phenyl 2-deoxy-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside S-oxide

Base Information

• Chemical Name: phenyl 2-deoxy-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside S-oxide
• CAS No.: 935268-63-6
• Molecular Formula: C₄₀H₄₁Cl₄NO₇SSi
• Molecular Weight: 849.732

Synonyms:phenyl 2-deoxy-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside S-oxide

Chemical Property of phenyl 2-deoxy-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside S-oxide

Chemical Property:

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Technology Process of phenyl 2-deoxy-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside S-oxide

There total 5 articles about phenyl 2-deoxy-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside S-oxide 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: 93.0%

phenyl 2-deoxy-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside (935268-62-5) → phenyl 2-deoxy-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside S-oxide (935268-63-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 - -60 ℃; for 2h;

DOI:10.1021/ja069060g

Reference yield:

phenyl 2-deoxy-3,6-di-O-benzyl-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside (935268-61-4) → phenyl 2-deoxy-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside S-oxide (935268-63-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 20 °C

2: 93 percent / mCPBA / CH₂Cl₂ / 2 h / -78 - -60 °C

With 2,6-dimethylpyridine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/ja069060g

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → phenyl 2-deoxy-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside S-oxide (935268-63-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / 2,6-lutidine / CH₂Cl₂ / 20 °C

2: 93 percent / mCPBA / CH₂Cl₂ / 2 h / -78 - -60 °C

With 2,6-dimethylpyridine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/ja069060g

upstream raw materials:

phenyl 2-deoxy-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside

phenyl 2-deoxy-3,6-di-O-benzyl-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside

t-butyldimethylsiyl triflate

benzyl bromide

Downstream raw materials:

phenyl 2-deoxy-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-tetrachlorophthalimido-β-D-glucopyranosyl-(1->4)-2-deoxy-6-O-benzyl-2-tetrachlorophthalimido-1-thio-β-D-glucopyranoside S-oxide

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