210833-99-1

Basic information

• Product Name: phenyl 2,3,4-tri-O-benzyl-1-thio-D-glucopyranoside
• Synonyms: phenyl 2,3,4-tri-O-benzyl-1-thio-D-glucopyranoside
• CAS NO: 210833-99-1
• Molecular Weight: 542.696
• Mol File: 210833-99-1.mol

Chemical Properties

• CAS DataBase Reference: phenyl 2,3,4-tri-O-benzyl-1-thio-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 2,3,4-tri-O-benzyl-1-thio-D-glucopyranoside(210833-99-1)
• EPA Substance Registry System: phenyl 2,3,4-tri-O-benzyl-1-thio-D-glucopyranoside(210833-99-1)

Safety Data

• Hazardous Substances Data: 210833-99-1(Hazardous Substances Data)

Upstream product

• 498-07-7 levoglucosan 
• 100-39-0 benzyl bromide 
• 4551-15-9 phenylthiotrimethylsilane 
• 10548-46-6 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose 

Downstream Products

• 259742-00-2 Phthalic acid mono-((2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester 
• 120403-26-1 phenyl 2,3,4-tri-O-benzyl-1-thio-α-D-glucopyranoside 
• 259742-10-4 Phthalic acid 1-[(2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-3-(2,2,2-trichloro-ethoxycarbonyloxy)-tetrahydro-pyran-2-ylmethyl] ester 2-((2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester 
• 259742-16-0 Benzoic acid (2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-2-[di-tert-butyl-((2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethoxy)-silanyloxymethyl]-6-methoxy-tetrahydro-pyran-3-yl ester 
• 259742-04-6 Phthalic acid 1-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl) ester 2-((2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl) ester 
• 139299-89-1 phenyl 2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranoside 
• 210834-00-7 phenyl 6-O-(4-azido-3-chlorobenzyl)-2,3,4-tri-O-benzyl-1-thio-D-glucopyranoside 

Relevant articles and documents

Rapid Synthesis of l-Idosyl Glycosyl Donors from α-Thioglucosides for the Preparation of Heparin Disaccharides

A new methodology for the synthesis of the most challenging heparin building block has been developed. Orthogonally protected l-idosyl glycosyl donors were prepared by C5 epimerization of the corresponding thioglucosides using the hydroboration/oxidation method followed by a 4,6-acetal formation. The α-anomeric configuration was crucial, and the bulky C4 substituent was advantageous for the high l-ido diastereoselectivity. The 4,6-arylmethylene group proved to be a directing element in glycosylation, whereby stereoselective α-idosylation could be achieved by using idosyl donors without a C-2 participating group.

Stereoselective glycosylation and oligosaccharide synthesis on solid support using a 4-azido-3-chlorobenzyl group for temporary protection

A versatile and practical methodology for solid-phase synthesis was elaborated in the synthesis of α(1→6)- and β(1→6)linked oligoglucoses by using thioglycosides having a 4-azido-3-chlorobenzyl (ClAzb) group for temporary protection of hydroxy functions.

Azidohalogenobenzyl derivatives, sugar compounds and protection of hydroxy groups

Azidohalogenobenzyl derivatives of the formula (I) STR1 wherein A is a halogen atom, B is a halogen atom or a hydrogen atom, and X is a group reactive with a hydroxy group, methods of protecting hydroxy group(s) using said derivatives, and sugar compounds wherein a hydrogen atom of at least one hydroxy group is substituted by an azidohalogenobenzyl group. According to the present invention, there are provided novel derivatives capable of introducing a group into a compound having hydroxy group(s), which group is useful as a stable hydroxy-protecting group even in solid phase synthesis for the purpose of the extension of sugar chain under continuous acidic conditions and of being removed under mild conditions; sugar compounds protected by using said derivatives; and methods of protecting hydroxy group(s) using said derivatives.