145836-01-7

Basic information

• Product Name: Methyl 2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside
• Synonyms: Methyl 2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside
• CAS NO: 145836-01-7
• Molecular Weight: 402.468
• Mol File: 145836-01-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Methyl 2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside(145836-01-7)
• EPA Substance Registry System: Methyl 2,4-di-O-benzoyl-1-thio-α-L-rhamnopyranoside(145836-01-7)

Safety Data

• Hazardous Substances Data: 145836-01-7(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 115678-08-5 methyl 1-thio-α-L-rhamnopyranoside 
• 707-07-3 orthobenzoic acid trimethyl ester 
• 151967-74-7 methyl 2,4-di-O-benzoyl-3-O-(4-methoxybenzyl)-1-thio-α-L-rhamnopyranoside 
• 151967-73-6 (2S,3S,4R,5R,6S)-4-(4-Methoxy-benzyloxy)-2-methyl-6-methylsulfanyl-tetrahydro-pyran-3,5-diol 
• 120255-47-2 (2S,3S,4R,5R,6S)-4-Benzyloxy-2-methyl-6-methylsulfanyl-tetrahydro-pyran-3,5-diol 
• 151967-72-5 methyl 2,4-di-O-benzoyl-3-O-benzyl-1-thio-α-L-rhamnopyranosid 

Downstream Products

• 146934-40-9 1-(Trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-(2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 
• 146934-41-0 1-(Trimethylsilyl)ethyl 2,4-di-O-benzoyl-3-O-(2,4-di-O-benzoyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 
• 146934-39-6 2,4-di-O-benzoyl-3-O-chloroacetyl-α-L-rhamnopyranosyl chloride 
• 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 
• 151967-76-9 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 
• 160529-59-9 O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzoyl-α-L-rhamnopyranosyl bromide 
• 146934-38-5 Methyl 2,4-di-O-benzoyl-3-O-chloroacetyl-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 

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.

Synthesis of tetrasaccharide building block of the O-specific polysaccharide of Shigella dysenteriae type 1

A glycosyl trichloroacetimidate derivative (1) of the tetrasaccharide α-D-Galp-(1→3)-α-D-GlcpNAc-(1→3)-α-L-Rhap-(1→3)-α-L-Rhap was synthesized in a highly stereoselective, stepwise manner, using methyl 1-thioglycosides of L-rhamnose, 2-azido-2-deoxy-D-glucose and D-galactose, as major intermediates. The protecting group scenario in compound 1 permits regioselective deblocking at its 'non-reducing end' unit. Therefore 1 is a suitable intermediate for the preparation of extended fragments of the title polysaccharide.