(1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethylbicyclo<3.1.0>hexane-1-carboxylic acid

Base Information

• Chemical Name: (1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethylbicyclo<3.1.0>hexane-1-carboxylic acid
• CAS No.: 190195-74-5
• Molecular Formula: C₂₂H₂₄O₄
• Molecular Weight: 352.43
• Mol file: 190195-74-5.mol

Synonyms:(1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethylbicyclo<3.1.0>hexane-1-carboxylic acid

Chemical Property of (1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethylbicyclo<3.1.0>hexane-1-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethylbicyclo<3.1.0>hexane-1-carboxylic acid

There total 5 articles about (1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethylbicyclo<3.1.0>hexane-1-carboxylic acid 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: 62.0%

(1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-1-cyanobicyclo<3.1.0>hexane (170453-00-6) → (1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethylbicyclo<3.1.0>hexane-1-carboxylic acid (190195-74-5)

Guidance literature:

With sodium hydroxide; In ethanol; for 36h; Heating;

DOI:10.1039/c39950001345

Reference yield:

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane (110567-22-1) → (1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethylbicyclo<3.1.0>hexane-1-carboxylic acid (190195-74-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 77.5 percent / LiClO₄ / acetonitrile / 96 h / 70 °C

2: 98 percent / 1,1'-thiocarbonyldiimidazole, DMAP / dimethylformamide / 1.) r.t., 3 h, 2.) 70 deg C, 30 min

3: 96.5 percent / CHCl₃; diethyl ether / 72 h / 0 °C

4: benzophenone / benzene; acetonitrile / 2 h / Irradiation

5: 25percent aq. NaOH / methanol / 24 h / Heating

With dmap; sodium hydroxide; benzophenone; lithium perchlorate; 1,1'-Thiocarbonyldiimidazole; In methanol; diethyl ether; chloroform; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1039/a604352f

Reference yield:

(3R,4S)-1-Cyano-4-benzyloxy-3-benzyloxymethylcyclopentene (170452-98-9) → (1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethylbicyclo<3.1.0>hexane-1-carboxylic acid (190195-74-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 96.5 percent / CHCl₃; diethyl ether / 72 h / 0 °C

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

3: 25percent aq. NaOH / methanol / 24 h / Heating

With sodium hydroxide; benzophenone; In methanol; diethyl ether; chloroform; acetonitrile; benzene;

DOI:10.1039/a604352f

upstream raw materials:

(1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-1-cyanobicyclo<3.1.0>hexane

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane

(3R,4S)-1-Cyano-4-benzyloxy-3-benzyloxymethylcyclopentene

(1S,2R,3R,4R)-1-Benzyloxy-2-benzyloxymethyl-4-cyano-3-hydroxycyclopentane

Downstream raw materials:

(1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-1-(2-trimethylsilylethoxyformamido)bicyclo<3.1.0>hexane

(1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-1-aminobicyclo<3.1.0>hexane

(1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-1-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)bicyclo<3.1.0>hexane

1-((1S,3S,4R,5S)-3-Benzyloxy-4-benzyloxymethyl-bicyclo[3.1.0]hex-1-yl)-1H-pyrimidine-2,4-dione