(-)-(1S,4R)-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID

Base Information

• Chemical Name: (-)-(1S,4R)-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID
• CAS No.: 102579-71-5
• Molecular Formula: C₆H₉NO₂
• Molecular Weight: 127.143
• Mol file: 102579-71-5.mol

Synonyms:2-Cyclopentene-1-carboxylicacid, 4-amino-, trans-(?à)-; 2-Cyclopentene-1-carboxylic acid, 4-amino-, trans-

Chemical Property of (-)-(1S,4R)-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID

Chemical Property:

• PSA: 63.32000
• LogP: 0.67470
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

trans-4-Aminocyclopent-2-enecarboxylicacid 95+% ^*data from reagent suppliers

Safty Information:

• Statements: 43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (-)-(1S,4R)-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID

There total 25 articles about (-)-(1S,4R)-4-AMINOCYCLOPENT-2-ENECARBOXYLIC 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: 83.7%

(1S,4R)-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester tartrate (419563-22-7) → (-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid (102579-71-5,102579-72-6,102679-78-7,134003-04-6,134234-04-1)

Guidance literature:

With methanol; water; triethylamine; lithium hydroxide; at -20 ℃; pH=6 - 7;

Reference yield: 49.0%

racemic N-hydroxymethyl vince lactam → (-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid (102579-71-5,102579-72-6,102679-78-7,134003-04-6,134234-04-1) + (1S,4R)-N-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one (157810-20-3)

Guidance literature:

With water; benzylamine; lipase B from Candida antarctica; In isopropyl alcohol; at 60 ℃; for 2h; Enzymatic reaction;

DOI:10.1016/j.tetasy.2016.06.019

Reference yield: 46.0%

racemic 2-azabicyclo[2.2.1]hept-5-en-3-one (49805-30-3) → (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one (130931-83-8) + (-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid (102579-71-5,102579-72-6,102679-78-7,134003-04-6,134234-04-1)

Guidance literature:

With lipase B from Candida antarctica; In water; isopropyl alcohol; at 60 ℃; for 4h; stereospecific reaction; Enzymatic reaction;

DOI:10.1002/ejoc.200800723

upstream raw materials:

3-tosyl-2-azabicyclo [2.2.1]hepta-2,5-diene

2-azabicyclo[2.2.1.]hept-5-en-3-one

cyclopenta-1,3-diene

racemic 2-azabicyclo[2.2.1]hept-5-en-3-one

Downstream raw materials:

(cis)-methyl 4-aminocyclopent-2-enecarboxylate

(1S,3R)-1-(9-adenenyl)-3-(N-hydroxycarbamoyl)cyclopentane

PMC6

(1S,3R)-3-Benzyloxymethyl-cyclopentylamine