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

Base Information

• Chemical Name: (1S,2R,3R,4R)-1-Benzyloxy-2-benzyloxymethyl-4-cyano-3-hydroxycyclopentane
• CAS No.: 160860-62-8
• Molecular Formula: C₂₁H₂₃NO₃
• Molecular Weight: 337.419
• Mol file: 160860-62-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (1S,2R,3R,4R)-1-Benzyloxy-2-benzyloxymethyl-4-cyano-3-hydroxycyclopentane 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: 77.5%

(2R,3S)-benzyloxy-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexane (110567-22-1) + potassium cyanide (151-50-8) → (1S,2R,3R,4R)-1-Benzyloxy-2-benzyloxymethyl-4-cyano-3-hydroxycyclopentane (160860-62-8)

Guidance literature:

With lithium perchlorate; In acetonitrile; at 70 ℃; for 96h;

DOI:10.1039/a604352f

Reference yield: 98.0%

(1S,2R,3R,4R)-1-Benzyloxy-2-benzyloxymethyl-4-cyano-3-hydroxycyclopentane (160860-62-8) → (3R,4S)-1-Cyano-4-benzyloxy-3-benzyloxymethylcyclopentene (170452-98-9)

Guidance literature:

With dmap; 1,1'-Thiocarbonyldiimidazole; In N,N-dimethyl-formamide; 1.) r.t., 3 h, 2.) 70 deg C, 30 min;

DOI:10.1039/a604352f

Reference yield:

(1S,2R,3R,4R)-1-Benzyloxy-2-benzyloxymethyl-4-cyano-3-hydroxycyclopentane (160860-62-8) → 4-Amino-1-((1S,3S,4R,5S)-3-benzyloxy-4-benzyloxymethyl-bicyclo[3.1.0]hex-1-yl)-1H-pyrimidin-2-one (190195-81-4)

Guidance literature:

Multi-step reaction with 11 steps

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

2: 96.5 percent / CHCl₃; diethyl ether / 72 h / 0 °C

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

4: 25percent aq. NaOH / methanol / 24 h / Heating

5: Et₃N, DPPA / toluene / 1.) r.t., 2 h, 2.) 80 deg C, 2 h

6: toluene / 1.) 80 deg C, 2 h, 2.) r.t., overnight

7: 99 percent / Bu₄NF / acetonitrile; tetrahydrofuran / 4 h / 70 °C

8: CH₂Cl₂ / Ambient temperature

9: 2 M HCl / ethanol / Heating

10: POCl₃, Et₃N / acetonitrile / 2 h / Ambient temperature

11: conc. NH₄OH / dioxane / 48 h / 40 °C

With hydrogenchloride; dmap; ammonium hydroxide; sodium hydroxide; benzophenone; diphenyl-phosphinic acid; tetrabutyl ammonium fluoride; triethylamine; 1,1'-Thiocarbonyldiimidazole; trichlorophosphate; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1039/a604352f

upstream raw materials:

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

potassium cyanide

Downstream raw materials:

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

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

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

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