydro-pyran 3,4,6-tri-O-benzyl-2-C:1-N-carbonyl-2-deoxy-β-D-altro-pyranosylamine 3,4,6-tri-O-benzyl-2,5-anhydro-D-allose dimethylacetal

Phenyl 2-O-Acetyl-3,4,6-Tri-O-Benzyl-1-Thio-α-D-Mannopyranoside置于samarium Diiodide,碳酸氢钠,间氯过氧苯甲酸体系中,用 四氢呋喃,二氯甲烷 作为反应溶剂,化学反应 27.0H,反应生成 3,4,6-三苄氧基-D-葡萄烯糖
参考文献:1,2-Cis-C-Glycoside Synthesis By Samarium Diiodide-Promoted Radical Cyclizations
标题:1,2-Cis-C-Glycoside Synthesis By Samarium Diiodide-Promoted Radical Cyclizations
摘要:Abstractthe Samarium Diiodide Reduction Of Glycosyl Pyridyl Sulfones Bearing A Silicon‐tethered Unsaturated Group At The C2-oh Position Leads To The Stereo‐specific Synthesis Of 1,2‐cis‐c‐glycosides In Good Yield After Desilylation. These Reactions Proceed Via An Anomeric Radical With Subsequent 5‐exo Cyclization. Unlike The Corresponding Glycosyl Phenyl Sulfones,The Pyridyl Derivatives React Instantaneously With Samarium Diiodide And Do Not Require A Cosolvent Such As Hexamethylphosphoramide (Hmpa). Under These Reaction Conditions Radical Cyclization Precedes The Second Reduction Step. Examples Of 5‐exo‐trig And ‐dig Ring Closures Are Given. The Synthetic Utility Of This Method Was Demonstrated By A Short Synthesis Of Methyl C‐isomaltoside.
DOI:10.1002/chem.19970030822

专利信息

专利号:US-7102023-B2
优先权日:1999-11-24
标 题:Protecting groups useful in the synthesis of polysaccharides, natural products, and combinatorial libraries
发明人：BUCHWALD STEPHEN L; PLANTE OBADIAH J; SEEBERGER PETER H
权利人:MASSACHUSETTS INST TECHNOLOGY
摘要:One aspect of the present invention relates to optionally substituted halogenated benzyl halides and the like. These compounds are useful as halogenated benzyl ether-based protecting groups for a variety of functional groups. Another aspect of the present invention relates to use of said protecting groups in an orthogonal protecting group strategy for the synthesis of complex molecules that comprise a number of suitable functional groups. Another aspect of the present invention relates to saccharides bearing various arrays of protecting groups of the present invention. Another aspect of the present invention relates to a method of synthesizing an oligosaccharide or glycoconjugate, comprising the steps of: using a saccharide bearing at least one protecting group of the present invention to glycosylate a second molecule to give a product comprising said saccharide; and removing a protecting group of the present invention from said product.

专利号:US-9834515-B2
优先权日:2014-05-09
标题 :Process for synthesis of piperidine alkaloids
发明人：BHATTACHARYA ASISH KUMAR; CHAND HEMENDER RAMI
权利人:COUNCIL SCIENT IND RES
摘要:The present invention discloses a process for synthesis of piperidine alkaloids selected from fagomine, 4-epi-fagomine and nojirimycin from tri-O-benzyl-D-glucal or tri-O-benzyl-D-galactal.

专利号:US-6933382-B2
优先权日:2002-12-31
标题:Process for the synthesis of 2-deoxy-D-glucose
发明人：MEREYALA HARI BABU; KUMAR MAMIDYALA SREEMAN
权利人:COUNCIL SCIENT IND RES
摘要:The present invention provides a process for the synthesis of 2-deoxy-D-glucose comprising haloalkoxylation of R-D-Glucal wherein R is selected from H and 3, 4, 6-tri-O-benzyl, to obtain alkyl 2-deoxy-2-halo-R-α/β-D-gluco/mannopyranoside, converting alkyl 2-deoxy-2-halo-R-α/β-D-gluco/mannopyranoside by reduction to alkyl 2-deoxy-α/β-D-glucopyranoside, hydrolysing alkyl 2-deoxy-α/β-D-glucopyranoside to 2-deoxy-D-glucose.

专利号:WO-9102739-A1
优先权日:1989-08-11
标题:Synthesis of glycosides having predetermined stereochemistry
发明人：DANISHEFSKY SAMUEL J
权利人:UNIV YALE
摘要:Methods of stereoselectively preparing a substituted 1,2-anhydrosugar wherein a substituted glycal is converted into a 1,2-anhydrosugar that is utilized to glycosylate a hydroxyl group containing glycal, are disclosed. Methods of preparing a saccharide multimer wherein a nucleophile is reacted with a substituted 1,2-anhydrosugar having a plurality of non-participating substituents, are disclosed. In addition, methods of preparing stereospecific halo-substituted saccharide multimers by haloglycosylation of a glycosyl donor substituted glycal and a glycosyl acceptor glycal derivative in the absence of water and in the presence of a halonium ion, are disclosed. Methods of preparing stereospecific particle-linked halo-substituted saccharide multimers, by haloglycosylation of a particle-linked nucleophilic hydroxyl group with a substituted glycal and a halonium ion, are also disclosed.

专利号:US-9181293-B2
优先权日:2009-11-24
标 题 :Method for the synthesis of aspalathin and analogues thereof
发明人：VAN DER WESTHUIZEN JAN HENDRIK; FERREIRA DANEEL; JOUBERT ELIZABETH; BONNET SUSSANA LUCIA
权利人:VAN DER WESTHUIZEN JAN HENDRIK; FERREIRA DANEEL; JOUBERT ELIZABETH; BONNET SUSSANA LUCIA; SOUTH AFRICAN MEDICAL RES COUNCIL
摘要:A method of synthesising Aspalathin and its analogues or derivatives is disclosed. The method comprises synthesising a compound of formula 1 or its analogues or derivatives: n n n n n n n n n n n n wherein n each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 is independently selected from the group consisting of —H, —OH, hydrocarbyl groups, saccharide moieties and —OR 15 ; n R 15 is selected from the group consisting of hydrogen, a hydrocarbyl group (e.g. methoxy or ethoxy), an acyl group and a benzyl group; and n R 11 , R 12 , R 13 and R 14 are independently selected from the group consisting of —H, hydrocarbyl groups, saccharide moieties, an acyl group and a benzyl group. The method comprises the step of coupling a sugar to a dihydrochalcone, chalcone or flavanone, or coupling the sugar to an intermediate for producing a dihydrochalcone, chalcone or flavanone followed by coupling of the sugar-intermediate adduct to a further intermediate for producing a dihydrochalcone, chalcone or flavanone, and transforming the product thereof into a compound of formula 1 or an analogue or derivative thereof.

专利号:US-10774043-B2
优先权日:2016-05-06
标题 :Glycolactam compounds, process for preparation and uses thereof
发明人：BHATTACHARYA ASISH KUMAR; CHAND HEMENDER RAMI
权利人:COUNCIL SCIENT IND RES
摘要:The present invention discloses compounds of Formula I, n nwherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are independently selected from H, OBn, OH, CH 2 OBn, CH 2 OH, CH 3 ; R 9 is selected from alkyl, substituted alkyl, hydroxyl alkyl, alkenyl, benzyl; process for preparation of N-alkylated glycolactam compounds of Formula I and their use for the synthesis of piperidine alkaloids and their analogues.