(R)-2-(((Benzyloxy)carbonyl)amino)-2-cyclohexylacetic acid

Base Information

• Chemical Name: (R)-2-(((Benzyloxy)carbonyl)amino)-2-cyclohexylacetic acid
• CAS No.: 69901-85-5
• Molecular Formula: C16H21NO4
• Molecular Weight: 291.347
• Hs Code.: 2924299090
• DSSTox Substance ID: DTXSID50561116
• Nikkaji Number: J2.210.428D
• Wikidata: Q72502134
• Mol file: 69901-85-5.mol

Synonyms:Z-D-Chg-OH;69901-85-5;(R)-2-(((Benzyloxy)carbonyl)amino)-2-cyclohexylacetic acid;Cbz-D-cyclohexyl glycine;(2R)-2-cyclohexyl-2-(phenylmethoxycarbonylamino)acetic acid;Z-cyclohexyl-D-Gly-OH;N-Z-D-|A-Cyclohexylglycine;MFCD00191082;SCHEMBL433978;(R)-2-(benzyloxycarbonylamino)-2-cyclohexylacetic acid;DTXSID50561116;CUSYTUPJAYLNFQ-CQSZACIVSA-N;BCP13869;CS-B1518;AKOS015888883;AC-24035;DS-18393;HY-77635;Z-D-Chg-OH, >=98.0% (TLC);F14548;(R)-benzyloxycarbonylamino-cyclohexyl-acetic acid;EN300-7390051;(2R)-{[(Benzyloxy)carbonyl]amino}(cyclohexyl)acetic acid;(2R)-2-{[(benzyloxy)carbonyl]amino}-2-cyclohexylacetic acid

Chemical Property of (R)-2-(((Benzyloxy)carbonyl)amino)-2-cyclohexylacetic acid

Chemical Property:

• Melting Point: 103℃
• Boiling Point: 492.1 °C at 760 mmHg
• PKA: 3.99±0.10(Predicted)
• Flash Point: 251.4 °C
• PSA: 79.12000
• Density: 1.2 g/cm³
• LogP: 3.15070
• Storage Temp.: 2-8°C
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 291.14705815
• Heavy Atom Count: 21
• Complexity: 346

Purity/Quality:

98%,99%, ^*data from raw suppliers

Z-D-2-cyclohexylglycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)C(C(=O)O)NC(=O)OCC2=CC=CC=C2
• Isomeric SMILES: C1CCC(CC1)[C@H](C(=O)O)NC(=O)OCC2=CC=CC=C2

Technology Process of (R)-2-(((Benzyloxy)carbonyl)amino)-2-cyclohexylacetic acid

There total 7 articles about (R)-2-(((Benzyloxy)carbonyl)amino)-2-cyclohexylacetic 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:

N-(benzyloxycarbonyl)-α-dehydrocyclohexylglycine → (S)-[[(benzyloxy)carbonyl]amino](cyclohexyl)acetic acid (69901-75-3) + (R)-N-benzyloxycarbonylcyclohexylglicine (69901-85-5)

Guidance literature:

With (R)-(-)-[(S)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; hydrogen; triethylamine; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; In ethanol; 1,2-dichloro-ethane; at 25 ℃; for 24h; under 4654.33 Torr; Title compound not separated from byproducts;

DOI:10.1021/ol050869s

Reference yield:

O-benzyl carbamate (621-84-1) → (R)-N-benzyloxycarbonylcyclohexylglicine (69901-85-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 43 percent / methanesulfonic acid / toluene / 2 h / Heating

2: H₂; (R)-(S)-1-Ph₃P-2-(CHMeP(t-Bu)2)ferrocene; Et₃N / [(p-cymene)RuCl₂]2 / ethanol; 1,2-dichloro-ethane / 24 h / 25 °C / 4654.33 Torr

With methanesulfonic acid; (R)-(-)-[(S)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; hydrogen; triethylamine; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; In ethanol; 1,2-dichloro-ethane; toluene;

DOI:10.1021/ol050869s

Reference yield:

2-cyclohexyl-2-oxoethanoic acid (4354-49-8) → (R)-N-benzyloxycarbonylcyclohexylglicine (69901-85-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 43 percent / methanesulfonic acid / toluene / 2 h / Heating

2: H₂; (R)-(S)-1-Ph₃P-2-(CHMeP(t-Bu)2)ferrocene; Et₃N / [(p-cymene)RuCl₂]2 / ethanol; 1,2-dichloro-ethane / 24 h / 25 °C / 4654.33 Torr

With methanesulfonic acid; (R)-(-)-[(S)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine; hydrogen; triethylamine; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; In ethanol; 1,2-dichloro-ethane; toluene;

DOI:10.1021/ol050869s

upstream raw materials:

(R)-(-)-methyl N-benzyloxycarbonylamino-2-cyclohexylethanoate

O-benzyl carbamate

2-cyclohexyl-2-oxoethanoic acid

(R)-Phenylglycine methyl ester

Downstream raw materials:

{(R)-Cyclohexyl-[(R)-2-cyclohexyl-2-(trityl-amino)-ethylcarbamoyl]-methyl}-carbamic acid benzyl ester

(R)-4-Cyclohexyl-5-oxo-oxazolidine-3-carboxylic acid benzyl ester

3R,7R-dicyclohexyl-1,4,6-triazabicyclo<3.3.0.>oct-4-ene

(R)-N²-((R)-2-Amino-2-cyclohexyl-ethyl)-1-cyclohexyl-N¹-trityl-ethane-1,2-diamine

Refernces

• 1、 Corey, E. J.,Ohtani, Mitsuaki. "ENANTIOSPECIFIC SYNTHESIS OF A RIGID, C2 SYMMETRIC, CHIRAL GUANIDINE BY A NEW AND DIRECT METHOD". . p. 5227 - 5230. Retrieved 2007/10/02.