(S)-(-)-2-(Boc-amino)-3-cyclohexyl-1-propanol

Base Information

• Chemical Name: (S)-(-)-2-(Boc-amino)-3-cyclohexyl-1-propanol
• CAS No.: 103322-56-1
• Molecular Formula: C14H27NO3
• Molecular Weight: 257.373
• Hs Code.: 2924299090
• European Community (EC) Number: 623-110-6
• DSSTox Substance ID: DTXSID10453124
• Nikkaji Number: J904.104D
• Wikidata: Q72448013
• Mol file: 103322-56-1.mol

Synonyms:103322-56-1;Boc-Beta-Cyclohexyl-L-Alaninol;(S)-(-)-2-(Boc-amino)-3-cyclohexyl-1-propanol;tert-butyl N-[(2S)-1-cyclohexyl-3-hydroxypropan-2-yl]carbamate;Boc-3-Cyclohexyl-L-alaninol;(S)-N-Boc-2-amino-3-cyclohexylpropanol;(S)-2-(Boc-amino)-3-cyclohexylpropan-1-ol;(S)-tert-butyl 1-cyclohexyl-3-hydroxypropan-2-ylcarbamate;tert-Butyl (S)-(1-cyclohexyl-3-hydroxypropan-2-yl)carbamate;Boc-b-cyclohexyl-l-alaninol;(s)-(-)-2-N-Bco-3-cyclohexyl-1-propanol;Boc-Cha-ol;(S)-(-)-2-(tert-Butoxycarbonylamino)-3-cyclohexyl-1-propanol;(S)-()-2-(Boc-amino)-3-cyclohexyl-1-propanol;SCHEMBL57254;DTXSID10453124;BOJQBBXPSVGTQT-LBPRGKRZSA-N;(S)-tert-butyl (1-cyclohexyl-3-hydroxypropan-2-yl)carbamate;MFCD00076899;AKOS022177886;AC-5483;BS-53147;CS-0154484;C77720;EN300-12442581;J-000937;(2S)-2-(tert-Butoxycarbonylamino)-3-cyclohexyl-1-propanol;(S)-(-)-2-(Boc-amino)-3-cyclohexyl-1-propanol, 90%;tert-butyl (S)-3-cyclohexyl-1-hydroxypropan-2-ylcarbamate;tert-Butyl [(2S)-1-cyclohexyl-3-hydroxypropan-2-yl]carbamate;tert-butyl-[(1S)-2-cyclohexyl-1-(hydroxymethyl)ethyl]carbamate;tert-butyl[(1S)-2-cyclohexyl-1-(hydroxymethyl)ethyl]carbamate;[(S)-1-(Cyclohexylmethyl)-2-hydroxyethyl]carbamic acid tert-butyl ester;1,1-dimethylethyl [(1S)-2-cyclohexyl-1-(hydroxymethyl)ethyl]carbamate;Carbamicacid,N-[(1S)-2-cyclohexyl-1-(hydroxymethyl)ethyl]-,1,1-dimethylethyl ester

Chemical Property of (S)-(-)-2-(Boc-amino)-3-cyclohexyl-1-propanol

Chemical Property:

• Appearance/Colour: UN 3272
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: n20/D 1.464(lit.)
• Boiling Point: 385.436 °C at 760 mmHg
• Flash Point: 186.905 °C
• PSA: 58.56000
• Density: 1.016 g/cm³
• LogP: 3.23330
• Storage Temp.: -15°C
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 257.19909372
• Heavy Atom Count: 18
• Complexity: 254

Purity/Quality:

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

Boc-b-Cyclohexylalaninol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1CCCCC1)CO
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1CCCCC1)CO
• Uses: Precursor to (S)-N-t-Boc-cyclohexylalaninal. This precursor was oxidized to the corresponding α-amino aldehyde in good yield and high optical purity.

Technology Process of (S)-(-)-2-(Boc-amino)-3-cyclohexyl-1-propanol

There total 14 articles about (S)-(-)-2-(Boc-amino)-3-cyclohexyl-1-propanol 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: 100.0%

(S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol (66605-57-0) → tert-butyl [(1S)-2-cyclohexyl-1-(hydroxymethyl)ethyl]carbamate (103322-56-1)

Guidance literature:

With 5% rhodium-on-charcoal; hydrogen; at 20 ℃;

DOI:10.1021/acs.jmedchem.5b01146

Reference yield: 92.0%

di-tert-butyl dicarbonate (24424-99-5) + (2S)-2-amino-3-cyclohexylpropan-1-ol hydrochloride (117160-99-3) → tert-butyl [(1S)-2-cyclohexyl-1-(hydroxymethyl)ethyl]carbamate (103322-56-1)

Guidance literature:

With sodium hydrogencarbonate; In 1,4-dioxane; water; at 0 - 20 ℃;

Reference yield:

(2-cyclohexyl-1-hydroxymethyl-vinyl)-carbamic acid tert-butyl ester (251325-59-4) → tert-butyl [(1S)-2-cyclohexyl-1-(hydroxymethyl)ethyl]carbamate (103322-56-1)

Guidance literature:

With hydrogen; (+)-1,2-bis-((2S,5S)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I) trifluoromethanesulfonate; In tetrahydrofuran; at 20 - 25 ℃; for 12h; under 1551.44 Torr;

DOI:10.1016/S0040-4039(99)01376-3

upstream raw materials:

di-tert-butyl dicarbonate

(2S)-2-amino-3-cyclohexyl-1-propanol

(S)-2-tert-butoxycarbonylamino-3-cyclohexylpropionic acid

(S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol

Downstream raw materials:

(S)-2-(t-butoxycarbonylamino)-3-cyclohexyl-1-propanal

(2S)-2-amino-3-cyclohexyl-1-propanol

(2S)-2-amino-3-cyclohexylpropan-1-ol hydrochloride

1,1-dimethylethyl [(1S)-2-azido-1-(cyclohexylmethyl)ethyl]methylcarbamate

Refernces

• 1、 -. "NOVEL CYP34A-SPECIFIC INHIBITORS AND METHODS OF USING SAME". Page/Page column 41. . Retrieved 2017/03/28.
• 2、 Seefeld, Mark A.,Rouse, Meagan B.,McNulty, Kenneth C.,Sun, Lihui,Wang, Jizhou,Yamashita, Dennis S.,Luengo, Juan I.,Zhang, ShuYun,Minthorn, Elisabeth A.,Concha, Nestor O.,Heerding, Dirk A.. "Discovery of 5-pyrrolopyridinyl-2-thiophenecarboxamides as potent AKT kinase inhibitors". scheme or table. p. 2244 - 2248. Retrieved 2009/12/07.