((4S,5S)-5-Benzyl-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-yl)-phosphonic acid dimethyl ester

Base Information

• Chemical Name: ((4S,5S)-5-Benzyl-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-yl)-phosphonic acid dimethyl ester
• CAS No.: 1026523-54-5
• Molecular Formula: C₁₁H₁₅O₆PS
• Molecular Weight: 306.276

Synonyms:((4S,5S)-5-Benzyl-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-yl)-phosphonic acid dimethyl ester

Chemical Property of ((4S,5S)-5-Benzyl-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-yl)-phosphonic acid dimethyl ester

Chemical Property:

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Technology Process of ((4S,5S)-5-Benzyl-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-yl)-phosphonic acid dimethyl ester

There total 3 articles about ((4S,5S)-5-Benzyl-2-oxo-2λ⁴-[1,3,2]dioxathiolan-4-yl)-phosphonic acid dimethyl 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:

Dimethyl (1(S),2(S)-dihydroxy-3-phenylpropyl)phosphonate (160423-15-4) → ((4S,5S)-5-Benzyl-2-oxo-2λ4-[1,3,2]dioxathiolan-4-yl)-phosphonic acid dimethyl ester (1026523-54-5)

Guidance literature:

With thionyl chloride; triethylamine; In dichloromethane; at 0 ℃; for 0.0833333h;

DOI:10.1021/jo00104a064

Reference yield:

(2S)-2-benzyloxy-3-phenylpropanal (118535-75-4) → ((4S,5S)-5-Benzyl-2-oxo-2λ4-[1,3,2]dioxathiolan-4-yl)-phosphonic acid dimethyl ester (1026523-54-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / TiCl₄ / CH₂Cl₂ / 1.5 h / -78 °C

2: 70 percent / H₂ / Pd(OH)2 / methanol / 12 h / Ambient temperature

3: SOCl₂, Et₃N / CH₂Cl₂ / 0.08 h / 0 °C

With thionyl chloride; hydrogen; titanium tetrachloride; triethylamine; palladium dihydroxide; In methanol; dichloromethane;

DOI:10.1021/jo00104a064

Reference yield:

((1S,2S)-2-Benzyloxy-1-hydroxy-3-phenyl-propyl)-phosphonic acid dimethyl ester (160423-10-9) → ((4S,5S)-5-Benzyl-2-oxo-2λ4-[1,3,2]dioxathiolan-4-yl)-phosphonic acid dimethyl ester (1026523-54-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / H₂ / Pd(OH)2 / methanol / 12 h / Ambient temperature

2: SOCl₂, Et₃N / CH₂Cl₂ / 0.08 h / 0 °C

With thionyl chloride; hydrogen; triethylamine; palladium dihydroxide; In methanol; dichloromethane;

DOI:10.1021/jo00104a064

upstream raw materials:

Dimethyl (1(S),2(S)-dihydroxy-3-phenylpropyl)phosphonate

(2S)-2-benzyloxy-3-phenylpropanal

((1S,2S)-2-Benzyloxy-1-hydroxy-3-phenyl-propyl)-phosphonic acid dimethyl ester

Downstream raw materials:

((4S,5S)-5-Benzyl-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-phosphonic acid dimethyl ester

((1S,2R)-2-Azido-1-hydroxy-3-phenyl-propyl)-phosphonic acid dimethyl ester

((1R,2S)-1-Azido-2-hydroxy-3-phenyl-propyl)-phosphonic acid dimethyl ester

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