Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester
• CAS No.: 864776-76-1
• Molecular Formula: C₄₄H₄₇ClO₆SSi
• Molecular Weight: 767.458

Synonyms:Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester

Chemical Property of Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester

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Technology Process of Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester

There total 3 articles about Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester 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%

(2R,3S,4S,5S,6R)-3,5-Bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-ol + Chloroacetic anhydride (541-88-8) → Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester (864776-76-1)

Guidance literature:

With pyridine; at 20 ℃; for 1h;

DOI:10.1002/anie.200500777

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester (864776-76-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N; DMAP / dimethylformamide / 12 h / 20 °C

2: 93 percent / pyridine / 1 h / 20 °C

With pyridine; dmap; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1002/anie.200500777

Reference yield:

phenyl 2,4-di-O-benzyl-1-phenylthio-α-D-mannopyranoside (210295-06-0) → Chloro-acetic acid (2R,3R,4S,5S,6R)-3,5-bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-phenylsulfanyl-tetrahydro-pyran-4-yl ester (864776-76-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N; DMAP / dimethylformamide / 12 h / 20 °C

2: 93 percent / pyridine / 1 h / 20 °C

With pyridine; dmap; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1002/anie.200500777

upstream raw materials:

Chloroacetic anhydride

tert-butylchlorodiphenylsilane

phenyl 2,4-di-O-benzyl-1-phenylthio-α-D-mannopyranoside

Downstream raw materials:

Chloro-acetic acid (2R,3R,4S,5S,6S)-3,5-bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-(4-hydroxy-3-nitro-benzyloxy)-tetrahydro-pyran-4-yl ester

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