91780-35-7Relevant academic research and scientific papers
Light-Mediated Cross-Coupling of Anomeric Trifluoroborates
Miller, Eric M.,Walczak, Maciej A.
supporting information, p. 4289 - 4293 (2021/06/28)
Stereoselective reactions at the anomeric carbon constitute the cornerstone of preparative carbohydrate chemistry. Here, we report stereoselective C-arylation and etherification reactions of anomeric trifluoroborates derived from BMIDA esters. These react
Synthesis of glycosyl chlorides using catalytic Appel conditions
Pongener, Imlirenla,Nikitin, Kirill,McGarrigle, Eoghan M.
supporting information, p. 7531 - 7535 (2019/08/20)
The stereoselective synthesis of glycosyl chlorides using catalytic Appel conditions is described. Good yields of α-glycosyl chlorides were obtained using a range of glycosyl hemiacetals, oxalyl chloride and 5 mol% Ph3PO. For 2-deoxysugars treatment of the corresponding hemiacetals with oxalyl chloride without phosphine oxide catalyst also gave good yields of glycosyl chloride. The method is operationaly simple and the 5 mol% phosphine oxide by-product can be removed easily. Alternatively a one-pot, multi-catalyst glycosylation can be carried out to transform the glycosyl hemiacetal directly to a glycoside.
Highly stereoselective glycosyl-chloride-mediated synthesis of 2-deoxyglucosides
Verma, Ved Prakash,Wang, Cheng-Chung
, p. 846 - 851 (2013/02/23)
Cl intermediates: The glycosylation of per-O-benzylated 2-deoxy- and 2,6-dideoxythioglycosides, promoted by the combination of para-toluenesulfenyl chloride (p-TolSCl) and silver triflate (AgOTf), furnished the products in high yields and high stereoselec
Cyclopropenium cation promoted dehydrative glycosylations using 2-deoxy- and 2,6-dideoxy-sugar donors
Nogueira, Jason M.,Nguyen, Son Hong,Bennett, Clay S.
supporting information; experimental part, p. 2814 - 2817 (2011/07/30)
Dehydrative glycosylation reactions using 2-deoxy- and 2,6-dideoxy-sugar donors promoted by a combination of 3,3-dichloro-1,2-diphenylcyclopropene and tetrabutylammonium iodide (TBAI) are described. The reactions are α-selective and proceed under mild con
Synthesis of 2-deoxy-α- and -β-D-arabino-hexopyranosyl phosphonic acids and related compounds; analogues of early intermediates in the shikimate pathway
Barnes, Nigel J.,Probert, Mark A.,Wightman, Richard H.
, p. 431 - 438 (2007/10/03)
Treatment of 1-O-acetyl-3,4,6-tri-O-benzyl-2-deoxy-D-arabino-hexopyranose 18 with trimethyl phosphite in the presence of trimethylsilyl triflate gave a separable mixture of dimethyl (3,4,6-tri-O-benzyl-α-D-arabino-hexopyranosyl)phosphonate 19 (35%) and the β-anomer 20 (60%). The diethyl analogue of compound 20 could be prepared stereoselectively from tributyl (3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranosyl)stannane 21 and diethyl chlorophosphate. Reaction of 1,3,4,6-tetra-O-acetyl-2-deoxy-D-arabino-hexopyranose 23 with trimethyl phosphite and trimethylsilyl triflate gave dimethyl (3,4,6-tri-O-acetyl-2-deoxy-α-D-arabino-hexopyranosyl)phosphonate 25 and the β-anomer 27 with some α-selectivity. Deprotection of compounds 25 and 27 gave the phosphonic acids 11 and 12 respectively. The esters 25 and 27 could be converted into methyl 3,4,6-tri-O-acetyl-2-deoxy-1-(dimethoxyphosphoryl)-β-D-arabino- hexopyranoside 31 by free-radical bromination followed by methanolysis, and diethyl [3,4,6-tri-O-(tert-butyldiphenylsilyl)-2-deoxy-D-arabino-hex-1-enopyranosyl) phosphonate 33 was prepared by interaction of the 1-lithioglucal with diethyl chlorophosphate. Metallation of stannane 21 and reaction with methyl chloroformate gave methyl 2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-gluco-heptonate 35 which could be alkylated with tert-butyl bromoacetate to give, after deprotection, 3,7-anhydro-3-carboxy-2,4-dideoxy-D-gluco-octonic acid 14.
Diastereoselective Free-radical Reactions. Part 1. Preparation of 2-Deoxy-β-glycosides by Synthesis and Reductive Decarboxylation of 3-Deoxyulosonic Acid Glycosides
Crich, David,Ritchie, Timothy J.
, p. 945 - 954 (2007/10/02)
A general procedure for the synthesis of 2-deoxy-β-D-glycosides involving the preparation of 3-deoxyulosonic acid glycosides from glycals and their reductive decarboxylation is described.
STEREOCONTROLLED PREPARATION OF C-2-DEOXY-α- AND -β-D-GLUCOPYRANOSYL COMPOUNDS FROM TRIBUTYL-(2-DEOXY-α- AND -β-D-GLUCOPYRANOSYL)STANNANES
Lesimple, Patrick,Beau, Jean-Marie,Sinay, Pierre
, p. 289 - 300 (2007/10/02)
Tributylstannyllithium treatment of 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranosyl chloride (2) provided selectively tributyl (3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexopyranosyl)stannane (3) in 85percent yield.Isomeric tributyl (3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranosyl)stannane (6) could be prepared in 70percent yield by reductive lithiation of 2 and reaction with tributyltin chloride.Tin-lithium exchange reaction, performed on 3 and 6 with butyllithium in oxolane at -78 deg C, generated the corresponding, configurationally stable 2-deoxy-β- and -α-D-hexopyranosyllithium compounds which reacted with electrophilic compounds with retention of configuration.Addition of these glycosyllithium reagnts to prochiral carbonyl compounds gave variable degrees of facial selectivity.A significant diastereofacial discrimination (10:1) was observed by condensation of 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranosyllithium reagent with hexanal and isobutyraldehyde.The structure of all C-glycopyranosyl compounds obtained was established by 1H-n.m.r. spectroscopy.
Preparation and reductive lithiation of 2-deoxy-D-glucopyranosyl phenylsulfones: A highly stereoselective route to C-glycosides
Beau,Sinay
, p. 6185 - 6188 (2007/10/02)
2-Deoxy-D-glucopyranosyl phenylsulfones 3a-c have been synthesized in 75-83% yield from commercial tri-O-acetyl-D-glucal 1. Their reductive desulfonylation by lithium naphthalenide and reaction of the intermediate glycosyl-lithium 5 with aldehydes leads t
Stereospecific Generation of α- and β-Glycosyl-lithium Reagents from Glycosyl-stannanes: a Stereocontrolled Route to α- and β-C-Glycosides
Lesimple, Patrick,Beau, Jean-Marie,Sinay, Pierre
, p. 894 - 895 (2007/10/02)
Treatment of α- and β-D-tri-n-butylstannyl-glucopyranosides with n-butyl-lithium at -78 deg C generates configurationally stable α- and β-D-glycosyl-lithium species which accept electrophiles with retention of configuration.
Simple Generation of a Reactive Glycosyl-lithium Derivative
Lancelin, Jean-Marc,Morin-Allory, Luc,Sinay, Pierre
, p. 355 - 356 (2007/10/02)
Two-step hydrolithiation of 3,4,6-tri-O-benzyl-D-glucal (hydrochlorination and lithium naphthalenide reductive lithiation) gives a reactive glycosyl-lithium derivative which is shown to be a precursor of C-glycosides.
