(2S,3S,5S)-N-<1-cyclohexyl-3-hydroxyl-6-methyl-5-<<<2-(4-morpholinyl)ethoxy>carbonyl>amino>heptan-2-yl>(tert-butyloxycarbonyl)L-histidinamide

Base Information

• Chemical Name: (2S,3S,5S)-N-<1-cyclohexyl-3-hydroxyl-6-methyl-5-<<<2-(4-morpholinyl)ethoxy>carbonyl>amino>heptan-2-yl>(tert-butyloxycarbonyl)L-histidinamide
• CAS No.: 140661-03-6
• Molecular Formula: C₃₂H₅₆N₆O₇
• Molecular Weight: 636.833
• Mol file: 140661-03-6.mol

Synonyms:(2S,3S,5S)-N-<1-cyclohexyl-3-hydroxyl-6-methyl-5-<<<2-(4-morpholinyl)ethoxy>carbonyl>amino>heptan-2-yl>(tert-butyloxycarbonyl)L-histidinamide

Chemical Property of (2S,3S,5S)-N-<1-cyclohexyl-3-hydroxyl-6-methyl-5-<<<2-(4-morpholinyl)ethoxy>carbonyl>amino>heptan-2-yl>(tert-butyloxycarbonyl)L-histidinamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,5S)-N-<1-cyclohexyl-3-hydroxyl-6-methyl-5-<<<2-(4-morpholinyl)ethoxy>carbonyl>amino>heptan-2-yl>(tert-butyloxycarbonyl)L-histidinamide

There total 4 articles about (2S,3S,5S)-N-<1-cyclohexyl-3-hydroxyl-6-methyl-5-<<<2-(4-morpholinyl)ethoxy>carbonyl>amino>heptan-2-yl>(tert-butyloxycarbonyl)L-histidinamide 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:

2-(morpholin-4-yl)ethanol (622-40-2) → (2S,3S,5S)-N-<1-cyclohexyl-3-hydroxyl-6-methyl-5-<<<2-(4-morpholinyl)ethoxy>carbonyl>amino>heptan-2-yl>(tert-butyloxycarbonyl)L-histidinamide (140661-03-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) triethylamine, diphenylphosphoryl azide / 1.) toluene, 65 deg C, 2 h, 2.) toluene, 85 deg C, 24 h

2: TFA / 1.) CH₂Cl₂, 0 deg C, 3.5 h, 2.a.) THF, H₂O, 0 deg C, 4 h, b.) THF, H₂O, RT, 12 h

3: 2.) HOAc / 1 a.) CH₂Cl₂, 0 deg C, 6 h, b.) RT, 14 h, 2.) THF, water, 50 deg C, 5 h

With diphenylphosphoranyl azide; acetic acid; triethylamine; trifluoroacetic acid;

DOI:10.1021/jm00088a007

Reference yield:

2-(S)-((3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(S)-oxazolidinyl)methyl)-3-methylbutanoic acid (129921-93-3) → (2S,3S,5S)-N-<1-cyclohexyl-3-hydroxyl-6-methyl-5-<<<2-(4-morpholinyl)ethoxy>carbonyl>amino>heptan-2-yl>(tert-butyloxycarbonyl)L-histidinamide (140661-03-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) triethylamine, diphenylphosphoryl azide / 1.) toluene, 65 deg C, 2 h, 2.) toluene, 85 deg C, 24 h

2: TFA / 1.) CH₂Cl₂, 0 deg C, 3.5 h, 2.a.) THF, H₂O, 0 deg C, 4 h, b.) THF, H₂O, RT, 12 h

3: 2.) HOAc / 1 a.) CH₂Cl₂, 0 deg C, 6 h, b.) RT, 14 h, 2.) THF, water, 50 deg C, 5 h

With diphenylphosphoranyl azide; acetic acid; triethylamine; trifluoroacetic acid;

DOI:10.1021/jm00088a007

Reference yield:

(2S,4S,5S)-1-<3-(tert-butyloxycarbonyl)-2,2-dimethyl-4-(cyclohexylmethyl)-5-oxazolidinyl>-2-<<<2-(4-morpholinyl)ethoxy>carbonyl>amino>-3-methylbutane (130317-34-9) → (2S,3S,5S)-N-<1-cyclohexyl-3-hydroxyl-6-methyl-5-<<<2-(4-morpholinyl)ethoxy>carbonyl>amino>heptan-2-yl>(tert-butyloxycarbonyl)L-histidinamide (140661-03-6)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / 1.) CH₂Cl₂, 0 deg C, 3.5 h, 2.a.) THF, H₂O, 0 deg C, 4 h, b.) THF, H₂O, RT, 12 h

2: 2.) HOAc / 1 a.) CH₂Cl₂, 0 deg C, 6 h, b.) RT, 14 h, 2.) THF, water, 50 deg C, 5 h

With acetic acid; trifluoroacetic acid;

DOI:10.1021/jm00088a007

upstream raw materials:

((1S,3S,4S)-4-Amino-5-cyclohexyl-3-hydroxy-1-isopropyl-pentyl)-carbamic acid 2-morpholin-4-yl-ethyl ester

Nα, Nim-di-Boc-L-histidine N-hydroxysuccinimide ester

2-(morpholin-4-yl)ethanol

2-(S)-((3-(tert-butyloxycarbonyl)-2,2-dimethyl-4(S)-(cyclohexylmethyl)-5(S)-oxazolidinyl)methyl)-3-methylbutanoic acid

Downstream raw materials:

(2S,3S,5S)-N-<1-cyclohexyl-3-hydroxy-6-methyl-5-<<<2-(4-morpholinyl)ethoxy>carbonyl>amino>heptan-2-yl>-L-histidinamide

{(1S,3S,4S)-4-[(S)-2-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionylamino)-3-(1H-imidazol-4-yl)-propionylamino]-5-cyclohexyl-3-hydroxy-1-isopropyl-pentyl}-carbamic acid 2-morpholin-4-yl-ethyl ester