methyl (5-benzyloxyacetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)onate-(2→3)-p-toluyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Base Information

Chemical Name:methyl (5-benzyloxyacetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)onate-(2→3)-p-toluyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside
CAS No.:1453169-43-1
Molecular Formula:C₅₃H₅₅NO₁₉S
Molecular Weight:1042.08
Hs Code.:

methyl (5-benzyloxyacetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)onate-(2→3)-p-toluyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

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Chemical Property of methyl (5-benzyloxyacetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)onate-(2→3)-p-toluyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

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Technology Process of methyl (5-benzyloxyacetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)onate-(2→3)-p-toluyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

There total 4 articles about methyl (5-benzyloxyacetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)onate-(2→3)-p-toluyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: methyl (5-benzyloxyacetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-2-(dibutylphosphoryl)-3,5-dideoxy-D-glycero-D-galacto-non-2-ulopyranoside)onate

: 220645-55-6
p-methylphenyl 2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

: 1453169-42-0
methyl (5-benzyloxyacetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosyl)onate-(2→3)-p-toluyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

: 1453169-43-1
methyl (5-benzyloxyacetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)onate-(2→3)-p-toluyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -78 ℃; for 1h; Overall yield = 43%; Overall yield = 0.094 g; diastereoselective reaction; Inert atmosphere; Molecular sieve;
DOI:10.1002/ejoc.201300664

Reference yield:

: 1453169-68-0
methyl p-tolyl 7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-5-(N-benzyloxyacetamido)-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonlopyranosonate

: 1453169-42-0
methyl (5-benzyloxyacetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosyl)onate-(2→3)-p-toluyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

: 1453169-43-1
methyl (5-benzyloxyacetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)onate-(2→3)-p-toluyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: N-iodo-succinimide; trifluorormethanesulfonic acid / dichloromethane / 5 h / 0 °C / Molecular sieve; Inert atmosphere

2: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere; Molecular sieve

With N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; In dichloromethane;
DOI:10.1002/ejoc.201300664

Reference yield:

: 19810-31-2
Benzyloxyacetyl chloride

: 1453169-42-0
methyl (5-benzyloxyacetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosyl)onate-(2→3)-p-toluyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

: 1453169-43-1
methyl (5-benzyloxyacetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)onate-(2→3)-p-toluyl-2-O-benzoyl-4,6-O-benzylidene-1-thio-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

2: N-iodo-succinimide; trifluorormethanesulfonic acid / dichloromethane / 5 h / 0 °C / Molecular sieve; Inert atmosphere

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -78 °C / Inert atmosphere; Molecular sieve

With N-iodo-succinimide; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1002/ejoc.201300664