2,3-di-O-benzoyl-4-O-acetyl-6-phenylthio-6-deoxy-α-D-glucopyranosyl trichloroacetimidate

Base Information

Chemical Name:2,3-di-O-benzoyl-4-O-acetyl-6-phenylthio-6-deoxy-α-D-glucopyranosyl trichloroacetimidate
CAS No.:291774-73-7
Molecular Formula:C₃₀H₂₆Cl₃NO₈S
Molecular Weight:666.963
Hs Code.:

Synonyms:2,3-di-O-benzoyl-4-O-acetyl-6-phenylthio-6-deoxy-α-D-glucopyranosyl trichloroacetimidate

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Chemical Property of 2,3-di-O-benzoyl-4-O-acetyl-6-phenylthio-6-deoxy-α-D-glucopyranosyl trichloroacetimidate

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Technology Process of 2,3-di-O-benzoyl-4-O-acetyl-6-phenylthio-6-deoxy-α-D-glucopyranosyl trichloroacetimidate

There total 5 articles about 2,3-di-O-benzoyl-4-O-acetyl-6-phenylthio-6-deoxy-α-D-glucopyranosyl trichloroacetimidate 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:

: 545-06-2
trichloroacetonitrile

: 291774-88-4
tert-butyldimethylsilyl 4-O-acetyl-2,3-di-O-benzoyl-6-phenylthio-6-deoxy-α-D-glucopyranoside

: 291774-73-7
2,3-di-O-benzoyl-4-O-acetyl-6-phenylthio-6-deoxy-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: tert-butyldimethylsilyl 4-O-acetyl-2,3-di-O-benzoyl-6-phenylthio-6-deoxy-α-D-glucopyranoside; With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 10h;

trichloroacetonitrile; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 1h; Further stages.;
DOI:10.1021/ol0062143

Reference yield:

: 545-06-2
trichloroacetonitrile

: C₂₈H₂₆O₈S

: 291774-73-7
2,3-di-O-benzoyl-4-O-acetyl-6-phenylthio-6-deoxy-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1016/S0040-4020(01)00959-0

Reference yield:

: 882-33-7
diphenyldisulfane

: 291774-73-7
2,3-di-O-benzoyl-4-O-acetyl-6-phenylthio-6-deoxy-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 95 percent / n-Bu₃P / pyridine / 24 h / 20 °C

2.1: pyridine

3.1: HOAc; TBAF / tetrahydrofuran / 10 h / 20 °C

3.2: 545 mg / DBU / CH₂Cl₂ / 1 h / 20 °C

With tributylphosphine; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; pyridine; 1.1: Substitution / 2.1: Acetylation / 3.1: Substitution / 3.2: Addition;
DOI:10.1021/ol0062143