(1R,3R,5S,6R)-2-Amino-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid

Base Information

• Chemical Name: (1R,3R,5S,6R)-2-Amino-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid
• CAS No.: 234085-22-4
• Molecular Formula: C₈H₁₀FNO₄
• Molecular Weight: 203.17
• DSSTox Substance ID: DTXSID20443394
• Wikidata: Q82261174
• Mol file: 234085-22-4.mol

Synonyms:234085-22-4;(1R,2R,3R,5S,6R)-2-amino-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid;SCHEMBL7212206;DTXSID20443394;(1R,3R,5S,6R)-2-Amino-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid;Bicyclo[3.1.0]hexane-2,6-dicarboxylic acid,2-amino-3-fluoro-,(1R,2R,3R,5S,6R)-(9ci)

Chemical Property of (1R,3R,5S,6R)-2-Amino-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid

Chemical Property:

• PSA: 100.62000
• LogP: 0.15740
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 203.05938596
• Heavy Atom Count: 14
• Complexity: 321

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(C2C(C1F)(C(=O)O)N)C(=O)O
• Isomeric SMILES: C1[C@@H]2[C@H]([C@@H]2[C@]([C@@H]1F)(C(=O)O)N)C(=O)O

Technology Process of (1R,3R,5S,6R)-2-Amino-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid

There total 21 articles about (1R,3R,5S,6R)-2-Amino-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic 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: 79.0%

ethyl (1S,2S,3S,5R,6S)-2-spiro-5'-hydantoin-3-fluorobicyclo[3.1.0]hexane-6-carboxylate (278176-04-8) → (1S, 2S, 3S, 5R, 6S)-2-amino-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (234085-19-9,234085-17-7,234085-14-4,234085-22-4,234085-20-2)

Guidance literature:

With 60percent aq. H₂SO₄; at 140 ℃; for 48h;

DOI:10.1021/jm000346k

Reference yield: 74.0%

ethyl (1S,2S,3S,5R,6S)-2-spiro-5'-hydantoin-3-fluorobicyclo[3.1.0]hexane-6-carboxylic acid (234085-33-7) → (1S, 2S, 3S, 5R, 6S)-2-amino-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (234085-19-9,234085-17-7,234085-14-4,234085-22-4,234085-20-2)

Guidance literature:

With sulfuric acid; at 145 ℃; for 84h;

DOI:10.1248/cpb.55.37

Reference yield: 73.0%

ethyl (1R,2R,3R,5S,6R)-2-spiro-5'-hydantoin-3-fluorobicyclo[3.1.0]hexane-6-carboxylic acid (234085-35-9) → (1R,2R,3R,5S,6R)-2-amino-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (234085-19-9,234085-14-4,234085-22-4,234085-20-2)

Guidance literature:

With 60percent aq. H₂SO₄; at 140 ℃; for 48h;

DOI:10.1021/jm000346k

upstream raw materials:

ethyl (1R,2R,3R,5S,6R)-2-spiro-5'-hydantoin-3-fluorobicyclo[3.1.0]hexane-6-carboxylic acid

(+/-)-(1S,5R,6S)-ethyl 2-oxobicyclo[3.1.0]hexane-6-carboxylate

ethyl (1S,2S,3S,5R,6S)-2-spiro-5'-hydantoin-3-fluorobicyclo[3.1.0]hexane-6-carboxylic acid

ethyl (1S,2S,3S,5R,6S)-2-spiro-5'-hydantoin-3-fluorobicyclo[3.1.0]hexane-6-carboxylate