(2S,4R,5S,6R)-2-Oxo-2-phenoxy-6-trityloxymethyl-2λ⁵-[1,2]oxaphosphinane-4,5-diol

Base Information

• Chemical Name: (2S,4R,5S,6R)-2-Oxo-2-phenoxy-6-trityloxymethyl-2λ⁵-[1,2]oxaphosphinane-4,5-diol
• CAS No.: 375373-54-9
• Molecular Formula: C₃₀H₂₉O₆P
• Molecular Weight: 516.53

Synonyms:(2S,4R,5S,6R)-2-Oxo-2-phenoxy-6-trityloxymethyl-2λ⁵-[1,2]oxaphosphinane-4,5-diol

Chemical Property of (2S,4R,5S,6R)-2-Oxo-2-phenoxy-6-trityloxymethyl-2λ⁵-[1,2]oxaphosphinane-4,5-diol

Chemical Property:

Purity/Quality:

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Technology Process of (2S,4R,5S,6R)-2-Oxo-2-phenoxy-6-trityloxymethyl-2λ⁵-[1,2]oxaphosphinane-4,5-diol

There total 4 articles about (2S,4R,5S,6R)-2-Oxo-2-phenoxy-6-trityloxymethyl-2λ⁵-[1,2]oxaphosphinane-4,5-diol 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: 69.6%

(2S,6S)-2-Phenoxy-6-trityloxymethyl-3,6-dihydro-[1,2]oxaphosphinine 2-oxide (375373-53-8) → (2S,4R,5S,6R)-2-Oxo-2-phenoxy-6-trityloxymethyl-2λ5-[1,2]oxaphosphinane-4,5-diol (375373-54-9)

Guidance literature:

With osmium(VIII) oxide; N-methyl-2-indolinone; citric acid; In acetone; tert-butyl alcohol; for 24h;

DOI:10.1021/ol016491p

Reference yield:

diphenyl allylphosphonate (101111-39-1) → (2S,4R,5S,6R)-2-Oxo-2-phenoxy-6-trityloxymethyl-2λ5-[1,2]oxaphosphinane-4,5-diol (375373-54-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 56.6 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / -78 °C

2: 97.4 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 5 h / Heating

3: 69.6 percent / aq. OsO₄; NMO; citric acid / acetone; 2-methyl-propan-2-ol / 24 h

With osmium(VIII) oxide; N-methyl-2-indolinone; citric acid; Grubbs catalyst first generation; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; acetone; tert-butyl alcohol;

DOI:10.1021/ol016491p

Reference yield:

(S)-Allyl-phosphonic acid phenyl ester (S)-1-trityloxymethyl-allyl ester (375373-52-7) → (2S,4R,5S,6R)-2-Oxo-2-phenoxy-6-trityloxymethyl-2λ5-[1,2]oxaphosphinane-4,5-diol (375373-54-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 97.4 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 5 h / Heating

2: 69.6 percent / aq. OsO₄; NMO; citric acid / acetone; 2-methyl-propan-2-ol / 24 h

With osmium(VIII) oxide; N-methyl-2-indolinone; citric acid; Grubbs catalyst first generation; In dichloromethane; acetone; tert-butyl alcohol;

DOI:10.1021/ol016491p

upstream raw materials:

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

diphenyl allylphosphonate

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

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