(2S,3R)-3-((S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-methyl-amino}-3-phenyl-propionyloxy)-2-tert-butoxycarbonylamino-butyric acid

Base Information

Chemical Name:(2S,3R)-3-((S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-methyl-amino}-3-phenyl-propionyloxy)-2-tert-butoxycarbonylamino-butyric acid
CAS No.:220657-11-4
Molecular Formula:C₃₈H₅₂N₄O₁₀
Molecular Weight:724.852
Hs Code.:

(2S,3R)-3-((S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-methyl-amino}-3-phenyl-propionyloxy)-2-tert-butoxycarbonylamino-butyric acid

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Chemical Property of (2S,3R)-3-((S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-methyl-amino}-3-phenyl-propionyloxy)-2-tert-butoxycarbonylamino-butyric acid

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Technology Process of (2S,3R)-3-((S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-methyl-amino}-3-phenyl-propionyloxy)-2-tert-butoxycarbonylamino-butyric acid

There total 6 articles about (2S,3R)-3-((S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-methyl-amino}-3-phenyl-propionyloxy)-2-tert-butoxycarbonylamino-butyric acid 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:

: 1161-13-3
N-Cbz-L-Phe

: 220657-11-4
(2S,3R)-3-((S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-methyl-amino}-3-phenyl-propionyloxy)-2-tert-butoxycarbonylamino-butyric acid

Guidance literature:: Multi-step reaction with 5 steps

1: 94 percent / KOH, nBu₄NHSO₄ / tetrahydrofuran / 0.5 h / Ambient temperature

2: 64 percent / Et₃N, DMAP, isopropenyl chloroformate / CH₂Cl₂ / 1 h / 0 °C

3: 93 percent / H₂ / Pd/C / methanol; ethyl acetate / 3 h / 2068.59 Torr

4: 1.) BOP-Cl, NMM, 2.) NMM / 1.) CH₂Cl₂, -15 deg C, 0.5 h, 2.) 0 deg C, 6 h

5: MgBr₂*Et₂O / CH₂Cl₂ / 1.) -20 deg C, 1 h, 2.) 0 deg C, 3.5 h

With 4-methyl-morpholine; dmap; potassium hydroxide; Isopropenyl chloroformate; hydrogen; tetra(n-butyl)ammonium hydrogensulfate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; magnesium bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4020(98)01042-4

Reference yield:

: 2899-07-2
(S)-N-benzyloxycarbonyl-N-methyl-phenyl alanine

: 220657-11-4
(2S,3R)-3-((S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-methyl-amino}-3-phenyl-propionyloxy)-2-tert-butoxycarbonylamino-butyric acid

Guidance literature:: Multi-step reaction with 4 steps

1: 64 percent / Et₃N, DMAP, isopropenyl chloroformate / CH₂Cl₂ / 1 h / 0 °C

2: 93 percent / H₂ / Pd/C / methanol; ethyl acetate / 3 h / 2068.59 Torr

3: 1.) BOP-Cl, NMM, 2.) NMM / 1.) CH₂Cl₂, -15 deg C, 0.5 h, 2.) 0 deg C, 6 h

4: MgBr₂*Et₂O / CH₂Cl₂ / 1.) -20 deg C, 1 h, 2.) 0 deg C, 3.5 h

With 4-methyl-morpholine; dmap; Isopropenyl chloroformate; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; magnesium bromide; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4020(98)01042-4

Reference yield:

: 126587-71-1
Boc-threonine [(2-trimethylsilyl)ethoxy]methyl ester

: 220657-11-4
(2S,3R)-3-((S)-2-{[(S)-1-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoyl)-pyrrolidine-2-carbonyl]-methyl-amino}-3-phenyl-propionyloxy)-2-tert-butoxycarbonylamino-butyric acid

Guidance literature:: Multi-step reaction with 4 steps

1: 64 percent / Et₃N, DMAP, isopropenyl chloroformate / CH₂Cl₂ / 1 h / 0 °C

2: 93 percent / H₂ / Pd/C / methanol; ethyl acetate / 3 h / 2068.59 Torr

3: 1.) BOP-Cl, NMM, 2.) NMM / 1.) CH₂Cl₂, -15 deg C, 0.5 h, 2.) 0 deg C, 6 h

4: MgBr₂*Et₂O / CH₂Cl₂ / 1.) -20 deg C, 1 h, 2.) 0 deg C, 3.5 h

With 4-methyl-morpholine; dmap; Isopropenyl chloroformate; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; magnesium bromide; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate;
DOI:10.1016/S0040-4020(98)01042-4