(S)-2-(tert-Butoxycarbonyl-{(R)-2-[tert-butoxycarbonyl-((R)-2-tert-butoxycarbonylamino-3-hydroxy-propyl)-amino]-3-hydroxy-propyl}-amino)-succinic acid dibenzyl ester

Base Information

• Chemical Name: (S)-2-(tert-Butoxycarbonyl-{(R)-2-[tert-butoxycarbonyl-((R)-2-tert-butoxycarbonylamino-3-hydroxy-propyl)-amino]-3-hydroxy-propyl}-amino)-succinic acid dibenzyl ester
• CAS No.: 91103-44-5
• Molecular Formula: C₃₉H₅₇N₃O₁₂
• Molecular Weight: 759.894
• Mol file: 91103-44-5.mol

Synonyms:

Chemical Property of (S)-2-(tert-Butoxycarbonyl-{(R)-2-[tert-butoxycarbonyl-((R)-2-tert-butoxycarbonylamino-3-hydroxy-propyl)-amino]-3-hydroxy-propyl}-amino)-succinic acid dibenzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(tert-Butoxycarbonyl-{(R)-2-[tert-butoxycarbonyl-((R)-2-tert-butoxycarbonylamino-3-hydroxy-propyl)-amino]-3-hydroxy-propyl}-amino)-succinic acid dibenzyl ester

There total 12 articles about (S)-2-(tert-Butoxycarbonyl-{(R)-2-[tert-butoxycarbonyl-((R)-2-tert-butoxycarbonylamino-3-hydroxy-propyl)-amino]-3-hydroxy-propyl}-amino)-succinic acid dibenzyl 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:

N-tert.-butyloxycarbonyl-L-serinal (91103-36-5,157683-97-1) → (S)-2-(tert-Butoxycarbonyl-{(R)-2-[tert-butoxycarbonyl-((R)-2-tert-butoxycarbonylamino-3-hydroxy-propyl)-amino]-3-hydroxy-propyl}-amino)-succinic acid dibenzyl ester (91103-44-5)

Guidance literature:

Multi-step reaction with 4 steps

1: NaBH₃CN / methanol / 1.) 0 deg C, 3 h; 2.) room temp., 14 h

2: triethylamine / tetrahydrofuran / 40 h / Ambient temperature

3: 1) O₃, 2) NaBH₃CN / 2) MeOH, 0 deg C, 3 h, to room temp., 14h

4: triethylamine / 40 h / Ambient temperature

With sodium cyanoborohydride; ozone; triethylamine; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4039(01)80104-0

Reference yield:

benzyl bromide (100-39-0) → (S)-2-(tert-Butoxycarbonyl-{(R)-2-[tert-butoxycarbonyl-((R)-2-tert-butoxycarbonylamino-3-hydroxy-propyl)-amino]-3-hydroxy-propyl}-amino)-succinic acid dibenzyl ester (91103-44-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / KOH / dimethylformamide

2: CF₃CO₂H / CH₂Cl₂

3: 1) O₃, 2) NaBH₃CN / 2) MeOH, 0 deg C, 3 h, to room temp., 14h

4: triethylamine / 40 h / Ambient temperature

With potassium hydroxide; sodium cyanoborohydride; ozone; triethylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)80104-0

Reference yield:

((R)-1-Hydroxymethyl-3-methanesulfinyl-propyl)-carbamic acid tert-butyl ester (91103-40-1) → (S)-2-(tert-Butoxycarbonyl-{(R)-2-[tert-butoxycarbonyl-((R)-2-tert-butoxycarbonylamino-3-hydroxy-propyl)-amino]-3-hydroxy-propyl}-amino)-succinic acid dibenzyl ester (91103-44-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 65 percent / o-dichlorobenzene/NaOAc / 20 h / 170 °C

2: 1) O₃, 2) dimethylsulfide / 1) MeOH, -78 deg C, 2) -78 deg C, 3 h to room temp., 1 h

3: NaBH₃CN / methanol / 1.) 0 deg C, 3 h; 2.) room temp., 14 h

4: triethylamine / tetrahydrofuran / 40 h / Ambient temperature

5: 1) O₃, 2) NaBH₃CN / 2) MeOH, 0 deg C, 3 h, to room temp., 14h

6: triethylamine / 40 h / Ambient temperature

With dimethylsulfide; sodium acetate; sodium cyanoborohydride; ozone; triethylamine; 1,2-dichloro-benzene; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4039(01)80104-0

upstream raw materials:

di-tert-butyl dicarbonate

(S)-2-{(R)-2-[tert-Butoxycarbonyl-((R)-2-tert-butoxycarbonylamino-3-hydroxy-propyl)-amino]-3-hydroxy-propylamino}-succinic acid dibenzyl ester

dibenzyl L-aspartate

N-tert.-butyloxycarbonyl-L-serinal