91780-35-7

Upstream product

• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 13265-84-4 D-glucal 
• 2873-29-2 D-glucal triacetate 
• 160549-11-1 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 

Downstream Products

• 74545-15-6 3,4,6-Tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranose 
• 91780-41-5 3,4,6-tri-O-benzyl-1,2-dideoxy-1,5-anhydro-D-arabino-hexitol 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 91780-38-0 (1S)-1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-α-D-(1-2H)arabino-hexitol 
• 91780-38-0 (1R)-1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-D-⁽²⁾H-arabino-hexitol 
• 98933-78-9 phenyl-(3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexapyranosyl)ketone 
• 98933-79-0 1-(3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexapyranosyl)-1-hexanone 
• 121386-95-6 (2R,3S,4R,6R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-6-phenyltetrahydro-2H-pyran 

Relevant academic research and scientific papers

Light-Mediated Cross-Coupling of Anomeric Trifluoroborates

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

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

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

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

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

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

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.

Stereospecific Generation of α- and β-Glycosyl-lithium Reagents from Glycosyl-stannanes: a Stereocontrolled Route to α- and β-C-Glycosides

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.

Preparation and reductive lithiation of 2-deoxy-D-glucopyranosyl phenylsulfones: A highly stereoselective route to C-glycosides

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

Simple Generation of a Reactive Glycosyl-lithium Derivative

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.