120255-47-2

Basic information

• Product Name: (2S,3S,4R,5R,6S)-4-Benzyloxy-2-methyl-6-methylsulfanyl-tetrahydro-pyran-3,5-diol
• Synonyms: (2S,3S,4R,5R,6S)-4-Benzyloxy-2-methyl-6-methylsulfanyl-tetrahydro-pyran-3,5-diol
• CAS NO: 120255-47-2
• Molecular Weight: 284.376
• Mol File: 120255-47-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3S,4R,5R,6S)-4-Benzyloxy-2-methyl-6-methylsulfanyl-tetrahydro-pyran-3,5-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S,4R,5R,6S)-4-Benzyloxy-2-methyl-6-methylsulfanyl-tetrahydro-pyran-3,5-diol(120255-47-2)
• EPA Substance Registry System: (2S,3S,4R,5R,6S)-4-Benzyloxy-2-methyl-6-methylsulfanyl-tetrahydro-pyran-3,5-diol(120255-47-2)

Safety Data

• Hazardous Substances Data: 120255-47-2(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 115678-08-5 methyl 1-thio-α-L-rhamnopyranoside 

Downstream Products

• 151967-77-0 methyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-O-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside 
• 151967-75-8 methyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside 
• 151967-76-9 O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl chloride 
• 145836-01-7 Methyl 2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside 
• 151967-72-5 methyl 2,4-di-O-benzoyl-3-O-benzyl-1-thio-α-L-rhamnopyranosid 

Relevant articles and documents

Di- and tri-saccharide glycosyl donors for the synthesis of fragments of the O-specific antigen of Shigella dysenteriae type 1

Methyl O-(2,4-di-O-benzoyl-3-O-bromoacetyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside was treated with dichloromethyl methyl ether and ZnCl2 to give O-(2,4-di-O-benzoyl-3-O-bromoacetyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl chloride.Similar treatment of methyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside (13) gave crystalline O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-α-L-rhamnosyl chloride (14), which was also obtained by treatment of methyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside (12) with chlorine.In contrast to the conversion 12 -> 14, which was stereospecific, the reaction of methyl O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->3)-(O-2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside with chlorine gave a mixture of the corresponding α- (16) and (β)- 17 glycosyl chlorides.Condensation of the mixed chlorides 16 and 17 with 1,3,4,6-tetra-O-acetyl-α-D-galactopyranose, followed by reduction-acetylation of the product, gave a fully protected derivative of the tetrasaccharide of α-D-GlcpNAc-(1->3)-α-L-Rhap-(1->3)-α-L-Rhap-(1->2)-α-D-Galp.