(2S,3R,4S)-CCG

Base Information

• Chemical Name: (2S,3R,4S)-CCG
• CAS No.: 117857-95-1
• Molecular Formula: C₆H₉NO₄
• Molecular Weight: 159.142
• Hs Code.: 2922500090
• DSSTox Substance ID: DTXSID00415498
• Nikkaji Number: J343.938K
• Wikidata: Q82224448
• Metabolomics Workbench ID: 130023
• ChEMBL ID: CHEMBL282842
• Mol file: 117857-95-1.mol

Synonyms:Cyclopropaneaceticacid, a-amino-2-carboxy-, [1S-[1a(R*),2a]]-; L-CCG III

Chemical Property of (2S,3R,4S)-CCG

Chemical Property:

• PSA: 100.62000
• LogP: -0.18070
• Storage Temp.: Store at RT
• Solubility.: H2O: soluble
• XLogP3: -3.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 159.05315777
• Heavy Atom Count: 11
• Complexity: 203

Purity/Quality:

98.5% ^*data from raw suppliers

L-CCG-lll ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C1C(=O)O)C(C(=O)O)N
• Isomeric SMILES: C1[C@H]([C@H]1C(=O)O)[C@@H](C(=O)O)N
• Uses: L-CCG-IV is a potent small molecule agonist at the NMDA receptor.

Technology Process of (2S,3R,4S)-CCG

There total 111 articles about (2S,3R,4S)-CCG 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: 93.0%

C-[(R)-C-Furan-2-yl-C-((1S,2S)-2-furan-2-yl-cyclopropyl)]-methylamine (206192-93-0) → (2R,3R,4R) α-(Carboxycyclopropyl)glycine (22255-17-0,95673-12-4,104758-69-2,104758-70-5,117857-93-9,117857-94-0,117857-95-1,117857-96-2,125412-10-4,125412-11-5,125412-12-6,125412-13-7,129446-08-8,499982-30-8)

Guidance literature:

With ozone; In methanol; at -78 ℃; for 0.5h;

DOI:10.1016/S0957-4166(98)00061-5

Reference yield: 93.0%

C-[(S)-C-Furan-2-yl-C-((1R,2R)-2-furan-2-yl-cyclopropyl)]-methylamine (206192-91-8) → α-(carboxycyclopropyl)-glycine (22255-17-0,95673-12-4,104758-69-2,104758-70-5,117857-93-9,117857-94-0,117857-95-1,117857-96-2,125412-10-4,125412-11-5,125412-12-6,125412-13-7,129446-08-8,499982-30-8)

Guidance literature:

With ozone; In methanol; at -78 ℃; for 0.5h;

DOI:10.1016/S0957-4166(98)00061-5

Reference yield: 93.0%

N-Cbz-(O-Me)-trans-2-(carboxycyclopropyl)glycine OBO ester (255057-20-6) → (2S,3S,4R)-α-(carboxycyclopropyl)glycine (117857-95-1,499982-30-8)

Guidance literature:

With hydrogenchloride; at 90 ℃; for 5h;

DOI:10.1021/jo991066j

upstream raw materials:

2-((R)-Benzyloxycarbonylamino-methoxycarbonyl-methyl)-cyclopropanecarboxylic acid ethyl ester

(1R,2S)-2-((S)-1-tert-Butoxycarbonylamino-2-hydroxy-ethyl)-cyclopropanecarboxylic acid ethyl ester

(1R,2S)-2-((S)-tert-Butoxycarbonylamino-carboxy-methyl)-cyclopropanecarboxylic acid

N-Cbz-(O-Me)-trans-2-(carboxycyclopropyl)glycine OBO ester

Downstream raw materials:

(R)-4-(2-Carboxy-cyclopropyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

(2R,3R,4R) α-(Carboxycyclopropyl)glycine

(2R,3S,4S) α-(Carboxycyclopropyl)glycine

(R)-4-[(R)-2-((R)-2-Hydroxy-1-phenyl-ethylcarbamoyl)-cyclopropyl]-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

Refernces

• 1、 Wallock, Nathaniel J,Donaldson, William A. "Synthesis of cyclopropanes via organoiron methodology: Stereoselective preparation of cis-2-(2′-carboxycyclopropyl)glycine". . p. 4541 - 4543. Retrieved 2002.
• 2、 Wallock, Nathaniel J.,Donaldson, William A.. "Reactivity of (Bicyclo[5.1.0]octadienyl)iron(1+) Cations: Application to the Synthesis of cis-2-(2′-Carboxycyclopropyl)glycines". . p. 2997 - 3007. Retrieved 2007/10/03.