(1R,4S,5S)-4-Benzoyloxymethyl-3-oxabicyclo<3.1.0>hexan-2-one

Base Information

• Chemical Name: (1R,4S,5S)-4-Benzoyloxymethyl-3-oxabicyclo<3.1.0>hexan-2-one
• CAS No.: 131267-39-5
• Molecular Formula: C₁₃H₁₂O₄
• Molecular Weight: 232.236
• Mol file: 131267-39-5.mol

Synonyms:(1R,4S,5S)-4-Benzoyloxymethyl-3-oxabicyclo<3.1.0>hexan-2-one

Chemical Property of (1R,4S,5S)-4-Benzoyloxymethyl-3-oxabicyclo<3.1.0>hexan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S,5S)-4-Benzoyloxymethyl-3-oxabicyclo<3.1.0>hexan-2-one

There total 4 articles about (1R,4S,5S)-4-Benzoyloxymethyl-3-oxabicyclo<3.1.0>hexan-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: 94.0%

(1R,4S,5S)-4-Benzoyloxymethyl-3-oxa-7,8-diazabicyclo<3.3.0>oct-7-en-2-one (131267-38-4) → (1R,4S,5S)-4-Benzoyloxymethyl-3-oxabicyclo<3.1.0>hexan-2-one (131267-39-5)

Guidance literature:

With benzophenone; In acetonitrile; benzene; for 2h; Irradiation;

DOI:10.1016/0008-6215(90)80130-U

Reference yield:

(5S)-5-(hydroxymethyl)-5H-furan-2-one (78508-96-0) → (1R,4S,5S)-4-Benzoyloxymethyl-3-oxabicyclo<3.1.0>hexan-2-one (131267-39-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

2: 88 percent / CHCl₃; diethyl ether / 18 h / 0 °C

3: 94 percent / benzophenone / benzene; acetonitrile / 2 h / Irradiation

With pyridine; benzophenone; In diethyl ether; dichloromethane; chloroform; acetonitrile; benzene;

DOI:10.1016/0008-6215(90)80130-U

Reference yield:

(5S)-5-(benzoyloxymethyl)-5H-furan-2-one (96086-02-1) → (1R,4S,5S)-4-Benzoyloxymethyl-3-oxabicyclo<3.1.0>hexan-2-one (131267-39-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / CHCl₃; diethyl ether / 18 h / 0 °C

2: 94 percent / benzophenone / benzene; acetonitrile / 2 h / Irradiation

With benzophenone; In diethyl ether; chloroform; acetonitrile; benzene;

DOI:10.1016/0008-6215(90)80130-U

upstream raw materials:

(1R,4S,5S)-4-Benzoyloxymethyl-3-oxa-7,8-diazabicyclo<3.3.0>oct-7-en-2-one

(5S)-5-(hydroxymethyl)-5H-furan-2-one

(5S)-5-(benzoyloxymethyl)-5H-furan-2-one

benzoyl chloride

Downstream raw materials:

1-O-Acetyl-5-O-benzoyl-2,3-dideoxy-2,3-methano-β-D-ribofuranose

Benzoic acid (1S,2S,5R)-4-(4-amino-2-oxo-2H-pyrimidin-1-yl)-3-oxa-bicyclo[3.1.0]hex-2-ylmethyl ester

2',3'-Dideoxy-2',3'-α-methano-α-cytidine