(1R,4R,5S,6R)-4-Amino-2-oxabicyclo[3.1.0]hexane-4,6-dicarboxylic acid

Base Information

• Chemical Name: (1R,4R,5S,6R)-4-Amino-2-oxabicyclo[3.1.0]hexane-4,6-dicarboxylic acid
• CAS No.: 191471-52-0
• Molecular Formula: C7H9NO5
• Molecular Weight: 187.15000
• UNII: S96JF4J697
• DSSTox Substance ID: DTXSID90436637
• Wikipedia: LY-379,268
• Wikidata: Q6460430
• Pharos Ligand ID: V5B4T6AQVJP2
• ChEMBL ID: CHEMBL275079
• Mol file: 191471-52-0.mol

Synonyms:2-oxa-4-aminobicyclo(3.1.0)hexane-4,6-dicarboxylic acid;LY 379268;LY-379268;LY379268

Chemical Property of (1R,4R,5S,6R)-4-Amino-2-oxabicyclo[3.1.0]hexane-4,6-dicarboxylic acid

Chemical Property:

• PSA: 109.85000
• LogP: -0.80180
• Storage Temp.: Store at +4°C
• Solubility.: Soluble in H2O or NaOH
• XLogP3: -4.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 187.04807239
• Heavy Atom Count: 13
• Complexity: 291

Purity/Quality:

98% ^*data from raw suppliers

LY379268 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C2C(C2O1)C(=O)O)(C(=O)O)N
• Isomeric SMILES: C1[C@]([C@@H]2[C@H]([C@@H]2O1)C(=O)O)(C(=O)O)N
• Uses: LY 379268 is a group II metabotropic glutamate receptors (mGlu2/3) receptor agonist (1,2). Studies have shown that LY379268 significantly attenuated cocaine-induced increases in DA in nonhuman primates.

Technology Process of (1R,4R,5S,6R)-4-Amino-2-oxabicyclo[3.1.0]hexane-4,6-dicarboxylic acid

There total 6 articles about (1R,4R,5S,6R)-4-Amino-2-oxabicyclo[3.1.0]hexane-4,6-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%

(+)-4-(spiro-5'-hydantoin)-2-oxabicyclo<3.1.0>hexane-6-carboxylic acid (191471-66-6) → (+)-4-amino-2-oxabicyclo<3.1.0>hexane-4,6-dicarboxylic acid (191471-52-0)

Guidance literature:

With sodium hydroxide; Heating;

DOI:10.1021/jm980616n

Reference yield:

(+/-)-ethyl 2-oxabicyclo<3.1.0>hex-3-ene-6-carboxylate (128300-08-3) → (+)-4-amino-2-oxabicyclo<3.1.0>hexane-4,6-dicarboxylic acid (191471-52-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) thexylborane, 2.) 30 percent H₂O₂, phosphate buffer pH 7 / 1.) THF, 0-5 deg C, 2 h, 2.) THF, RT, 14 h

2: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -67 deg C, 5 min, 2.) CH₂Cl₂, -50 deg C, 15 min

3: 79 percent / methanol / 23 h / Ambient temperature

4: 93 percent / 2 N NaOH / 0.5 h / Ambient temperature

5: 79 percent / 2 N NaOH / Heating

With sodium hydroxide; oxalyl dichloride; phosphate buffer pH 7; thexylborane; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; In methanol;

DOI:10.1021/jm980616n

Reference yield:

(+/-)-ethyl 4-hydroxy-2-oxabicyclo<3.1.0>hexane-6-carboxylate → (+)-4-amino-2-oxabicyclo<3.1.0>hexane-4,6-dicarboxylic acid (191471-52-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -67 deg C, 5 min, 2.) CH₂Cl₂, -50 deg C, 15 min

2: 79 percent / methanol / 23 h / Ambient temperature

3: 93 percent / 2 N NaOH / 0.5 h / Ambient temperature

4: 79 percent / 2 N NaOH / Heating

With sodium hydroxide; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In methanol;

DOI:10.1021/jm980616n

upstream raw materials:

(+)-4-(spiro-5'-hydantoin)-2-oxabicyclo<3.1.0>hexane-6-carboxylic acid

(+/-)-ethyl 2-oxabicyclo<3.1.0>hex-3-ene-6-carboxylate