benzyl 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-6-O-(t-butyldiphenylsilyl)-β-D-glucopyranoside

Base Information

Chemical Name:benzyl 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-6-O-(t-butyldiphenylsilyl)-β-D-glucopyranoside
CAS No.:476313-35-6
Molecular Formula:C₄₅H₄₇ClO₈Si
Molecular Weight:779.402
Hs Code.:

Synonyms:benzyl 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-6-O-(t-butyldiphenylsilyl)-β-D-glucopyranoside

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Chemical Property of benzyl 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-6-O-(t-butyldiphenylsilyl)-β-D-glucopyranoside

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Technology Process of benzyl 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-6-O-(t-butyldiphenylsilyl)-β-D-glucopyranoside

There total 8 articles about benzyl 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-6-O-(t-butyldiphenylsilyl)-β-D-glucopyranoside 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: 97.0%

: 100-51-6,185532-71-2
benzyl alcohol

: 476313-23-2
methyl 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-6-O-(t-butyldiphenylsilyl)-1-thio-β-D-glucopyranoside

: 476313-35-6
benzyl 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-6-O-(t-butyldiphenylsilyl)-β-D-glucopyranoside

Guidance literature:: With N-iodo-succinimide; triethylsilyl trifluoromethyl sulfonate; In dichloromethane; at -20 ℃;
DOI:10.1021/ja020781z

Reference yield:

: 98-88-4
benzoyl chloride

: 476313-35-6
benzyl 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-6-O-(t-butyldiphenylsilyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 75 percent / DMAP; pyridine / 80 °C

2: BH₃*NMe₃; AlCl₃; MS 4A / CH₂Cl₂; diethyl ether / 4 h / 0 °C

3: 13.85 g / Et₃N; DMAP / CH₂Cl₂ / 20 °C

4: 92 percent / pyridine / CH₂Cl₂ / 0 °C

5: 97 percent / NIS; TESOTf / CH₂Cl₂ / -20 °C

With pyridine; dmap; N-iodo-succinimide; aluminium trichloride; trimethylamine-borane; triethylsilyl trifluoromethyl sulfonate; triethylamine; In diethyl ether; dichloromethane;
DOI:10.1021/ja020781z

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 476313-35-6
benzyl 2-O-benzoyl-4-O-benzyl-3-O-chloroacetyl-6-O-(t-butyldiphenylsilyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 13.85 g / Et₃N; DMAP / CH₂Cl₂ / 20 °C

2: 92 percent / pyridine / CH₂Cl₂ / 0 °C

3: 97 percent / NIS; TESOTf / CH₂Cl₂ / -20 °C

With pyridine; dmap; N-iodo-succinimide; triethylsilyl trifluoromethyl sulfonate; triethylamine; In dichloromethane;
DOI:10.1021/ja020781z