(4S,5R,6S)-3,4,5,6-tetrahydro-4-benzyl-5-hydroxy-6-(2-methylpropyl)-2H-1,3-oxazin-2-one

Base Information

• Chemical Name: (4S,5R,6S)-3,4,5,6-tetrahydro-4-benzyl-5-hydroxy-6-(2-methylpropyl)-2H-1,3-oxazin-2-one
• CAS No.: 182204-90-6
• Molecular Formula: C₁₅H₂₁NO₃
• Molecular Weight: 263.337

Synonyms:(4S,5R,6S)-3,4,5,6-tetrahydro-4-benzyl-5-hydroxy-6-(2-methylpropyl)-2H-1,3-oxazin-2-one

Chemical Property of (4S,5R,6S)-3,4,5,6-tetrahydro-4-benzyl-5-hydroxy-6-(2-methylpropyl)-2H-1,3-oxazin-2-one

Chemical Property:

Purity/Quality:

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Technology Process of (4S,5R,6S)-3,4,5,6-tetrahydro-4-benzyl-5-hydroxy-6-(2-methylpropyl)-2H-1,3-oxazin-2-one

There total 4 articles about (4S,5R,6S)-3,4,5,6-tetrahydro-4-benzyl-5-hydroxy-6-(2-methylpropyl)-2H-1,3-oxazin-2-one 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: 12.0%

[(S)-1-((4R,5R)-5-Isobutyl-2,2-dioxo-2λ6-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester (182204-79-1) → N-(phenylmethyl)acetamide (588-46-5) + (4S,5S)-4-benzyl-5-((1R)-1-hydroxy-3-methylbutyl)-1,3-oxazolidin-2-one (182204-86-0) + (4S,5R,6S)-3,4,5,6-tetrahydro-4-benzyl-5-hydroxy-6-(2-methylpropyl)-2H-1,3-oxazin-2-one (182204-90-6)

Guidance literature:

In acetonitrile; for 4.5h; Heating;

DOI:10.1021/jo961060j

Reference yield:

(2S,3R,4R)-2--6-methyl-1-phenylheptane-3,4-diol (154659-11-7) → (4S,5R,6S)-3,4,5,6-tetrahydro-4-benzyl-5-hydroxy-6-(2-methylpropyl)-2H-1,3-oxazin-2-one (182204-90-6)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 67 percent / acetonitrile / 4.5 h / Heating

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-oxo-2λ4-[1,3,2]dioxathiolan-4-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester (1053616-37-7) → (4S,5R,6S)-3,4,5,6-tetrahydro-4-benzyl-5-hydroxy-6-(2-methylpropyl)-2H-1,3-oxazin-2-one (182204-90-6)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 67 percent / acetonitrile / 4.5 h / Heating

With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile;

DOI:10.1021/jo961060j

upstream raw materials:

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

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

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

Downstream raw materials:

(2S,3R,4S)-2-Amino-6-methyl-1-phenyl-heptane-3,4-diol

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