(R)-(-)-2-hydroxy-3-(E)-pentenenitrile

Base Information

• Chemical Name: (R)-(-)-2-hydroxy-3-(E)-pentenenitrile
• CAS No.: 124439-85-6
• Molecular Formula: C₅H₇NO
• Molecular Weight: 97.1167
• Mol file: 124439-85-6.mol

Synonyms:

Chemical Property of (R)-(-)-2-hydroxy-3-(E)-pentenenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-(-)-2-hydroxy-3-(E)-pentenenitrile

There total 10 articles about (R)-(-)-2-hydroxy-3-(E)-pentenenitrile 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: 72.0%

trans-Crotonaldehyde (123-73-9,4170-30-3) + potassium cyanide (151-50-8) → (R)-(-)-2-hydroxy-3-(E)-pentenenitrile (6812-26-6,10017-08-0,116908-78-2,118710-58-0,124439-85-6)

Guidance literature:

potassium cyanide; With hydrogenchloride; pH=1; cooling;

trans-Crotonaldehyde; With defatted almond meal oxynitrilase; In di-isopropyl ether; at 2 ℃; for 12h;

DOI:10.1016/j.tetasy.2005.03.018

Reference yield: 70.0%

trans-Crotonaldehyde (123-73-9,4170-30-3) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → (R)-(-)-2-hydroxy-3-(E)-pentenenitrile (6812-26-6,10017-08-0,116908-78-2,118710-58-0,124439-85-6)

Guidance literature:

With Prunus mume (R)-hydroxynitrile lyase; Na-citrate buffer; In di-isopropyl ether; at 25 ℃; for 14h; pH=4.0;

DOI:10.1016/j.tetasy.2006.02.003

Reference yield:

trans-Crotonaldehyde (123-73-9,4170-30-3) + trimethylsilyl cyanide (7677-24-9) → (R)-(-)-2-hydroxy-3-(E)-pentenenitrile (6812-26-6,10017-08-0,116908-78-2,118710-58-0,124439-85-6) + (E)-(S)-(+)-2-hydroxypent-3-enenitrile (160865-93-0)

Guidance literature:

With (S)-2--3-methyl-1-butanol titanium tetraisopropoxide; In dichloromethane; at -80 ℃; for 36h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00058a037

upstream raw materials:

trans-Crotonaldehyde

hydrogen cyanide

trimethylsilyl cyanide

potassium cyanide

Downstream raw materials:

(R,E)-N-((S)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine

tert-butyl (S)-1-(benzyloxy)but-3-en-2-yl((R,E)-2-(tert-butyldiphenylsilyloxy)pent-3-enyl)carbamate

(R,E)-N-((R)-1-(benzyloxy)but-3-en-2-yl)-2-(tert-butyldiphenylsilyloxy)pent-3-en-1-amine

tert-butyl (R)-1-(benzyloxy)but-3-en-2-yl((R,E)-2-(tert-butyldiphenylsilyloxy)pent-3-enyl)carbamate