[(S)-1-((4R,5R)-2-Oxo-5-phenethyl-2λ⁴-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(S)-1-((4R,5R)-2-Oxo-5-phenethyl-2λ⁴-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester
• CAS No.: 1053389-37-9
• Molecular Formula: C₂₆H₂₇NO₅S
• Molecular Weight: 465.57

Synonyms:[(S)-1-((4R,5R)-2-Oxo-5-phenethyl-2λ⁴-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester

Chemical Property of [(S)-1-((4R,5R)-2-Oxo-5-phenethyl-2λ⁴-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester

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Technology Process of [(S)-1-((4R,5R)-2-Oxo-5-phenethyl-2λ⁴-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester

There total 1 articles about [(S)-1-((4R,5R)-2-Oxo-5-phenethyl-2λ⁴-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid benzyl 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:

(2S,3R,4R)-2--1,6-diphenylhexane-3,4-diol (154659-14-0) → [(S)-1-((4R,5R)-2-Oxo-5-phenethyl-2λ4-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester (1053389-37-9)

Guidance literature:

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

DOI:10.1021/jo961060j

Reference yield:

[(S)-1-((4R,5R)-2-Oxo-5-phenethyl-2λ4-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester (1053389-37-9) → [(S)-1-((4R,5R)-2,2-Dioxo-5-phenethyl-2λ6-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester (182204-80-4)

Guidance literature:

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; at 0 ℃; for 1h; Yield given;

DOI:10.1021/jo961060j

Reference yield:

[(S)-1-((4R,5R)-2-Oxo-5-phenethyl-2λ4-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester (1053389-37-9) → (4S,5S)-4-Benzyl-5-((R)-1-hydroxy-3-phenyl-propyl)-oxazolidin-2-one

Guidance literature:

Multi-step reaction with 2 steps

1: RuCl₃*3H₂O, NaIO₄ / CCl₄; acetonitrile; H₂O / 1 h / 0 °C

2: 1.) H₂, Et₃N, 2.) aq. H₂SO₄ / 1.) Pd/C / 1) THF, 50 psi, 18 h; 2) THF, 25 deg C, 30 min

With ruthenium trichloride; sodium periodate; sulfuric acid; hydrogen; triethylamine; palladium on activated charcoal; In tetrachloromethane; water; acetonitrile;

DOI:10.1021/jo961060j

upstream raw materials:

(2S,3R,4R)-2--1,6-diphenylhexane-3,4-diol

Downstream raw materials:

[(S)-1-((4R,5R)-2,2-Dioxo-5-phenethyl-2λ⁶-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester

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