Boc-D-Chg-OH

Base Information

• Chemical Name: Boc-D-Chg-OH
• CAS No.: 70491-05-3
• Molecular Formula: C13H23 N O4
• Molecular Weight: 257.33
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID40426700
• Nikkaji Number: J2.095.787E
• Wikidata: Q72449036
• Mol file: 70491-05-3.mol

Synonyms:70491-05-3;Boc-D-Chg-OH;Boc-D-cyclohexylglycine;(R)-2-((tert-Butoxycarbonyl)amino)-2-cyclohexylacetic acid;N-Boc-2-Cyclohexyl-D-glycine;MFCD00133629;(2R)-2-{[(tert-butoxy)carbonyl]amino}-2-cyclohexylacetic acid;(2R)-2-Cyclohexyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid;(2R)-N-(tert-Butoxycarbonyl)-2-cyclohexylglycine;(R)-tert-butoxycarbonylamino-cyclohexyl-acetic acid;(2R)-[(tert-Butoxycarbonyl)amino](cyclohexyl)acetic acid;(r)-2-(tert-butoxycarbonylamino)-2-cyclohexylacetic acid;(R)-2-(Boc-amino)-2-cyclohexylacetic Acid;(2r)-2-cyclohexyl-2-((2-methylpropan-2-yl)oxycarbonylamino)acetic acid;(2R)-2-(tert-butoxycarbonylamino)-2-cyclohexyl-acetic acid;Boc-(D)-Chg-OH;boc-d-cyclohexyl glycine;Boc-D-Chg-OH,Nonhydrate;N-Boc-D-2-cyclohexylglycine;SCHEMBL844822;DTXSID40426700;QSUXZIPXYDQFCX-SNVBAGLBSA-N;AKOS015902580;CS-W012548;HY-W011832;AC-24101;AS-19573;Boc-D-Chg-OH, >=98.0% (TLC);B4975;N-(tert-Butoxycarbonyl)-D-2-cyclohexylglycine;EN300-7383673;J-300444;(2R)-[(tert-butoxycarbonyl)amino](cyclohexyl)ethanoic acid;(2R)-[(tert-butoxycarbonyl)-amino](cyclohexyl)ethanoic acid

Chemical Property of Boc-D-Chg-OH

Chemical Property:

• Vapor Pressure: 8.56E-08mmHg at 25°C
• Melting Point: 75°C(lit.)
• Boiling Point: 407.9oC at 760 mmHg
• PKA: 4.01±0.10(Predicted)
• Flash Point: 200.5oC
• PSA: 75.63000
• Density: 1.111g/cm3
• LogP: 2.93550
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, Dichloromethane, DMSO, Ethyl Acetate
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 257.16270821
• Heavy Atom Count: 18
• Complexity: 303

Purity/Quality:

99% ^*data from raw suppliers

N-Boc-D-cyclohexylglycine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(C1CCCCC1)C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@H](C1CCCCC1)C(=O)O

Technology Process of Boc-D-Chg-OH

There total 8 articles about Boc-D-Chg-OH 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: 89.0%

di-tert-butyl dicarbonate (24424-99-5) + (R)-2-amino-2-cyclohexyl acetic acid (14328-52-0) → (2R)-[(tert-butoxycarbonyl)-amino](cyclohexyl)ethanoic acid (70491-05-3)

Guidance literature:

di-tert-butyl dicarbonate; (R)-2-amino-2-cyclohexyl acetic acid; With sodium carbonate; In water; acetone; at 20 ℃; for 16h;

With potassium hydrogensulfate; In water; pH=1;

DOI:10.1021/jm2004305

Reference yield: 78.0%

ethyl (R)-N-(tert-butoxycarbonyl)-cyclohexylglycinate (847254-57-3) → (2R)-[(tert-butoxycarbonyl)-amino](cyclohexyl)ethanoic acid (70491-05-3)

Guidance literature:

With lithium hydroxide; In 1,4-dioxane; water; at 20 ℃; for 14h;

DOI:10.1002/adsc.200404114

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (2R)-[(tert-butoxycarbonyl)-amino](cyclohexyl)ethanoic acid (70491-05-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: iodobenzene diacetate / methanol / 0.5 h / 0 °C

1.2: aq. HCl / methanol / 0.5 h / 0 °C

1.3: 67 percent / aq. Na₂CO₃ / methanol

2.1: 78 percent / LiOH / dioxane; H₂O / 14 h / 20 °C

With lithium hydroxide; [bis(acetoxy)iodo]benzene; In 1,4-dioxane; methanol; water;

DOI:10.1002/adsc.200404114

upstream raw materials:

(R)-1-(cyclohexyl-2-hydroxyethyl)carbamic acid tert-butyl ester

ethyl (R)-N-(tert-butoxycarbonyl)-cyclohexylglycinate

di-tert-butyl dicarbonate

cyclohexanone

Downstream raw materials:

tert-butyl (R)-(methoxycarbonyl)(cyclohexyl)methylcarbamate

N-Boc-Chg-Pro-OMe

(R)-1-(cyclohexyl-2-hydroxyethyl)carbamic acid tert-butyl ester

(2-tert-butoxycarbonylamino-2-cyclohexyl-acetylamino)-acetic acid methyl ester

Refernces

• 1、 Notz, Wolfgang,Watanabe, Shin-Ichi,Chowdari, Naidu S.,Zhong, Guofu,Betancort, Juan M.,Tanaka, Fujie,Barbas III, Carlos F.. "The scope of the direct proline-catalyzed asymmetric addition of ketones to imines". . p. 1131 - 1140. Retrieved 2007/10/03.
• 2、 Matsunaga, Hirofumi,Ishizuka, Tadao,Kunieda, Takehisa. "Chiral electrophilic 'glycinal' equivalents. New synthons for optically active α-amino acids and 4-substituted 2-oxazolidinones". . p. 1275 - 1294. Retrieved 2007/10/03.