3-[5-benzyloxycarbonyl-3-(5-benzyloxycarbonyl-3-tert-butoxycarbonylamino-pentanoylamino)-pentanoylamino]-hexanedioic acid 6-benzyl ester 1-tert-butyl ester

Base Information

• Chemical Name: 3-[5-benzyloxycarbonyl-3-(5-benzyloxycarbonyl-3-tert-butoxycarbonylamino-pentanoylamino)-pentanoylamino]-hexanedioic acid 6-benzyl ester 1-tert-butyl ester
• CAS No.: 932019-56-2
• Molecular Formula: C₄₈H₆₃N₃O₁₂
• Molecular Weight: 874.041
• Mol file: 932019-56-2.mol

Synonyms:3-[5-benzyloxycarbonyl-3-(5-benzyloxycarbonyl-3-tert-butoxycarbonylamino-pentanoylamino)-pentanoylamino]-hexanedioic acid 6-benzyl ester 1-tert-butyl ester

Chemical Property of 3-[5-benzyloxycarbonyl-3-(5-benzyloxycarbonyl-3-tert-butoxycarbonylamino-pentanoylamino)-pentanoylamino]-hexanedioic acid 6-benzyl ester 1-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[5-benzyloxycarbonyl-3-(5-benzyloxycarbonyl-3-tert-butoxycarbonylamino-pentanoylamino)-pentanoylamino]-hexanedioic acid 6-benzyl ester 1-tert-butyl ester

There total 6 articles about 3-[5-benzyloxycarbonyl-3-(5-benzyloxycarbonyl-3-tert-butoxycarbonylamino-pentanoylamino)-pentanoylamino]-hexanedioic acid 6-benzyl ester 1-tert-butyl 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: 65.0%

3-amino-hexanedioic acid 6-benzyl ester 1-tert-butyl ester; hydrochloride + 3-(5-benzyloxycarbonyl-3-tert-butoxycarbonylamino-pentanoylamino)-hexanedioic acid 6-benzyl ester (932019-54-0) → 3-[5-benzyloxycarbonyl-3-(5-benzyloxycarbonyl-3-tert-butoxycarbonylamino-pentanoylamino)-pentanoylamino]-hexanedioic acid 6-benzyl ester 1-tert-butyl ester (932019-56-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 39h;

DOI:10.1021/ol0629622

Reference yield:

(3S)-3-tert-butoxycarbonylamino-5-benzyloxycarbonylpentanoic acid (218943-30-7) → 3-[5-benzyloxycarbonyl-3-(5-benzyloxycarbonyl-3-tert-butoxycarbonylamino-pentanoylamino)-pentanoylamino]-hexanedioic acid 6-benzyl ester 1-tert-butyl ester (932019-56-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / triethylamine / dimethylformamide / 2.5 h / 0 - 20 °C

2: HCl / dioxane

3: 96 percent / N,N-diisopropylethylamine; HATU / dimethylformamide / 21 h / 0 - 20 °C

4: 68 percent / acetic acid; zinc / dimethylformamide; H₂O / 3 h / 20 °C

5: 65 percent / N,N-diisopropylethylamine; HATU / dimethylformamide / 39 h / 0 - 20 °C

With hydrogenchloride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; zinc; In 1,4-dioxane; water; N,N-dimethyl-formamide;

DOI:10.1021/ol0629622

Reference yield:

3-tert-butoxycarbonylamino-hexanedioic acid 6-benzyl ester 1-tert-butyl ester (147471-67-8) → 3-[5-benzyloxycarbonyl-3-(5-benzyloxycarbonyl-3-tert-butoxycarbonylamino-pentanoylamino)-pentanoylamino]-hexanedioic acid 6-benzyl ester 1-tert-butyl ester (932019-56-2)

Guidance literature:

Multi-step reaction with 2 steps

1: HCl / dioxane / 0 °C

2: 65 percent / N,N-diisopropylethylamine; HATU / dimethylformamide / 39 h / 0 - 20 °C

With hydrogenchloride; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/ol0629622

upstream raw materials:

3-(5-benzyloxycarbonyl-3-tert-butoxycarbonylamino-pentanoylamino)-hexanedioic acid 6-benzyl ester

3-tert-butoxycarbonylamino-hexanedioic acid 6-benzyl ester 1-tert-butyl ester

3-tert-butoxycarbonylamino-hexanedioic acid 6-benzyl ester 1-(2-oxo-2-phenyl-ethyl) ester

3-(5-benzyloxycarbonyl-3-tert-butoxycarbonylamino-pentanoylamino)-hexanedioic acid 6-benzyl ester 1-(2-oxo-2-phenyl-ethyl) ester

Refernces