((1S,4R)-4-Aminocyclopent-2-en-1-yl)methanol (2S,3S)-2,3-dihydroxysuccinate

Base Information

• Chemical Name: ((1S,4R)-4-Aminocyclopent-2-en-1-yl)methanol (2S,3S)-2,3-dihydroxysuccinate
• CAS No.: 229177-52-0
• Molecular Formula: C6H11NO^.C4H6O6
• Molecular Weight: 263.25
• European Community (EC) Number: 680-296-1
• DSSTox Substance ID: DTXSID60438643
• Mol file: 229177-52-0.mol

Synonyms:229177-52-0;((1S,4R)-4-Aminocyclopent-2-en-1-yl)methanol (2S,3S)-2,3-dihydroxysuccinate;(1S-cis)-4-Amino-2-cyclopentene-1-methanol D-hydrogen tatrate;(1S,4R)-cis-4-Amino-2-cyclopentene-1-methanol D-Tartrate;((1S,4R)-4-Aminocyclopent-2-en-1-yl)methanol(2S,3S)-2,3-dihydroxysuccinate;2-Cyclopentene-1-methanol, 4-amino-, (1S,4R)-, (2S,3S)-2,3-dihydroxybutanedioate (1:1) (salt) (9CI);[(1S,4R)-4-aminocyclopent-2-en-1-yl]methanol;(2S,3S)-2,3-dihydroxybutanedioic acid;(1S-cis)-4-Amino-2-cyclopentene-1-methanol D-Tartrate;DTXSID60438643;LTSTZOJHLZNDFG-ZGMNSGLWSA-N;AMY19205;MFCD13194672;AKOS015854142;AKOS016010729;(1S,4R)-cis-4-Amino-2-cyclopentene-1-methanol (2S,3S)-2,3-Dihydroxybutanedioate;AC-27026;A878388;J-014899;(1S,4R)-4-Amino-2-cyclopentene-1-methanol D-tartrate;(1S,4R)-4-Amino-2-cyclopentene-1-methanol (2S,3S)-2,3-dihydroxybutanedioate (1:1) salt;(2S,3S)-2,3-Dihydroxybutanedioic acid--[(1S,4R)-4-aminocyclopent-2-en-1-yl]methanol (1/1)

Chemical Property of ((1S,4R)-4-Aminocyclopent-2-en-1-yl)methanol (2S,3S)-2,3-dihydroxysuccinate

Chemical Property:

• Vapor Pressure: 4.93E-08mmHg at 25°C
• Boiling Point: 399.3 °C at 760 mmHg
• Flash Point: 209.4 °C
• PSA: 161.31000
• LogP: -1.54020
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 263.10050188
• Heavy Atom Count: 18
• Complexity: 235

Purity/Quality:

99% ^*data from raw suppliers

(1S,4R)-cis-4-Amino-2-cyclopentene-1-methanolD-Tartrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C=CC1N)CO.C(C(C(=O)O)O)(C(=O)O)O
• Isomeric SMILES: C1[C@@H](C=C[C@@H]1N)CO.[C@H]([C@@H](C(=O)O)O)(C(=O)O)O
• Uses: (1S,4R)-cis-4-Amino-2-cyclopentene-1-methanol is an Abacavir intermediate; antiviral therapeutic nucleoside analog.

Technology Process of ((1S,4R)-4-Aminocyclopent-2-en-1-yl)methanol (2S,3S)-2,3-dihydroxysuccinate

There total 2 articles about ((1S,4R)-4-Aminocyclopent-2-en-1-yl)methanol (2S,3S)-2,3-dihydroxysuccinate 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: 88.0%

D-tartaric acid (147-71-7,138508-61-9) + (1S,4R)-methyl 4-aminocyclopent-2-enecarboxylate L-hydrogen tartrate (419563-22-7) → ((1S,4R)-4-aminocyclopent-2-enyl)methanol D-hydrogen tartrate (229177-52-0)

Guidance literature:

(1S,4R)-methyl 4-aminocyclopent-2-enecarboxylate L-hydrogen tartrate; With sodium tetrahydroborate; water; sodium hydroxide; at -5 - 0 ℃; for 4h;

D-tartaric acid; With sodium hydroxide; In methanol; at 65 ℃; for 0.5h; Concentration; Temperature;

Reference yield:

2-azabicyclo[2.2.1.]hept-5-en-3-one (49805-30-3) → ((1S,4R)-4-aminocyclopent-2-enyl)methanol D-hydrogen tartrate (229177-52-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: thionyl chloride / 10 - 30 °C / pH 4 - 4.5

1.2: 1 h / 20 - 65 °C

2.1: sodium hydroxide; sodium tetrahydroborate; water / 4 h / -5 - 0 °C

2.2: 0.5 h / 65 °C

With sodium tetrahydroborate; thionyl chloride; water; sodium hydroxide;

Reference yield: 88.2%

((1S,4R)-4-aminocyclopent-2-enyl)methanol D-hydrogen tartrate (229177-52-0) + N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide (171887-03-9) → (1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene (171887-04-0)

Guidance literature:

((1S,4R)-4-aminocyclopent-2-enyl)methanol D-hydrogen tartrate; With sodium carbonate; In isopropyl alcohol; at 20 ℃; for 1h;

N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide; In isopropyl alcohol; Concentration; Solvent; Reflux;

upstream raw materials:

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

D-tartaric acid

(1S,4R)-methyl 4-aminocyclopent-2-enecarboxylate L-hydrogen tartrate

Downstream raw materials:

(1R,4S)-1-[(2-amino-6-chloro-5-formamido-4-pyrimidinyl)amino]-4-(hydroxymethyl)-2-cyclopentene

Refernces