(R_S)-S-phenyl 2,3-di-O-p-bromobenzyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside S-oxide

Base Information

• Chemical Name: (R_S)-S-phenyl 2,3-di-O-p-bromobenzyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside S-oxide
• CAS No.: 407616-86-8
• Molecular Formula: C₃₃H₃₀Br₂O₆S
• Molecular Weight: 714.472

Synonyms:(R_S)-S-phenyl 2,3-di-O-p-bromobenzyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside S-oxide

Chemical Property of (R_S)-S-phenyl 2,3-di-O-p-bromobenzyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside S-oxide

Chemical Property:

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Technology Process of (R_S)-S-phenyl 2,3-di-O-p-bromobenzyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside S-oxide

There total 3 articles about (R_S)-S-phenyl 2,3-di-O-p-bromobenzyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside 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: 84.0%

S-phenyl 2,3-di-O-p-bromobenzyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside (407616-83-5) → (RS)-S-phenyl 2,3-di-O-p-bromobenzyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside S-oxide (407616-86-8)

Guidance literature:

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

DOI:10.1016/S0040-4020(01)01087-0

Reference yield:

1-bromomethyl-4-bromobenzene (589-15-1) → (RS)-S-phenyl 2,3-di-O-p-bromobenzyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside S-oxide (407616-86-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / NaH / dimethylformamide / 3 h / 20 °C

2: 84 percent / MCPBA / CH₂Cl₂ / 3 h / -78 °C

With sodium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)01087-0

Reference yield:

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-19-9) → (RS)-S-phenyl 2,3-di-O-p-bromobenzyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside S-oxide (407616-86-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / NaH / dimethylformamide / 3 h / 20 °C

2: 84 percent / MCPBA / CH₂Cl₂ / 3 h / -78 °C

With sodium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)01087-0

upstream raw materials:

S-phenyl 2,3-di-O-p-bromobenzyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside

1-bromomethyl-4-bromobenzene

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Downstream raw materials:

1-O-(4,6-di-O-acetyl-2,3-di-O-dodecanoyl-β-D-mannopyranosyl)-4-O-tert-butyldiphenylsilyl-erythritol

4-tert-butyldiphenylsiloxy-2Z-buten-1-yl 4,6-di-O-acetyl-2,3-di-O-dodecanoyl-β-D-mannopyranoside

4-tert-butyldiphenylsiloxy-2Z-buten-1-yl 4,6-O-benzylidene-2,3-di-O-dodecanoyl-β-D-mannopyranoside

4-tert-butyldiphenylsiloxy-2Z-buten-1-yl 2,3-di-O-dodecanoyl-β-D-mannopyranoside

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