[R,(-)]-3-Hydroxy-4-pentenoic acid

Base Information

• Chemical Name: [R,(-)]-3-Hydroxy-4-pentenoic acid
• CAS No.: 38996-04-2
• Molecular Formula: C5H8O3
• Molecular Weight: 116.11500
• Mol file: 38996-04-2.mol

Synonyms:(R)-(-)-3-Hydroxy-penten-(4)-saeure;(R)-3-hydroxy-4-pentenoic acid;(R)-3-hydroxypent-4-enoic acid;

Chemical Property of [R,(-)]-3-Hydroxy-4-pentenoic acid

Chemical Property:

• PSA: 57.53000
• LogP: 0.00800

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of [R,(-)]-3-Hydroxy-4-pentenoic acid

There total 7 articles about [R,(-)]-3-Hydroxy-4-pentenoic 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: 83.0%

N-[(2R,3S)-2-bromo-3-hydroxy-4-pentenoyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.01,5]decane (291523-42-7) → (R)-3-hydroxy-4-pentenoic acid (38996-04-2)

Guidance literature:

N-[(2R,3S)-2-bromo-3-hydroxy-4-pentenoyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.0^1,5]decane; With water; triethylamine; In dichloromethane; at 0 ℃; for 0.5h;

With aluminium amalgam; In dichloromethane; at 0 ℃; for 0.166667h; Further stages.;

DOI:10.1021/jo000124u

Reference yield: 81.0%

(3R)-3-(methoxymethoxy)pent-4-enoic acid (1233533-11-3) → (R)-3-hydroxy-4-pentenoic acid (38996-04-2)

Guidance literature:

With methanol; toluene-4-sulfonic acid; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1055/s-0029-1218694

Reference yield:

(RS)-3-hydroxypent-4-enenitrile (27451-36-1) → (2S)-1-cyano-2-hydroxy-3-butene (6071-81-4) + (R)-3-hydroxy-4-pentenenitrile (6071-81-4,27451-36-1,7451-85-6) + (S)-3-hydroxy-4-pentenoic acid (38996-05-3) + (R)-3-hydroxy-4-pentenoic acid (38996-04-2)

Guidance literature:

With Rhodococcus erythropolis SET₁ cells; In aq. phosphate buffer; at 25 ℃; for 48h; pH=7; enantioselective reaction; Microbiological reaction;

DOI:10.1002/ejoc.201403201

upstream raw materials:

ethyl 3-hydroxypent-4-enoate

N-[(2R,3S)-2-bromo-3-hydroxy-4-pentenoyl]-(1S,5R,7R)-10,10-dimethyl-3-thioxo-2-aza-4-oxatricyclo[6.2.1.0^1,5]decane

(3R)-3-(methoxymethoxy)pent-4-enoic acid

(RS)-3-hydroxypent-4-enenitrile

Refernces

• 1、 Sabitha, Gowravaram,Reddy, S. Siva Sankara,Bhaskar, Vangala,Yadav, Jhillu S.. "A concise synthesis of (-)-(3 S,6 R)-3,6-Dihydroxy-10-methylundecanoic acid using a cross-metathesis approach". experimental part. p. 1217 - 1222. Retrieved 2010/06/14.
• 2、 Graef, Silke,Braun, Manfred. "De-novo Synthesis of Enantiomerically Pure Deoxy- and Aminodeoxyfuranosides". . p. 1091 - 1098. Retrieved 2007/10/02.