Boc-achpa

Base Information

• Chemical Name: Boc-achpa
• CAS No.: 98105-45-4
• Molecular Formula: C16H29NO5
• Molecular Weight: 315.41
• Hs Code.: 29225090
• DSSTox Substance ID: DTXSID60913445
• Wikidata: Q82884048
• Mol file: 98105-45-4.mol

Synonyms:Boc-ACHPA;tert-butyloxycarbonyl-4-amino-3-hydroxy-5-cyclohexylpentanoic acid

Chemical Property of Boc-achpa

Chemical Property:

• Vapor Pressure: 5.23E-12mmHg at 25°C
• Refractive Index: 1.497
• Boiling Point: 498.1 °C at 760 mmHg
• Flash Point: 255 °C
• PSA: 95.86000
• Density: 1.121 g/cm³
• LogP: 3.07660
• Storage Temp.: −20°C
• XLogP3: 3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 315.20457303
• Heavy Atom Count: 22
• Complexity: 371

Purity/Quality:

98%Min ^*data from raw suppliers

Boc-(3S,4S)-4-amino-3-hydroxy-5-cyclohexylpentanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1CCCCC1)C(CC(=O)O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1CCCCC1)[C@H](CC(=O)O)O
• Uses: Boc-(3S,4S)-4-amino-3-hydroxy-5-cyclohexylpentanoic Acid, Boc-5-Cyclohexylstatine

Technology Process of Boc-achpa

There total 10 articles about Boc-achpa 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: 97.0%

(3S)-3-hydroxy-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester (98105-43-2) → (3S,4S)-4-(N-tert-butoxycarbonyl)amino-5-cyclohexyl-3-hydroxypentanoic acid (98105-45-4)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; water; for 1h;

DOI:10.1021/jm00150a007

Reference yield:

(3S,4S)-4-tert-butoxycarbonylamino-3-hydroxy-5-phenylpentanoic acid (72155-48-7) → (3S,4S)-4-(N-tert-butoxycarbonyl)amino-5-cyclohexyl-3-hydroxypentanoic acid (98105-45-4)

Guidance literature:

With hydrogen; rhodium on alumina; In ethanol; for 16h; under 3040 - 3800 Torr; Yield given;

DOI:10.1248/cpb.38.103

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (3S,4S)-4-(N-tert-butoxycarbonyl)amino-5-cyclohexyl-3-hydroxypentanoic acid (98105-45-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 99.5 percent / NaHCO₃ / dimethylformamide / 120 h

2: 98.2 percent / dihydrogen / 5percent Rh/Al₂O₃ / methanol / 18 h / 1551.4 - 2844.3 Torr

3: 80 percent / diisobutylaluminum hydride (Dibal), CH₃OH / toluene; hexane / 2 h / -78 °C

4: 1.) diisopropylamine, n-BuLi / 1.) dioxane, hexane, -78 deg C, 15 min, 2.) THF, dioxane, hexane, -78 deg C, 5 min

5: 97 percent / 2 N NaOH / dioxane; H₂O / 1 h

With methanol; sodium hydroxide; n-butyllithium; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; diisopropylamine; Rh/Al₂O₃; In 1,4-dioxane; methanol; hexane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm00150a007

upstream raw materials:

(3S,4S)-4-tert-butoxycarbonylamino-3-hydroxy-5-phenylpentanoic acid

(3S)-3-hydroxy-(4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexylpentanoic acid ethyl ester

(S)-4-tert-Butoxycarbonylamino-5-cyclohexyl-3-hydroxy-pentanoic acid ethyl ester

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

((1S,2S)-3-{(S)-1-[3-(Benzyloxycarbonylamino-methyl)-benzylcarbamoyl]-3-methyl-butylcarbamoyl}-1-cyclohexylmethyl-2-hydroxy-propyl)-carbamic acid tert-butyl ester

(S)-2-[(2S,3S)-2-((3S,4S)-4-tert-Butoxycarbonylamino-5-cyclohexyl-3-hydroxy-pentanoylamino)-3-methyl-pentanoylamino]-3-phenyl-propionic acid methyl ester

Boc-ACHP-Ile-(3-pyridylmethyl)amide

(S,S)-γ-amino-β-hydroxy-N-<2-(4-morpholinyl)ethyl>cyclohexane pentanamide

Refernces

• 1、 Kahn,Nakanishi,Chrusciel,Fitzpatrick,Johnson. "Examination of HIV-1 protease secondary structure specificity using conformationally constrained inhibitors [1]". . p. 3395 - 3399. Retrieved 2007/10/02.
• 2、 Roberts, David A.,Bradbury, Robert H.,Brown, David,Faull, Alan,Griffiths, David,et al.. "1,2,4-Triazolopyrazine Derivatives with Human Renin Inhibitory Activity. 1. Synthesis and Biological Properties of Alkyl Alcohol and Statine Derivatives". . p. 2326 - 2334. Retrieved 2007/10/02.