73445-31-5

Upstream product

• 20672-66-6 3,4,5-tri-O-benzyl-D-galactopyranose 
• 98-88-4 benzoyl chloride 
• 6597-18-8 (dibenzoyloxyiodo)benzene 
• 80040-79-5 3,4,6-tri-O-benzyl-D-galactal 

Downstream Products

• 85395-79-5 2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-galactopyranosyl chloride 
• 148926-02-7 2-O-benzoyl-3,4,6-tri-O-benzyl-D-galactopyranose 
• 351900-98-6 O-4-methoxybenzyl-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-O-[(2,3,4-tri-O-benzoyl-β-D-xylosyl)-(1->3)]-6-O-methyl-4-O-acetyl-β-D-glucuronate 
• 351900-96-4 O-4-methoxybenzyl-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-6-O-methyl-4-O-acetyl-3-O-(tert-butyldimethylsilyl)-β-D-glucuronate 
• 850004-60-3 O-4-methoxybenzyl-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-O-[(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->3)]-6-O-methyl-4-O-acetyl-β-D-glucuronate 
• 850004-42-1 O-trichloroacetimidoyl-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-O-[(2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->3)]-6-O-methyl-4-O-acetyl-α-D-glucuronate 
• 351900-97-5 O-4-methoxybenzyl-O-[(2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1->2)]-6-O-methyl-4-O-acetyl-β-D-glucuronate 
• 68536-62-9 Benzoic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-cyclohexyloxy-tetrahydro-pyran-3-yl ester 
• 68536-62-9 2-O-benzoyl-1-O-cyclohexyl-3,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 68536-61-8 Benzoic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-isobutoxy-tetrahydro-pyran-3-yl ester 
• 73445-33-7 Benzoic acid (2R,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-isobutoxy-tetrahydro-pyran-3-yl ester 
• 40246-29-5 Benzoic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methoxy-tetrahydro-pyran-3-yl ester 
• 73445-32-6 methyl 2-O-benzoyl-3,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 73445-27-9 methyl 3,4,6-tri-O-benzyl-β-D-galactopyranoside 

Relevant academic research and scientific papers

Synthetic studies of complex immunostimulants from Quillaja saponaria: Synthesis of the potent clinical immunoadjuvant QS-21Aapi

QS-21 is one of the most promising new adjuvants for immune response potentiation and dose-sparing in vaccine therapy given its exceedingly high level of potency and its favorable toxicity profile. Melanoma, breast cancer, small cell lung cancer, prostate cancer, HIV-1, and malaria are among the numerous maladies targeted in more than 80 recent and ongoing vaccine therapy clinical trials involving QS-21 as a critical adjuvant component for immune response augmentation. QS-21 is a natural product immunostimulatory adjuvant, eliciting both T-cell- and antibody-mediated immune responses with microgram doses. Herein is reported the synthesis of QS-21 Aapi in a highly modular strategy, applying novel glycosylation methodologies to a convergent construction of the potent saponin immunostimulant. The chemical synthesis of QS-21 offers unique opportunities to probe its mode of biological action through the preparation of otherwise unattainable nonnatural saponin analogues.

THE USE OF 2-O-ACYL-1-O-SULFONYL-D-GALACTOPYRANOSE DERIVATIVES IN β-D-GALACTOPYRANOSIDE SYNTHESIS

Several 1-O-sulfonyl derivatives of D-galactopyranose having a participating benzoyl or p-methoxybenzoyl group at O-2 were synthesized from the corresponding D-galactopyranosyl chloride derivatives by use of silver p-toluenesulfonate or trifluoroethanesulfonate in acetonitrile.The reaction of the 1-O-sulfonyl-D-galactopyranose derivatives with several alcohols in various solvents at different times and temperatures served as reactions to determine the best conditions for synthesizing stereoselectively β-D-galactopyranosides in high yields.This method was used to prepare, in good yield, several β-D-galactopyranosyl-containing disaccharides.