175910-00-6

Basic information

• Product Name: (2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carbaldehyde
• CAS NO: 175910-00-6
• Molecular Weight: 1015.21
• Mol File: 175910-00-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carbaldehyde(175910-00-6)
• EPA Substance Registry System: (2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tetrahydro-pyran-2-carbaldehyde(175910-00-6)

Safety Data

• Hazardous Substances Data: 175910-00-6(Hazardous Substances Data)

Upstream product

• 160584-11-2 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-(2-thiazolyl)-α-D-galactopyranose 
• 160584-12-3 1-O-Acetyl-2,3,4,6-tetra-O-benzyl-1-(2-thiazolyl)-β-D-galactopyranose 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 

Relevant articles and documents

Thiazolylketol acetates as glycosyl donors. Stereoselective synthesis of α-linked ketodisaccharides

TMSOTf-promoted glycosidation of 1-C-(2-thiazolyl)-α-D-galactopyranosyl acetate (α)-2 and 1-C-(2-thiazolyl)-α-D-mannofuranosyl acetate 7 donors with 1 equiv of primary 3 and secondary 5 sugar alcohols acceptors gave exclusively the corresponding α-D-ketodisaccharides 4a, 8a, 11a, and 12a in 60-73% yield. On the other hand glycosidation of the 1-C-(2-thiazolyl)-α-D-glucopyranosyl acetate 6 with the primary alcohol 3 under the above conditions afforded a mixture of α- and β-D-ketodisaccharides 9a and 10a in ca. 1:1 ratio. The important role of the thiazole ring for the easy glycosidation of these ketol acetates was pointed out by comparison with ketoses bearing a methyl, carboxymethyl, and 2-furyl group. Application of the thiazolyl-to-formyl deblocking reaction sequence to the thiazolylketodisaccharides gave the corresponding aldehydes which in turn were converted into alcohols and esters by reduction and oxidation, respectively.