(S)-3-[1-(Benzyloxycarbonylamino-carboxy-methyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-propionic acid methyl ester

Base Information

• Chemical Name: (S)-3-[1-(Benzyloxycarbonylamino-carboxy-methyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-propionic acid methyl ester
• CAS No.: 145396-87-8
• Molecular Formula: C₂₇H₃₁N₃O₈
• Molecular Weight: 525.558
• Mol file: 145396-87-8.mol

Synonyms:

Chemical Property of (S)-3-[1-(Benzyloxycarbonylamino-carboxy-methyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-[1-(Benzyloxycarbonylamino-carboxy-methyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-propionic acid methyl ester

There total 1 articles about (S)-3-[1-(Benzyloxycarbonylamino-carboxy-methyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-propionic 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: 64.0%

O-benzyl carbamate (621-84-1) + methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate (141215-69-2,33900-28-6) + Glyoxilic acid (298-12-4) → (S)-3-[1-(Benzyloxycarbonylamino-carboxy-methyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-propionic acid methyl ester (145396-87-8,145396-94-7)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; for 12h;

DOI:10.1039/c39920001353

Reference yield:

H-Val-Gly-OTMSE (145396-95-8) + (S)-3-[1-(Benzyloxycarbonylamino-carboxy-methyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-propionic acid methyl ester (145396-87-8,145396-94-7) → (S)-3-[1-((S)-Benzyloxycarbonylamino-{(S)-2-methyl-1-[(2-trimethylsilanyl-ethoxycarbonylmethyl)-carbamoyl]-propylcarbamoyl}-methyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-propionic acid methyl ester (145396-88-9,145511-88-2) + (S)-3-[1-((R)-Benzyloxycarbonylamino-{(S)-2-methyl-1-[(2-trimethylsilanyl-ethoxycarbonylmethyl)-carbamoyl]-propylcarbamoyl}-methyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-propionic acid methyl ester (145396-88-9,145511-88-2)

Guidance literature:

With diphenylphosphoranyl azide; In N,N-dimethyl-formamide; at 4 ℃; for 48h; Yield given. Yields of byproduct given;

DOI:10.1039/c39920001353

Reference yield:

(S)-3-[1-(Benzyloxycarbonylamino-carboxy-methyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-propionic acid methyl ester (145396-87-8,145396-94-7) → (S)-3-[1-((S)-Benzyloxycarbonylamino-{(S)-2-methyl-1-[(2-trimethylsilanyl-ethoxycarbonylmethyl)-carbamoyl]-propylcarbamoyl}-methyl)-1H-indol-3-yl]-2-((S)-2-tert-butoxycarbonylamino-3-hydroxy-propionylamino)-propionic acid methyl ester (145396-89-0,145511-89-3)

Guidance literature:

Multi-step reaction with 3 steps

1: diphenylphosphoryl azide (DPPA) / dimethylformamide / 48 h / 4 °C

2: HCl / dioxane / 1 h / 20 °C

3: dimethylformamide / 16 h / 20 °C

With hydrogenchloride; diphenylphosphoranyl azide; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1039/c39920001353

upstream raw materials:

O-benzyl carbamate

methyl (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(1H-indol-3-yl)propanoate

Glyoxilic acid

Downstream raw materials:

(S)-3-[1-((S)-Benzyloxycarbonylamino-{(S)-2-methyl-1-[(2-trimethylsilanyl-ethoxycarbonylmethyl)-carbamoyl]-propylcarbamoyl}-methyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-propionic acid methyl ester

(S)-3-[1-((R)-Benzyloxycarbonylamino-{(S)-2-methyl-1-[(2-trimethylsilanyl-ethoxycarbonylmethyl)-carbamoyl]-propylcarbamoyl}-methyl)-1H-indol-3-yl]-2-tert-butoxycarbonylamino-propionic acid methyl ester

(S)-3-[1-((S)-Benzyloxycarbonylamino-{(S)-2-methyl-1-[(2-trimethylsilanyl-ethoxycarbonylmethyl)-carbamoyl]-propylcarbamoyl}-methyl)-1H-indol-3-yl]-2-((S)-2-tert-butoxycarbonylamino-3-hydroxy-propionylamino)-propionic acid methyl ester

(S)-3-[1-((R)-Benzyloxycarbonylamino-{(S)-2-methyl-1-[(2-trimethylsilanyl-ethoxycarbonylmethyl)-carbamoyl]-propylcarbamoyl}-methyl)-1H-indol-3-yl]-2-((S)-2-tert-butoxycarbonylamino-3-hydroxy-propionylamino)-propionic acid methyl ester