38184-10-0

Basic information

• Product Name: .beta.-D-Glucopyranoside, phenyl 2,3,4,6-tetrakis-O-(phenylmethyl)-1-thio-
• Synonyms: .beta.-D-Glucopyranoside, phenyl 2,3,4,6-tetrakis-O-(phenylmethyl)-1-thio-;Phenyl2,3,4,6-tetra-O-benzyl-b-D-thioglucopyranoside;phenyl 2,3,4,6-tetra-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside;(2R,3R,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-(phenylthio)tetrahydro-2H-pyran
• CAS NO: 38184-10-0
• Molecular Formula: C₄₀H₄₀O₅S
• Molecular Weight: 632.81
• Mol File: 38184-10-0.mol
• Article Data: 51

Chemical Properties

• Appearance: /
• CAS DataBase Reference: .beta.-D-Glucopyranoside, phenyl 2,3,4,6-tetrakis-O-(phenylmethyl)-1-thio-(CAS DataBase Reference)
• NIST Chemistry Reference: .beta.-D-Glucopyranoside, phenyl 2,3,4,6-tetrakis-O-(phenylmethyl)-1-thio-(38184-10-0)
• EPA Substance Registry System: .beta.-D-Glucopyranoside, phenyl 2,3,4,6-tetrakis-O-(phenylmethyl)-1-thio-(38184-10-0)

Safety Data

• Hazardous Substances Data: 38184-10-0(Hazardous Substances Data)

Usage

Uses

Phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside (CAS# 38184-10-0) is a useful glycosylating agent and thioglycoside. Phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside is used in the synthetic preparation of macromolecules such as mycobacterium tuberculosis nonasaccharide.

Upstream product

• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 100-44-7 benzyl chloride 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 882-33-7 diphenyldisulfane 
• 108-98-5 thiophenol 
• 79386-43-9 diphenyl 2,3,4,6-tetra-O-benzyl-α-D-glucosyl phosphate 
• 100-39-0 benzyl bromide 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 604-69-3 β-D-glucose pentaacetate 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 84799-77-9 methyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 998-40-3 tributylphosphine 
• 144-55-8 sodium hydrogencarbonate 
• 2936-70-1 (2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 

Downstream Products

• 19488-61-0 methyl 2,3,4,6-tetra-O-benzyl α-D-glucopyranoside 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 56632-57-6 methyl O-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyll-α-D-glucopyranoside 
• 117307-17-2 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside sulfoxide 
• 157087-54-2 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-glucopyranoside sulfoxide 
• 59980-96-0 Trifluoro-methanesulfonic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 173395-55-6 (3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-5-((((3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-3aH-bis[1,3]dioxolo[4,5-b:4',5'-d]pyran 
• 86394-89-0 benzyl 2-O-benzyl-4,6-O-benzylidene-3-O-(tetra-O-benzyl-αβ-D-glucopyranosyl)-β-D-glucopyranoside 
• 216862-40-7 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-methyl-2-O-benzyl-4,6-O-benzylidene-α-D-mannopyranoside 
• 56632-55-4 cyclohexyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 56632-56-5 cyclohexyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 

Relevant articles and documents

Electrochemical Synthesis of Glycosyl Fluorides Using Sulfur(VI) Hexafluoride as the Fluorinating Agent

This manuscript describes the electrochemical synthesis of 17 different glycosyl fluorides in 73-98% yields on up to a 5 g scale that relies on the use of SF6 as an inexpensive and safe fluorinating agent. Cyclic voltammetry and related mechanistic studies carried out subsequently suggest that the active fluorinating species generated through the cathodic reduction of SF6 are transient under these reductive conditions and that the sulfur and fluoride byproducts are effectively scavenged by Zn(II) to generate benign salts.

How do Various Reaction Parameters Influence Anomeric Selectivity in Chemical Glycosylation with Thioglycosides and NIS/TfOH Activation?

The reaction of glycosyl donor phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside with NIS/TfOH(cat.) was systematically studied under various reaction conditions. Neither the molecular sieve pore size nor amount of NIS activator was found to have a

Visible Light Enables Aerobic Iodine Catalyzed Glycosylation

A versatile protocol for light induced catalytic activation of thioglycosides using iodine as an inexpensive and readily available photocatalyst was developed. Oxygen serves as a green and cost-efficient terminal oxidant and irradiation is performed with a common household LED-bulb. The scope of this glycosylation protocol was investigated in the synthesis of O-glycosides with yields up to 95 %.