(1S,4R)-1-((benzyloxy)methyl)-4-hydroxycyclopent-2-enecarbonitrile

Base Information

• Chemical Name: (1S,4R)-1-((benzyloxy)methyl)-4-hydroxycyclopent-2-enecarbonitrile
• CAS No.: 815587-21-4
• Molecular Formula: C₁₄H₁₅NO₂
• Molecular Weight: 229.279
• Mol file: 815587-21-4.mol

Synonyms:(1S,4R)-1-((benzyloxy)methyl)-4-hydroxycyclopent-2-enecarbonitrile

Chemical Property of (1S,4R)-1-((benzyloxy)methyl)-4-hydroxycyclopent-2-enecarbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4R)-1-((benzyloxy)methyl)-4-hydroxycyclopent-2-enecarbonitrile

There total 2 articles about (1S,4R)-1-((benzyloxy)methyl)-4-hydroxycyclopent-2-enecarbonitrile 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:

(S)-1-((benzyloxy)methyl)-4-oxocyclopent-2-enecarbonitrile (815587-18-9) → (1S,4S)-1-((benzyloxy)methyl)-4-hydroxycyclopent-2-enecarbonitrile (815587-22-5) + (1S,4R)-1-((benzyloxy)methyl)-4-hydroxycyclopent-2-enecarbonitrile (815587-21-4)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 ℃; for 0.333333h;

DOI:10.1021/jo040215h

Reference yield:

(4R,5S)-3-((1R,2S)-2-((benzyloxy)methyl)-2-methyl-4-oxocyclopentyl)-4,5-diphenyloxazolidin-2-one (815587-12-3) → (1S,4R)-1-((benzyloxy)methyl)-4-hydroxycyclopent-2-enecarbonitrile (815587-21-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0 °C

2: NaBH₄; CeCl₃*7H₂O / methanol / 0.33 h / 0 °C

With sodium tetrahydroborate; cerium(III) chloride; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol;

DOI:10.1021/jo040215h

Reference yield: 91.0%

(1S,4R)-1-((benzyloxy)methyl)-4-hydroxycyclopent-2-enecarbonitrile (815587-21-4) + chloroformic acid ethyl ester (541-41-3) → (1R,4S)-4-((benzyloxy)methyl)-4-cyanocyclopent-2-enyl ethyl carbonate (815587-24-7)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1021/jo040215h

upstream raw materials:

(S)-1-((benzyloxy)methyl)-4-oxocyclopent-2-enecarbonitrile

(4R,5S)-3-((1R,2S)-2-((benzyloxy)methyl)-2-methyl-4-oxocyclopentyl)-4,5-diphenyloxazolidin-2-one

Downstream raw materials:

(1R,4S)-4-((benzyloxy)methyl)-4-cyanocyclopent-2-enyl ethyl carbonate

(1S,4R)-1-((benzyloxy)methyl)-4-(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)cyclopent-2-enecarbonitrile