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

Base Information

• Chemical Name: Benzoic acid (2S,5R,6R)-2-benzyloxy-2-oxo-6-trityloxymethyl-5,6-dihydro-2H-2λ⁵-[1,2]oxaphosphinin-5-yl ester
• CAS No.: 863012-14-0
• Molecular Formula: C₃₈H₃₃O₆P
• Molecular Weight: 616.65

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

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

Chemical Property:

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

There total 7 articles about Benzoic acid (2S,5R,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: 74.0%

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) + Potassium benzoate (582-25-2) → Benzoic acid (2S,5R,6R)-2-benzyloxy-2-oxo-6-trityloxymethyl-5,6-dihydro-2H-2λ5-[1,2]oxaphosphinin-5-yl ester (863012-14-0)

Guidance literature:

With 18-crown-6 ether; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jo0505122

Reference yield:

(2S,6S)-2-Benzyloxy-6-trityloxymethyl-3,6-dihydro-[1,2]oxaphosphinine 2-oxide (863012-09-3) → Benzoic acid (2S,5R,6R)-2-benzyloxy-2-oxo-6-trityloxymethyl-5,6-dihydro-2H-2λ5-[1,2]oxaphosphinin-5-yl ester (863012-14-0)

Guidance literature:

Multi-step reaction with 3 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

3: 74 percent / 18-crown-6 / dimethylformamide / 20 °C

With N-methyl-2-indolinone; 18-crown-6 ether; triethylamine; citric acid; dmap; osmium(VIII) oxide; In dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

DOI:10.1021/jo0505122

Reference yield:

Allyl-phosphonic acid phenyl ester (S)-1-trityloxymethyl-allyl ester → Benzoic acid (2S,5R,6R)-2-benzyloxy-2-oxo-6-trityloxymethyl-5,6-dihydro-2H-2λ5-[1,2]oxaphosphinin-5-yl ester (863012-14-0)

Guidance literature:

Multi-step reaction with 5 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

5: 74 percent / 18-crown-6 / dimethylformamide / 20 °C

With n-butyllithium; N-methyl-2-indolinone; 18-crown-6 ether; triethylamine; citric acid; dmap; osmium(VIII) oxide; Grubbs catalyst first generation; In 1,2-dimethoxyethane; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

DOI:10.1021/jo0505122

upstream raw materials:

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

Potassium benzoate

(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:

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

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