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

Base Information

• Chemical Name: (2S,5R,6R)-2-Benzyloxy-2-oxo-6-trityloxymethyl-5,6-dihydro-2H-2λ⁵-[1,2]oxaphosphinin-5-ol
• CAS No.: 863012-15-1
• Molecular Formula: C₃₁H₂₉O₅P
• Molecular Weight: 512.542

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

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

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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

There total 8 articles about (2S,5R,6R)-2-Benzyloxy-2-oxo-6-trityloxymethyl-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: 75.0%

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) → (2S,5R,6R)-2-Benzyloxy-2-oxo-6-trityloxymethyl-5,6-dihydro-2H-2λ5-[1,2]oxaphosphinin-5-ol (863012-15-1)

Guidance literature:

With methanol; magnesium methanolate; 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) → (2S,5R,6R)-2-Benzyloxy-2-oxo-6-trityloxymethyl-5,6-dihydro-2H-2λ5-[1,2]oxaphosphinin-5-ol (863012-15-1)

Guidance literature:

Multi-step reaction with 4 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

4: 75 percent / MeOH; Mg(OMe)2 / 20 °C

With methanol; N-methyl-2-indolinone; 18-crown-6 ether; magnesium methanolate; 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 → (2S,5R,6R)-2-Benzyloxy-2-oxo-6-trityloxymethyl-5,6-dihydro-2H-2λ5-[1,2]oxaphosphinin-5-ol (863012-15-1)

Guidance literature:

Multi-step reaction with 6 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

6: 75 percent / MeOH; Mg(OMe)2 / 20 °C

With methanol; n-butyllithium; N-methyl-2-indolinone; 18-crown-6 ether; magnesium methanolate; 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:

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

(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

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

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