[(S)-1-((4R,5R)-5-Isobutyl-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

Base Information

• Chemical Name: [(S)-1-((4R,5R)-5-Isobutyl-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester
• CAS No.: 182204-97-3
• Molecular Formula: C₁₉H₂₉NO₆S
• Molecular Weight: 399.508

Synonyms:[(S)-1-((4R,5R)-5-Isobutyl-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

Chemical Property of [(S)-1-((4R,5R)-5-Isobutyl-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

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Useful:

Technology Process of [(S)-1-((4R,5R)-5-Isobutyl-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

There total 2 articles about [(S)-1-((4R,5R)-5-Isobutyl-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl 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:

[(S)-1-((4R,5R)-5-Isobutyl-2-oxo-2λ4-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester → [(S)-1-((4R,5R)-5-Isobutyl-2,2-dioxo-2λ6-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester (182204-97-3)

Guidance literature:

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

DOI:10.1021/jo961060j

Reference yield:

(2S,3R,4R)-2--6-methyl-1-phenylheptane-3,4-diol (154799-20-9) → [(S)-1-((4R,5R)-5-Isobutyl-2,2-dioxo-2λ6-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester (182204-97-3)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride, Et₃N / CH₂Cl₂ / 0.08 h / 0 °C

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

With ruthenium trichloride; sodium periodate; thionyl chloride; triethylamine; In tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1021/jo961060j

Reference yield:

[(S)-1-((4R,5R)-5-Isobutyl-2,2-dioxo-2λ6-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester (182204-97-3) → (4S,5S)-4-cyclohexylmethyl-5-<(1'R)-1'-hydroxy-3-methylbutyl>oxazolidin-2-one

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-lutidine / CH₂Cl₂ / 0.33 h

2: 1.) tetra-n-butylammonium fluoride, 2.) aq. H₂SO₄ / 1) THF, 0 deg C, 1 h; 2) THF, rt, 30 min

3: H₂ / Rh/Al₂O₃ / 2585.7 Torr

With 2,6-dimethylpyridine; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; Rh/Al₂O₃; In dichloromethane;

DOI:10.1021/jo961060j

upstream raw materials:

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

Downstream raw materials:

C₂₁H₃₅NO₆SSi

(4S,5S)-4-benzyl-5-((1R)-1-hydroxy-3-methylbutyl)-1,3-oxazolidin-2-one

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