(2S,3S)-2,3-dihydroxybutanedioic acid;methyl (1R,4S)-4-aminocyclopent-2-ene-1-carboxylate

Base Information

Chemical Name:(2S,3S)-2,3-dihydroxybutanedioic acid;methyl (1R,4S)-4-aminocyclopent-2-ene-1-carboxylate
CAS No.:419563-23-8
Molecular Formula:C11H17NO8
Molecular Weight:291.258
Hs Code.:
Mol file:419563-23-8.mol

Synonyms:419563-23-8;(2S,3S)-2,3-dihydroxybutanedioic acid;methyl (1R,4S)-4-aminocyclopent-2-ene-1-carboxylate;(2S,3S)-2,3-Dihydroxysuccinic acid - methyl (1R,4S)-4-amino-2-cyclopentene-1-carboxylate (1:1);SCHEMBL7526006;DB-200508;CS-0185449;F89177;(R,4s) methyl 4-aminocyclopent-2-ene-1-carboxylate d-tartrate;Methyl (1R,4S)-4-Aminocyclopent-2-ene-1-carboxylate Tartrate;(1R,4S) Methyl 4-aminocyclopent-2-ene-1-carboxylate D-tartrate;(1R,4S)-METHYL 4-AMINOCYCLOPENT-2-ENECARBOXYLATE D-TARTRATE;(1R,4S)-Methyl 4-aminocyclopent-2-enecarboxylate (2S,3S)-2,3-dihydroxysuccinate;(2S,3S)-2,3-Dihydroxybutanedioic acid methyl (1R,4S)-4-aminocyclopent-2-ene-1-carboxylate

Suppliers and Price of (2S,3S)-2,3-dihydroxybutanedioic acid;methyl (1R,4S)-4-aminocyclopent-2-ene-1-carboxylate

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

TRC
Methyl(1R,4S)-4-Amino-2-cyclopentene-1-carboxylate(2S,3S)-2,3-DihydroxybutanedioicAcid
10g
$ 650.00

Total 3 raw suppliers

Chemical Property of (2S,3S)-2,3-dihydroxybutanedioic acid;methyl (1R,4S)-4-aminocyclopent-2-ene-1-carboxylate

Chemical Property:

PSA：167.38000
LogP:-1.35950
Hydrogen Bond Donor Count:5
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:5
Exact Mass:291.09541650
Heavy Atom Count:20
Complexity:299

Purity/Quality:

95-1289%min ^*data from raw suppliers

Methyl(1R,4S)-4-Amino-2-cyclopentene-1-carboxylate(2S,3S)-2,3-DihydroxybutanedioicAcid ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:COC(=O)C1CC(C=C1)N.C(C(C(=O)O)O)(C(=O)O)O
Isomeric SMILES:COC(=O)[C@@H]1C[C@@H](C=C1)N.[C@H]([C@@H](C(=O)O)O)(C(=O)O)O
Uses Methyl (1R,4S)-4-Amino-2-cyclopentene-1-carboxylate (2S,3S)-2,3-Dihydroxybutanedioic Acid is an intermediate used in the synthesis of ent-Abacavir (A105015), which is an enatiomer of Abacavir (A105000). Abacavir is a carbocyclic 2''-deoxyguanosine nucleoside reverse transcriptase inhibitor and an anti-HIV drug used to treat HIV infection (1). Intracellular enzymes convert Abacavir to its active form, carbovir-triphosphate (CBV-TP), which then selectively inhibits HIV reverse transcriptase by incorporating into viral DNA (2). Abacavir is metabolized in the liver by uridine diphosphate glucuronyltransferase and alcohol dehydrogenase resulting in inactive glucuronide and carboxylate metabolites, respectively.

Technology Process of (2S,3S)-2,3-dihydroxybutanedioic acid;methyl (1R,4S)-4-aminocyclopent-2-ene-1-carboxylate

There total 3 articles about (2S,3S)-2,3-dihydroxybutanedioic acid;methyl (1R,4S)-4-aminocyclopent-2-ene-1-carboxylate 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: 91.0%

: 419563-23-8,419563-22-7
(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester tartrate

Guidance literature:

Reference yield:

: 67-56-1
methanol

: 147-71-7,138508-61-9
D-tartaric acid

: 49805-30-3
racemic 2-azabicyclo[2.2.1]hept-5-en-3-one

: 419563-23-8,419563-22-7
(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester tartrate

Guidance literature:: methanol; racemic 2-azabicyclo[2.2.1]hept-5-en-3-one; With thionyl chloride; at 0 - 20 ℃; for 1h;

D-tartaric acid; With triethylamine; In water; at 20 - 50 ℃; for 2h; pH=1.8 - 2;

Reference yield:

: 67-56-1
methanol

: 147-71-7,138508-61-9
D-tartaric acid

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 419563-23-8,419563-22-7
(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester tartrate

Guidance literature:: methanol; 2-azabicyclo[2.2.1.]hept-5-en-3-one; With hydrogenchloride; In water; at 5 ℃; for 1h;

With L-Tartaric acid; triethylamine; In water; at 20 ℃; for 18h;

D-tartaric acid; With triethylamine; In water; for 18h; Temperature; Time;