183875-29-8

Basic information

• Product Name: b-D-Galactopyranoside, phenyl 3,4,6-tris-O-(phenylMethyl)-1-thio-
• Synonyms: b-D-Galactopyranoside, phenyl 3,4,6-tris-O-(phenylMethyl)-1-thio-
• CAS NO: 183875-29-8
• Molecular Formula: C₃₃H₃₄O₅S
• Molecular Weight: 542.68506
• Mol File: 183875-29-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: b-D-Galactopyranoside, phenyl 3,4,6-tris-O-(phenylMethyl)-1-thio-(CAS DataBase Reference)
• NIST Chemistry Reference: b-D-Galactopyranoside, phenyl 3,4,6-tris-O-(phenylMethyl)-1-thio-(183875-29-8)
• EPA Substance Registry System: b-D-Galactopyranoside, phenyl 3,4,6-tris-O-(phenylMethyl)-1-thio-(183875-29-8)

Safety Data

• Hazardous Substances Data: 183875-29-8(Hazardous Substances Data)

Upstream product

• 183875-28-7 phenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside 
• 68779-52-2 1,2-O-(1-methoxyethylidene)-3,4,6-tri-O-benzyl-α-D-galactopyranose 
• 108-98-5 thiophenol 
• 4551-15-9 phenylthiotrimethylsilane 
• 80040-79-5 3,4,6-tri-O-benzyl-D-galactal 
• 94-99-5 2,4-Dichlorobenzyl chloride 
• 21193-75-9 D-galactal 
• 930-69-8 sodium thiophenolate 
• 100-39-0 benzyl bromide 
• 77790-46-6 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-β-D-galactopyranose 

Downstream Products

• 183875-30-1 2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-phenylsulfanyl-tetrahydro-pyran-3-yl ester 
• 213185-35-4 phenyl 3,4,6-tri-O-benzyl-2-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside 
• 259871-00-6 phenyl 3,4,6-tri-O-benzyl-2-O-(3-carboxypropionyl)-1-thio-β-D-galactopyranoside 

Relevant articles and documents

C-2 auxiliaries for stereoselective glycosylation based on common additive functional groups

The stereoselective introduction of the glycosidic bond is one of the main challenges in chemical oligosaccharide synthesis. Stereoselective glycosylation can be achieved using neighbouring group participation of a C-2 auxiliary or using additives, for example. Both methods aim to generate a defined reactive intermediate that reacts in a stereoselective manner with alcohol nucleophiles. This inspired us to develop new C-2 auxiliaries based on commonly used additive functionalities such as ethers, phosphine oxides and tertiary amides. Good 1,2-trans-selectivity was observed for the phosphine oxide and amide-based auxiliaries expanding the toolbox with new auxiliaries for stereoselective glycosylation reactions.

α-Selective Glycosylation with β-Glycosyl Sulfonium Ions Prepared via Intramolecular Alkylation

Stereoselective glycosylation remains the main challenge in the chemical synthesis of oligosaccharides. Herein we report a simple method to convert thioglycosides into β-sulfonium ions via an intramolecular alkylation reaction, leading to highly α-selective glycosylations for a variety of glycosyl acceptors. The influence of the thioglycoside substituent and the protecting group pattern on the glycosyl donor was investigated and showed a clear correlation with the observed stereoselectivity.

Prearranged glycosides. Part 8. Intramolecular α-galactosylation via succinoyl tethered glycosides

Benzyl protected phenyl 1-thio-galactopyranoside donors which were tethered by a succinoyl linker at their positions 2 and 6, respectively, to position 3 of a blocked benzyl glucopyranoside acceptor with a 4-OH group solely afforded the corresponding α-(1→4)-linked disaccharides upon intramolecular glycosylation. 4,6-Siloxane protected mannosides react with rearrangement of the siloxane group under similar conditions.

Synthesis of glycoconjugate vaccines against Shigella dysenteriae type 1

Syntheses of hexadecasaccharide and smaller fragments corresponding to one-four repeating units of the O-specific polysaccharide of Shigella dysenteriae type 1 are reported in a reactive aglycon-linked from. Two tetrasaccharide donor/acceptor repeating units were assembled from monosaccharide precursors in a stepwise fashion and used in a linear, iterative manner to construct the higher-membered saccharides using Schmidt's glycosylation technique that proved superior to others tested. Single-point attachment of the saccharides to human serum albumin, using a secondary heterobifunctional spacer, afforded a range of glycoconjugates for a detailed evaluation of their immunological characteristics.

Generalizing glycosylation: Synthesis of the blood group antigens Lea, Leb, and Le(x) using a standard set of reaction conditions

Because there are no general reaction conditions for any glycosylation method, biologically interesting oligosaccharides can only be made in a small number of laboratories in the world. To make carbohydrate synthesis accessible to nonspecialists, it is critical to have glycosylation methods that will work in a wide range of cases under a single set of conditions. The Lewis blood group antigens have attracted the attention of numerous synthetic carbohydrate groups because of their structural complexity. Although they have been synthesized many times, they have never been made using a single glycosylation method under one set of reaction conditions. In this paper, we show that the sulfoxide glycosylation method can be used to form all of the glycosidic linkages in the Lewis blood group antigens Lea (1), Leb (2), and Le(x) (3) stereoselectively under a uniform set of reaction conditions. This work highlights the flexibility of the sulfoxide method and demonstrates its utility for constructing families of related oligosaccharides.