Methanesulfonic acid (2S,5S,6R)-2-benzyloxy-2-oxo-6-trityloxymethyl-5,6-dihydro-2H-2λ⁵-[1,2]oxaphosphinin-5-yl ester

Base Information

• Chemical Name: Methanesulfonic acid (2S,5S,6R)-2-benzyloxy-2-oxo-6-trityloxymethyl-5,6-dihydro-2H-2λ⁵-[1,2]oxaphosphinin-5-yl ester
• CAS No.: 863012-13-9
• Molecular Formula: C₃₂H₃₁O₇PS
• Molecular Weight: 590.634

Synonyms:Methanesulfonic acid (2S,5S,6R)-2-benzyloxy-2-oxo-6-trityloxymethyl-5,6-dihydro-2H-2λ⁵-[1,2]oxaphosphinin-5-yl ester

Chemical Property of Methanesulfonic acid (2S,5S,6R)-2-benzyloxy-2-oxo-6-trityloxymethyl-5,6-dihydro-2H-2λ⁵-[1,2]oxaphosphinin-5-yl ester

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Technology Process of Methanesulfonic acid (2S,5S,6R)-2-benzyloxy-2-oxo-6-trityloxymethyl-5,6-dihydro-2H-2λ⁵-[1,2]oxaphosphinin-5-yl ester

There total 6 articles about Methanesulfonic acid (2S,5S,6R)-2-benzyloxy-2-oxo-6-trityloxymethyl-5,6-dihydro-2H-2λ⁵-[1,2]oxaphosphinin-5-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: 60.0%

(2S,4R,5S,6R)-2-phenylmethoxy-6-[(triphenylmethoxy)methyl]-1,2-oxaphosphorinane-4,5-diol 2-oxide (863012-08-2) + methanesulfonyl chloride (124-63-0) → Methanesulfonic acid (2S,5S,6R)-2-benzyloxy-2-oxo-6-trityloxymethyl-5,6-dihydro-2H-2λ5-[1,2]oxaphosphinin-5-yl ester (863012-13-9)

Guidance literature:

With triethylamine; dmap; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/jo0505122

Reference yield:

(2S,6S)-2-Benzyloxy-6-trityloxymethyl-3,6-dihydro-[1,2]oxaphosphinine 2-oxide (863012-09-3) → Methanesulfonic acid (2S,5S,6R)-2-benzyloxy-2-oxo-6-trityloxymethyl-5,6-dihydro-2H-2λ5-[1,2]oxaphosphinin-5-yl ester (863012-13-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / NMO; citric acid / OsO₄ / acetone; 2-methyl-propan-2-ol; H₂O / 48 h

2: 60 percent / Et₃N / DMAP / CH₂Cl₂ / 0 - 20 °C

With N-methyl-2-indolinone; triethylamine; citric acid; dmap; osmium(VIII) oxide; In dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1021/jo0505122

Reference yield:

Allyl-phosphonic acid phenyl ester (S)-1-trityloxymethyl-allyl ester → Methanesulfonic acid (2S,5S,6R)-2-benzyloxy-2-oxo-6-trityloxymethyl-5,6-dihydro-2H-2λ5-[1,2]oxaphosphinin-5-yl ester (863012-13-9)

Guidance literature:

Multi-step reaction with 4 steps

1: BuLi / 1,2-dimethoxy-ethane; hexane / -50 - 20 °C

2: 98 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 6 h / Heating

3: 81 percent / NMO; citric acid / OsO₄ / acetone; 2-methyl-propan-2-ol; H₂O / 48 h

4: 60 percent / Et₃N / DMAP / CH₂Cl₂ / 0 - 20 °C

With n-butyllithium; N-methyl-2-indolinone; triethylamine; citric acid; dmap; osmium(VIII) oxide; Grubbs catalyst first generation; In 1,2-dimethoxyethane; hexane; dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1021/jo0505122

upstream raw materials:

(2S,4R,5S,6R)-2-phenylmethoxy-6-[(triphenylmethoxy)methyl]-1,2-oxaphosphorinane-4,5-diol 2-oxide

methanesulfonyl chloride

(2S,6S)-2-Benzyloxy-6-trityloxymethyl-3,6-dihydro-[1,2]oxaphosphinine 2-oxide

(S)-Allyl-phosphonic acid benzyl ester (S)-1-trityloxymethyl-allyl ester

Downstream raw materials:

Benzoic acid (2S,5R,6R)-2-benzyloxy-2-oxo-6-trityloxymethyl-5,6-dihydro-2H-2λ⁵-[1,2]oxaphosphinin-5-yl ester

(2S,5R,6R)-2-Benzyloxy-2-oxo-6-trityloxymethyl-5,6-dihydro-2H-2λ⁵-[1,2]oxaphosphinin-5-ol

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