1-S-acetyl-2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranose

Base Information

Chemical Name:1-S-acetyl-2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranose
CAS No.:273935-04-9
Molecular Formula:C₄₅H₅₀O₆SSi
Molecular Weight:747.04
Hs Code.:

Synonyms:1-S-acetyl-2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranose

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Chemical Property of 1-S-acetyl-2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranose

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Technology Process of 1-S-acetyl-2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranose

There total 5 articles about 1-S-acetyl-2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranose 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: 82.0%

: 507-09-5
tiolacetic acid

: 273935-03-8
2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-glucopyranosyl trichloroacetamidate

: 273935-04-9
1-S-acetyl-2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranose

Guidance literature:: In dichloromethane; at 20 ℃; for 12h;
DOI:10.1016/S0008-6215(99)00327-4

Reference yield:

: 78184-40-4
1-O-allyl-2,3,4-tri-O-benzyl-α-D-glucopyranoside

: 273935-04-9
1-S-acetyl-2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 4 steps

1.1: 94 percent / triethilamine; 4-dimethoxyaminopyridine / CH₂Cl₂ / 3 h / 20 °C

2.1: DABCO / RhCl(PPh₃)3 / aq. ethanol / 6 h / Heating

2.2: 85 percent / I₂; H₂O / pyridine / 0.17 h / 20 °C

3.1: 81 percent / DBU / CH₂Cl₂ / 4 h

4.1: 82 percent / CH₂Cl₂ / 12 h / 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; N,N-dimethoxy-4-amino-pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; RhCl(PPh₃)3; In ethanol; dichloromethane; 1.1: silylation / 2.1: Isomerization / 2.2: Hydrolysis / 3.1: Addition / 4.1: Substitution;
DOI:10.1016/S0008-6215(99)00327-4

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 273935-04-9
1-S-acetyl-2,3,4-tri-O-benzyl-6-O-tert-butyldiphenylsilyl-1-thio-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 4 steps

1.1: 94 percent / triethilamine; 4-dimethoxyaminopyridine / CH₂Cl₂ / 3 h / 20 °C

2.1: DABCO / RhCl(PPh₃)3 / aq. ethanol / 6 h / Heating

2.2: 85 percent / I₂; H₂O / pyridine / 0.17 h / 20 °C

3.1: 81 percent / DBU / CH₂Cl₂ / 4 h

4.1: 82 percent / CH₂Cl₂ / 12 h / 20 °C

With 1,4-diaza-bicyclo[2.2.2]octane; N,N-dimethoxy-4-amino-pyridine; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; RhCl(PPh₃)3; In ethanol; dichloromethane; 1.1: silylation / 2.1: Isomerization / 2.2: Hydrolysis / 3.1: Addition / 4.1: Substitution;
DOI:10.1016/S0008-6215(99)00327-4