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

Base Information

Chemical Name:tert-butyldimethylsilyl 2,3-di-O-benzoyl-6-phenylthio-6-deoxy-α/β-D-glucopyranoside
CAS No.:291774-72-6
Molecular Formula:C₃₂H₃₈O₇SSi
Molecular Weight:594.801
Hs Code.:

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

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Technology Process of tert-butyldimethylsilyl 2,3-di-O-benzoyl-6-phenylthio-6-deoxy-α/β-D-glucopyranoside

There total 1 articles about tert-butyldimethylsilyl 2,3-di-O-benzoyl-6-phenylthio-6-deoxy-α/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: 95.0%

: 882-33-7
diphenyldisulfane

: C₂₆H₃₄O₈Si

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

Guidance literature:: With tributylphosphine; In pyridine; at 20 ℃; for 24h;
DOI:10.1016/S0040-4020(01)00959-0

Reference yield:

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

: 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 2 steps

1.1: pyridine

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

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

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; pyridine; 1.1: Acetylation / 2.1: Substitution / 2.2: Addition;
DOI:10.1021/ol0062143

Reference yield:

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

: methyl (cholesterol-3-yl 4-O-acetyl-2,3-di-O-benzoyl-β-D-glucopyranoside)uronate

Guidance literature:: Multi-step reaction with 5 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

4.1: SO₂Cl₂; pyridine / CCl₄ / 0 °C

5.1: HgCl₂ / CHCl₃; H₂O / 20 °C

With pyridine; sulfuryl dichloride; 4 Angstroem MS; tetrabutyl ammonium fluoride; acetic acid; mercury dichloride; In tetrahydrofuran; pyridine; tetrachloromethane; dichloromethane; chloroform; water; 1.1: Acetylation / 2.1: Substitution / 2.2: Addition / 3.1: Substitution / 3.2: Substitution / 4.1: Chlorination / 5.1: Substitution;
DOI:10.1021/ol0062143