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

Base Information

• Chemical Name: (R_S)-S-phenyl 2,3-di-O-allyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside S-oxide
• CAS No.: 407616-84-6
• Molecular Formula: C₂₅H₂₈O₆S
• Molecular Weight: 456.56

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

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

There total 2 articles about (R_S)-S-phenyl 2,3-di-O-allyl-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: 90.0%

S-phenyl 2,3-di-O-allyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside (407616-82-4) → (RS)-S-phenyl 2,3-di-O-allyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside S-oxide (407616-84-6)

Guidance literature:

With MMPP; In tetrahydrofuran; water; at 0 ℃;

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-allyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside S-oxide (407616-84-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / NaH / dimethylformamide / 3 h / 20 °C

2: 90 percent / MMPP / tetrahydrofuran; H₂O / 0 °C

With sodium hydride; In tetrahydrofuran; water; N,N-dimethyl-formamide;

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

Reference yield: 80.0%

2,4-O-ethylidene-3-O-tert-butyldimethylsilyl-D-erythritol (407616-81-3) + (RS)-S-phenyl 2,3-di-O-allyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside S-oxide (407616-84-6) → 1-O-(2,3-di-O-allyl-4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol (407616-87-9)

Guidance literature:

(R_S)-S-phenyl 2,3-di-O-allyl-4,6-O-benzylidene-1-thia-α-D-mannopyranoside S-oxide; With trifluoromethylsulfonic anhydride; 3 A molecular sieve; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -75 ℃; for 0.25h;

2,4-O-ethylidene-3-O-tert-butyldimethylsilyl-D-erythritol; In dichloromethane; at -70 ℃; for 1h;

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

upstream raw materials:

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

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

Downstream raw materials:

1-O-(2,3-di-O-allyl-4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol

1-O-(4,6-O-benzylidene-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol

1-O-(4,6-O-benzylidene-2,3-di-O-dodecanoyl-β-D-mannopyranosyl)-3-O-tert-butyldimethylsilyl-2,4-O-ethylidene-D-erythritol

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