phenyl 2,3-di-O-acetyl-4-O-chloroacetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2,3-di-O-acetyl-4-O-chloroacetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside
• CAS No.: 888012-98-4
• Molecular Formula: C₂₄H₃₅ClO₈SSi
• Molecular Weight: 547.142

Synonyms:phenyl 2,3-di-O-acetyl-4-O-chloroacetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside

Chemical Property of phenyl 2,3-di-O-acetyl-4-O-chloroacetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside

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Technology Process of phenyl 2,3-di-O-acetyl-4-O-chloroacetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside

There total 1 articles about phenyl 2,3-di-O-acetyl-4-O-chloroacetyl-6-O-tert-butyldimethylsilyl-1-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: 99.0%

phenyl 2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside + chloroacetyl chloride (79-04-9) → phenyl 2,3-di-O-acetyl-4-O-chloroacetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside (888012-98-4)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2006.03.002

Reference yield: 92.0%

phenyl 2,3-di-O-acetyl-4-O-chloroacetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside (888012-98-4) + 1-methyl-1H-imidazole (616-47-7) → 1-[(2R,3R,4S,5R,6S)-4,5-Diacetoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-phenylsulfanyl-tetrahydro-pyran-3-yloxycarbonylmethyl]-3-methyl-3H-imidazol-1-ium; chloride

Guidance literature:

In acetonitrile; at 80 ℃; for 12h;

DOI:10.1016/j.tetlet.2006.03.002

Reference yield:

phenyl 2,3-di-O-acetyl-4-O-chloroacetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside (888012-98-4) → Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-5-hydroxy-2-phenylsulfanyl-6-((2S,3R,4S,5R)-3,4,5-triacetoxy-tetrahydro-pyran-2-yloxymethyl)-tetrahydro-pyran-4-yl ester

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / acetonitrile / 12 h / 80 °C

2: KPF₆ / acetonitrile / 24 h / 20 °C

3: 96 percent / concd. HCl / tetrahydrofuran / 0.25 h

4: 90 percent / trimethylsilyl triflate / CH₂Cl₂ / 2 h / -40 - 0 °C

5: 95 percent / aq. sat. NaHCO₃; TBAB / diethyl ether / 0.5 h / 20 °C

With potassium hexafluorophosphate; hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; tetrabutylammomium bromide; sodium hydrogencarbonate; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1016/j.tetlet.2006.03.002

upstream raw materials:

chloroacetyl chloride

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