(2R,3R,4S)-4-Benzyloxycarbonylamino-2-((R)-2-benzyloxycarbonylamino-propionylamino)-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-pentanoic acid methyl ester

Base Information

Chemical Name:(2R,3R,4S)-4-Benzyloxycarbonylamino-2-((R)-2-benzyloxycarbonylamino-propionylamino)-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-pentanoic acid methyl ester
CAS No.:81658-13-1
Molecular Formula:C₃₀H₃₉N₃O₁₀
Molecular Weight:601.654
Hs Code.:

(2R,3R,4S)-4-Benzyloxycarbonylamino-2-((R)-2-benzyloxycarbonylamino-propionylamino)-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-pentanoic acid methyl ester

Synonyms:(2R,3R,4S)-4-Benzyloxycarbonylamino-2-((R)-2-benzyloxycarbonylamino-propionylamino)-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-pentanoic acid methyl ester

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Chemical Property of (2R,3R,4S)-4-Benzyloxycarbonylamino-2-((R)-2-benzyloxycarbonylamino-propionylamino)-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-pentanoic acid methyl ester

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Technology Process of (2R,3R,4S)-4-Benzyloxycarbonylamino-2-((R)-2-benzyloxycarbonylamino-propionylamino)-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-pentanoic acid methyl ester

There total 4 articles about (2R,3R,4S)-4-Benzyloxycarbonylamino-2-((R)-2-benzyloxycarbonylamino-propionylamino)-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-pentanoic acid methyl ester 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: 76.5%

: 26607-51-2
N-benzyloxycarbonyl-D-alanine

: 81658-12-0
(2R,3S,4S)-2-Amino-4-benzyloxycarbonylamino-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-pentanoic acid methyl ester

: 81658-13-1
(2R,3R,4S)-4-Benzyloxycarbonylamino-2-((R)-2-benzyloxycarbonylamino-propionylamino)-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-pentanoic acid methyl ester

Guidance literature:: With diethyl cyanophosphonate; triethylamine;
DOI:10.1016/S0040-4039(00)87057-4

Reference yield:

: 1676-75-1
N-benzyloxycarbonyl-O-t-butyl-L-serine

: 81658-13-1
(2R,3R,4S)-4-Benzyloxycarbonylamino-2-((R)-2-benzyloxycarbonylamino-propionylamino)-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 62 percent / diphenyl phosphorazidate, K₂CO₃ sesquihydrate / dimethylformamide / 1.) 0 deg C, 2 h, 2.) room temp., 14 h

2: trifluoroacetic acid / CH₂Cl₂ / 2 h / Ambient temperature

3: 67 percent / 4-N,N-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

4: 1.) HCl, 2.) NaHCO₃, NaBH₄ / 1.) MeOH, 40 deg C, 2.5 h; 2.) EtOH, -10 deg C, 1 h

5: 76.5 percent / diethyl phosphorocyanidate, Et₃N

With hydrogenchloride; dmap; sodium tetrahydroborate; diethyl cyanophosphonate; diphenyl phosphoryl azide; sodium hydrogencarbonate; potassium carbonate; triethylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)87057-4

Reference yield:

: 81658-09-5
5-((S)-1-Benzyloxycarbonylamino-2-tert-butoxy-ethyl)-oxazole-4-carboxylic acid methyl ester

: 81658-13-1
(2R,3R,4S)-4-Benzyloxycarbonylamino-2-((R)-2-benzyloxycarbonylamino-propionylamino)-5-(2,2-dimethyl-propionyloxy)-3-hydroxy-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: trifluoroacetic acid / CH₂Cl₂ / 2 h / Ambient temperature

2: 67 percent / 4-N,N-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: 1.) HCl, 2.) NaHCO₃, NaBH₄ / 1.) MeOH, 40 deg C, 2.5 h; 2.) EtOH, -10 deg C, 1 h

4: 76.5 percent / diethyl phosphorocyanidate, Et₃N

With hydrogenchloride; dmap; sodium tetrahydroborate; diethyl cyanophosphonate; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; In dichloromethane;
DOI:10.1016/S0040-4039(00)87057-4