1053736-23-4

Basic information

• Product Name: (2R,3R,4S,5R,6S)-2-Benzyloxymethyl-4-((2S,3R,4S,5R,6R)-3,4-bis-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-6-phenylsulfanyl-tetrahydro-pyran-3,5-diol
• CAS NO: 1053736-23-4
• Molecular Weight: 794.963
• Mol File: 1053736-23-4.mol

Chemical Properties

• CAS DataBase Reference: (2R,3R,4S,5R,6S)-2-Benzyloxymethyl-4-((2S,3R,4S,5R,6R)-3,4-bis-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-6-phenylsulfanyl-tetrahydro-pyran-3,5-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R,4S,5R,6S)-2-Benzyloxymethyl-4-((2S,3R,4S,5R,6R)-3,4-bis-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-6-phenylsulfanyl-tetrahydro-pyran-3,5-diol(1053736-23-4)
• EPA Substance Registry System: (2R,3R,4S,5R,6S)-2-Benzyloxymethyl-4-((2S,3R,4S,5R,6R)-3,4-bis-benzyloxy-6-benzyloxymethyl-5-hydroxy-tetrahydro-pyran-2-yloxy)-6-phenylsulfanyl-tetrahydro-pyran-3,5-diol(1053736-23-4)

Safety Data

• Hazardous Substances Data: 1053736-23-4(Hazardous Substances Data)

Upstream product

• 205590-25-6 phenyl 3'-O-benzyl-2,2':4,6:4',6'-tri-O-benzylidene-1-thio-β-laminaribioside 

Relevant articles and documents

Interglycosidic Acetals IV. Preparation and Regioselective Cleavage of Phenyl 2,2′ : 4,6:4′,6′-Tri-O-benzylidene-l-thio-β-laminaribiosides

A (+)-10-Camphorsulfonic acid-catalysed acetal exchange reaction of phenyl 1-thio-β-laminaribioside using 3.5 molar equivalents of α,α-dimethoxytoluene gave a tris(benzylidene acetal), which was isolated and characterized as phenyl 3′-O-acetyl-2,2′ 4,6:4′6′-tri-O-benzylidene-1-thio-β-laminaribioside, and the corresponding 3′-O-benzyl derivative 6. Upon a treatment with pyridinium p-toluenesulfonate, the interglycosidic 2,2′-acetal in 6 underwent selective cleavage to give the 2,2′-diol. Additionally, a reductive ring-opening reaction of 6 with lithium aluminium hydride/anhydrous aluminium chloride, followed by O-acetylation, gave the 2,6,6′-O-acetyl-4,2',3',4'-tetra-0-benzyl derivative in 73% yield. A different regioselectivity was observed in the reduction of 6 with borane-trimethylamine adduct/anhydrous aluminium chloride or sodium cyanotrihydroborate/methanesulfonic acid, giving the corresponding 2,4,4′-triol as the major product.