91602-61-8

Basic information

• Product Name: phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside
• CAS NO: 91602-61-8
• Molecular Weight: 632.821
• Mol File: 91602-61-8.mol
• Article Data: 21

Chemical Properties

• CAS DataBase Reference: phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside(91602-61-8)
• EPA Substance Registry System: phenyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-mannopyranoside(91602-61-8)

Safety Data

• Hazardous Substances Data: 91602-61-8(Hazardous Substances Data)

Upstream product

• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 14365-16-3 bis-(phenylthio)-dibutylstannane 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 108-98-5 thiophenol 
• 30608-21-0 1-O-trimethylsilyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 78890-59-2 Methoxy-acetic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 19488-61-0 methyl 2,3,4,6-tetra-O-benzyl α-D-glucopyranoside 
• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 144-55-8 sodium hydrogencarbonate 
• 882-33-7 diphenyldisulfane 
• 998-40-3 tributylphosphine 
• 85982-88-3 1-O-trimethylsilyl-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 

Downstream Products

• 97321-70-5 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-β-D-manno-hept-1-enitol 
• 388570-21-6 3,4,5,7-tetra-O-benzyl-α-D-glycero-D-lyxo-hept-2-ulopyranose 
• 25320-59-6 tetra-O-benzyl glucopyranosyl chloride 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 165680-85-3 methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 130050-83-8 methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 77117-44-3 methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 64694-18-4 methyl 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-α-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.

Ni-Catalyzed Suzuki-Miyaura Cross-Coupling of α-Oxo-vinylsulfones to Prepare C-Aryl Glycals and Acyclic Vinyl Ethers

We demonstrate that readily available and bench-stable α-oxo-vinylsulfones are competent electrophiles in Ni-catalyzed Suzuki-Miyaura cross-coupling reactions. The C-sulfone bond in the α-oxo-vinylsulfone motif is cleaved chemoselectively in these reactions, furnishing C-aryl glycals or acyclic vinyl ethers in high yields. These reactions proceed under mild conditions and tolerate a remarkable scope of heterocycles and functional groups. Preliminary mechanistic studies revealed the importance of an α-heteroatom in facilitating these transformations.

Dissection of the effects that govern thioglucoside and thiomannoside reactivity

Neighboring group effects were investigated in gluco- and manno-configured thioglycosides under NIS/TfOH activation. Donors possessing a 2-O-benzoyl group that are capable (1,2-trans) and incapable (1,2-cis) of exerting nucleophilic push were compared wit