(2R,3S,4R)-2,3-Epoxy-4,5-isopropylidenedioxy-1-phenylpentan-1-one

Base Information

• Chemical Name: (2R,3S,4R)-2,3-Epoxy-4,5-isopropylidenedioxy-1-phenylpentan-1-one
• CAS No.: 222626-17-7
• Molecular Formula: C₁₄H₁₆O₄
• Molecular Weight: 248.279
• Mol file: 222626-17-7.mol

Synonyms:(2R,3S,4R)-2,3-Epoxy-4,5-isopropylidenedioxy-1-phenylpentan-1-one

Chemical Property of (2R,3S,4R)-2,3-Epoxy-4,5-isopropylidenedioxy-1-phenylpentan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R)-2,3-Epoxy-4,5-isopropylidenedioxy-1-phenylpentan-1-one

There total 4 articles about (2R,3S,4R)-2,3-Epoxy-4,5-isopropylidenedioxy-1-phenylpentan-1-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:

(E)-1-C-phenyl-2,3-dideoxy-4,5-O-isopropylidene-D-glycero-pent-2-enose (222626-15-5) → (2S,3R,4R)-2,3-Epoxy-4,5-isopropylidenedioxy-1-phenylpentan-1-one + (2R,3S,4R)-2,3-Epoxy-4,5-isopropylidenedioxy-1-phenylpentan-1-one (222626-17-7)

Guidance literature:

With immobilised poly-D-leucine; dihydrogen peroxide; sodium carbonate; In 1,2-dimethoxyethane; water; at -3 - 0 ℃; for 24h; Yield given; Yields of byproduct given;

DOI:10.1016/S0040-4039(98)02689-6

Reference yield:

(Z)-1-C-phenyl-2,3-dideoxy-4,5-O-isopropylidene-D-glycero-pent-2-enose (222626-16-6) → (2S,3R,4R)-2,3-Epoxy-4,5-isopropylidenedioxy-1-phenylpentan-1-one + (2R,3S,4R)-2,3-Epoxy-4,5-isopropylidenedioxy-1-phenylpentan-1-one (222626-17-7)

Guidance literature:

With immobilised poly-D-leucine; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; for 0.583333h; Yield given; Yields of byproduct given;

DOI:10.1016/S0040-4039(98)02689-6

Reference yield:

(Benzoylmethylene)triphenylphosphorane (20913-05-7,859-65-4) → (2R,3S,4R)-2,3-Epoxy-4,5-isopropylidenedioxy-1-phenylpentan-1-one (222626-17-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: SiO₂-NaIO₄ / CH₂Cl₂

1.2: CH₂Cl₂ / 2 h

2.1: Na₂CO₃*1.5H₂O₂; poly-D-leucine / 1,2-dimethoxy-ethane; H₂O / 0.5 h / 20 °C

With sodium periodate; poly-D-leucine; dihydrogen peroxide; silica gel; sodium carbonate; In 1,2-dimethoxyethane; dichloromethane; water; 1.2: Wittig reaction / 2.1: Julia-Colonna epoxidation;

DOI:10.1039/b007100p

upstream raw materials:

(Z)-1-C-phenyl-2,3-dideoxy-4,5-O-isopropylidene-D-glycero-pent-2-enose

(E)-1-C-phenyl-2,3-dideoxy-4,5-O-isopropylidene-D-glycero-pent-2-enose

(Benzoylmethylene)triphenylphosphorane

1,2:5,6-di-O-isopropylidene-D-mannitol

Downstream raw materials:

(1S,2S,3S,4R)-2,3-Epoxy-4,5-isopropylidenedioxy-1-phenylpentan-1-ol

(1S,2R,3S,4R)-2,3-Epoxy-4,5-isopropylidenedioxy-1-phenyl-1-[(N-phenyl)carbamoyloxy]pentane