(2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-2-(N-((benzyloxy)carbonyl)-amino)-5-cyclohexyl-3-hydroxy-1-phenylpentane acetonide

Base Information

Chemical Name:(2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-2-(N-((benzyloxy)carbonyl)-amino)-5-cyclohexyl-3-hydroxy-1-phenylpentane acetonide
CAS No.:148472-68-8
Molecular Formula:C₃₃H₄₆N₂O₅
Molecular Weight:550.739
Hs Code.:

Synonyms:(2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-2-(N-((benzyloxy)carbonyl)-amino)-5-cyclohexyl-3-hydroxy-1-phenylpentane acetonide

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Chemical Property of (2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-2-(N-((benzyloxy)carbonyl)-amino)-5-cyclohexyl-3-hydroxy-1-phenylpentane acetonide

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Technology Process of (2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-2-(N-((benzyloxy)carbonyl)-amino)-5-cyclohexyl-3-hydroxy-1-phenylpentane acetonide

There total 6 articles about (2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-2-(N-((benzyloxy)carbonyl)-amino)-5-cyclohexyl-3-hydroxy-1-phenylpentane acetonide 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:

: 37736-82-6
(S)-2-tert-butoxycarbonylamino-3-cyclohexylpropionic acid

: 148472-68-8
(2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-2-(N-((benzyloxy)carbonyl)-amino)-5-cyclohexyl-3-hydroxy-1-phenylpentane acetonide

Guidance literature:: Multi-step reaction with 6 steps

1: 1) DMAP, isopropenyl chloroformate / 1) CH₂Cl₂, -5 degC to 0 degC, 2 h, 2) ethyl acetate, reflux, 30 min

2: 5.58 g / sodium borohydride / CH₂Cl₂; acetic acid / 3 h

3: 1) HMPA, 2) C₆H₅CH₂Br / 1) THF, -78 degC, 50 min, 2) THF, -78 degC, 30 min

4: 1) 1M LiOH, 2) PPTS / 1) THF, 1.5 h, 2) CH₂Cl₂, r.t., 2 h

5: diphenylphosphoryl azide, Et₃N / xylene / 2 h / 90 °C

6: DMAP / 15 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; sodium tetrahydroborate; Isopropenyl chloroformate; diphenylphosphoranyl azide; pyridinium p-toluenesulfonate; benzyl bromide; triethylamine; In dichloromethane; acetic acid; xylene;
DOI:10.1016/S0040-4020(01)80342-2

Reference yield:

: 139374-78-0
(4S,5R)-N-(((tert)-butyloxy)carbonyl)-5-(cyclohexylmethyl)-4-hydroxy-2-pyrrolidinone

: 148472-68-8
(2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-2-(N-((benzyloxy)carbonyl)-amino)-5-cyclohexyl-3-hydroxy-1-phenylpentane acetonide

Guidance literature:: Multi-step reaction with 4 steps

1: 1) HMPA, 2) C₆H₅CH₂Br / 1) THF, -78 degC, 50 min, 2) THF, -78 degC, 30 min

2: 1) 1M LiOH, 2) PPTS / 1) THF, 1.5 h, 2) CH₂Cl₂, r.t., 2 h

3: diphenylphosphoryl azide, Et₃N / xylene / 2 h / 90 °C

4: DMAP / 15 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; diphenylphosphoranyl azide; pyridinium p-toluenesulfonate; benzyl bromide; triethylamine; In xylene;
DOI:10.1016/S0040-4020(01)80342-2

Reference yield:

: 148472-62-2
(5R)-N-(((tert)-butyloxy)carbonyl)-5-(cyclohexylmethyl)-2,4-pyrrolidindione

: 148472-68-8
(2R,3S,4R)-4-(N-(((tert)-butyloxy)carbonyl)-amino)-2-(N-((benzyloxy)carbonyl)-amino)-5-cyclohexyl-3-hydroxy-1-phenylpentane acetonide

Guidance literature:: Multi-step reaction with 5 steps

1: 5.58 g / sodium borohydride / CH₂Cl₂; acetic acid / 3 h

2: 1) HMPA, 2) C₆H₅CH₂Br / 1) THF, -78 degC, 50 min, 2) THF, -78 degC, 30 min

3: 1) 1M LiOH, 2) PPTS / 1) THF, 1.5 h, 2) CH₂Cl₂, r.t., 2 h

4: diphenylphosphoryl azide, Et₃N / xylene / 2 h / 90 °C

5: DMAP / 15 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; sodium tetrahydroborate; diphenylphosphoranyl azide; pyridinium p-toluenesulfonate; benzyl bromide; triethylamine; In dichloromethane; acetic acid; xylene;
DOI:10.1016/S0040-4020(01)80342-2