cholesterol-3β-yl 4-O-acetyl-2,3-di-O-benzoyl-6-S-phenyl-6-thio-β-D-glucopyranoside

Base Information

Chemical Name:cholesterol-3β-yl 4-O-acetyl-2,3-di-O-benzoyl-6-S-phenyl-6-thio-β-D-glucopyranoside
CAS No.:291774-77-1
Molecular Formula:C₅₅H₇₀O₈S
Molecular Weight:891.222
Hs Code.:

Synonyms:cholesterol-3β-yl 4-O-acetyl-2,3-di-O-benzoyl-6-S-phenyl-6-thio-β-D-glucopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of cholesterol-3β-yl 4-O-acetyl-2,3-di-O-benzoyl-6-S-phenyl-6-thio-β-D-glucopyranoside

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Technology Process of cholesterol-3β-yl 4-O-acetyl-2,3-di-O-benzoyl-6-S-phenyl-6-thio-β-D-glucopyranoside

There total 6 articles about cholesterol-3β-yl 4-O-acetyl-2,3-di-O-benzoyl-6-S-phenyl-6-thio-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: 82.0%

: 57-88-5
cholesterol

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

: 291774-77-1
cholesterol-3β-yl 4-O-acetyl-2,3-di-O-benzoyl-6-S-phenyl-6-thio-β-D-glucopyranoside

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -50 ℃; for 0.5h;
DOI:10.1016/S0040-4020(01)00959-0

Reference yield:

: 882-33-7
diphenyldisulfane

: 291774-77-1
cholesterol-3β-yl 4-O-acetyl-2,3-di-O-benzoyl-6-S-phenyl-6-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 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

4.1: 4 Angstroem MS / CH₂Cl₂ / 0.5 h / 20 °C

4.2: 82 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -50 °C

With tributylphosphine; 4 Angstroem MS; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; pyridine; dichloromethane; 1.1: Substitution / 2.1: Acetylation / 3.1: Substitution / 3.2: Addition / 4.1: Substitution / 4.2: Substitution;
DOI:10.1021/ol0062143

Reference yield:

: 291774-72-6
tert-butyldimethylsilyl 2,3-di-O-benzoyl-6-phenylthio-6-deoxy-α/β-D-glucopyranoside

: 291774-77-1
cholesterol-3β-yl 4-O-acetyl-2,3-di-O-benzoyl-6-S-phenyl-6-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: pyridine

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

2.2: 545 mg / DBU / CH₂Cl₂ / 1 h / 20 °C

3.1: 4 Angstroem MS / CH₂Cl₂ / 0.5 h / 20 °C

3.2: 82 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -50 °C

With 4 Angstroem MS; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; pyridine; dichloromethane; 1.1: Acetylation / 2.1: Substitution / 2.2: Addition / 3.1: Substitution / 3.2: Substitution;
DOI:10.1021/ol0062143