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

Base Information

• Chemical Name: (2S,5S,6R)-6-Benzyloxymethyl-2-oxo-2-phenoxy-5,6-dihydro-2H-2λ⁵-[1,2]oxaphosphinin-5-ol
• CAS No.: 863012-00-4
• Molecular Formula: C₁₈H₁₉O₅P
• Molecular Weight: 346.32

Synonyms:(2S,5S,6R)-6-Benzyloxymethyl-2-oxo-2-phenoxy-5,6-dihydro-2H-2λ⁵-[1,2]oxaphosphinin-5-ol

Chemical Property of (2S,5S,6R)-6-Benzyloxymethyl-2-oxo-2-phenoxy-5,6-dihydro-2H-2λ⁵-[1,2]oxaphosphinin-5-ol

Chemical Property:

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Technology Process of (2S,5S,6R)-6-Benzyloxymethyl-2-oxo-2-phenoxy-5,6-dihydro-2H-2λ⁵-[1,2]oxaphosphinin-5-ol

There total 4 articles about (2S,5S,6R)-6-Benzyloxymethyl-2-oxo-2-phenoxy-5,6-dihydro-2H-2λ⁵-[1,2]oxaphosphinin-5-ol 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%

(3aS,4R,6S,7aR)-4-Benzyloxymethyl-6-oxo-6-phenoxy-tetrahydro-6λ5-[1,3]dioxolo[4,5-d][1,2]oxaphosphinin-2-one (863012-18-4) → (2S,5S,6R)-6-Benzyloxymethyl-2-oxo-2-phenoxy-5,6-dihydro-2H-2λ5-[1,2]oxaphosphinin-5-ol (863012-00-4)

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -50 - 0 ℃; for 2.5h;

DOI:10.1021/jo0505122

Reference yield:

(2S,6S)-6-Benzyloxymethyl-2-phenoxy-3,6-dihydro-[1,2]oxaphosphinine 2-oxide (863011-98-7) → (2S,5S,6R)-6-Benzyloxymethyl-2-oxo-2-phenoxy-5,6-dihydro-2H-2λ5-[1,2]oxaphosphinin-5-ol (863012-00-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / m-CPBA; N-methylmorpholine; citric acid / OsO₄ / acetone; 2-methyl-propan-2-ol; H₂O / 48 h

2: 95 percent / Et₃N / CH₂Cl₂ / 3 h / -40 - 10 °C

3: 74 percent / KHMDS / tetrahydrofuran; toluene / 2.5 h / -50 - 0 °C

With 4-methyl-morpholine; potassium hexamethylsilazane; triethylamine; 3-chloro-benzenecarboperoxoic acid; citric acid; osmium(VIII) oxide; In tetrahydrofuran; dichloromethane; water; acetone; toluene; tert-butyl alcohol;

DOI:10.1021/jo0505122

Reference yield:

Allyl-phosphonic acid (S)-1-benzyloxymethyl-allyl ester phenyl ester → (2S,5S,6R)-6-Benzyloxymethyl-2-oxo-2-phenoxy-5,6-dihydro-2H-2λ5-[1,2]oxaphosphinin-5-ol (863012-00-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / Heating

2: 84 percent / m-CPBA; N-methylmorpholine; citric acid / OsO₄ / acetone; 2-methyl-propan-2-ol; H₂O / 48 h

3: 95 percent / Et₃N / CH₂Cl₂ / 3 h / -40 - 10 °C

4: 74 percent / KHMDS / tetrahydrofuran; toluene / 2.5 h / -50 - 0 °C

With 4-methyl-morpholine; potassium hexamethylsilazane; triethylamine; 3-chloro-benzenecarboperoxoic acid; citric acid; osmium(VIII) oxide; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; water; acetone; toluene; tert-butyl alcohol;

DOI:10.1021/jo0505122

upstream raw materials:

(3aS,4R,6S,7aR)-4-Benzyloxymethyl-6-oxo-6-phenoxy-tetrahydro-6λ⁵-[1,3]dioxolo[4,5-d][1,2]oxaphosphinin-2-one

(2S,6S)-6-Benzyloxymethyl-2-phenoxy-3,6-dihydro-[1,2]oxaphosphinine 2-oxide

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

Downstream raw materials:

(3aR,5S,7R,7aS)-7-Benzyloxymethyl-5-phenoxy-2-trichloromethyl-3a,4,7,7a-tetrahydro-1,6-dioxa-3-aza-5-phospha-indene 5-oxide

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