90124-30-4

Basic information

• Product Name: methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• Synonyms: methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• CAS NO: 90124-30-4
• Molecular Weight: 937.992
• Mol File: 90124-30-4.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside(90124-30-4)
• EPA Substance Registry System: methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside(90124-30-4)

Safety Data

• Hazardous Substances Data: 90124-30-4(Hazardous Substances Data)

Upstream product

• 108999-05-9 methyl 2,3,4-tri-O-benzyl-6-O--α-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 167084-05-1 methyl S-4-methylphenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosidonate 
• 67670-69-3 N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 
• 108999-04-8 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,3-dibromo-2,3,5-trideoxy-β-D-erythro-L-manno-non-2-ulopyranosonate 
• 73960-72-2 methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 
• 20298-35-5 N-acetylneuraminic acid methyl ester 
• 6813-81-6 N-acetyl neuraminic acid 
• 109901-79-3 methyl 2,3,4-tri-O-benzyl-6-O--α-D-glucopyranoside 
• 109681-20-1 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,3-anhydro-5-deoxy-β-D-erythro-L-gluco-non-2-ulopyranosonate 
• 84380-10-9 4,7,8,9-tetra-O-acetyl-N-acetylneuraminic acid methyl ester 
• 6931-68-6 methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 
• 118977-25-6 methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycerol-β-D-galactonon-2-ulopyranoside)onate 
• 104652-19-9 methyl (dodecyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosid)onate 

Relevant articles and documents

Donor-Reactivity-Controlled Sialylation Reactions

Although tremendous efforts have been made for the efficient preparation of sialosides, controlling the stereochemical outcome of sialylation reaction still remains one of the most challenging tasks due to the unique chemical structure of sialic acid. We developed a new strategy to statistically analyze the stereoselectivity of sialylation reactions on six types of p-tolyl thiosialosides in NIS/TfOH system using Relative Reactivity Value (RRV) as the indicator. Analysis of the reaction mechanism showed the formation of the relatively stable glycosyl bromide and glycosyl chloride intermediates from halide- and triflate-containing promotors in the absence of an acceptor. We found that the α/β-stereoselectivity, yields, and intermediate changes were associated with their donor reactivity. These findings enable to tailor the most suitable building blocks for stereo-controlled sialylation reactions.

Synthesis of a useful lauryl thioglycoside of sialic acid and its application

An efficient synthesis of a useful thioglycosyl donor 2 was accomplished directly from known peracetylated sialic acid methyl ester and 1-dodecanethiol (lauryl mercaptan) in the presence of BF3-OEt2. The reactivities of the lauryl glycosides for glycosidation by means of TMSOTf as a convenient promoter were investigated, and the lauryl thioglycoside showed satisfactory activities. Further transformation of the lauryl glycoside was also attempted to give a 5-azide analogue 14 of the sialic acid, which was also reacted with a secondary alcohol in the presence of TMSOTf to give known glycoside 15 in high yield.

Efficient Sialylation with Phenyltrifluoroacetimidates as Leaving Groups

(Matrix presented) Sialylation with N-phenyltrifluoroacetimidates as leaving groups and a catalytic amount of TMSOTf as promoter compares favorably with the previous protocols for direct sialylation and expand in essence the scope of the Schmidt glycosyla