(S)-3-{(2S,3R,4R,5S)-5-[(S)-2-((S)-2-tert-Butoxycarbonylamino-pentanoylamino)-4-methylsulfanyl-butyrylamino]-2,3,4,6-tetrahydroxy-hexanoylamino}-3-phenyl-propionic acid benzhydryl ester

Base Information

• Chemical Name: (S)-3-{(2S,3R,4R,5S)-5-[(S)-2-((S)-2-tert-Butoxycarbonylamino-pentanoylamino)-4-methylsulfanyl-butyrylamino]-2,3,4,6-tetrahydroxy-hexanoylamino}-3-phenyl-propionic acid benzhydryl ester
• CAS No.: 444718-62-1
• Molecular Formula: C₄₃H₅₈N₄O₁₁S
• Molecular Weight: 839.02
• Mol file: 444718-62-1.mol

Synonyms:(S)-3-{(2S,3R,4R,5S)-5-[(S)-2-((S)-2-tert-Butoxycarbonylamino-pentanoylamino)-4-methylsulfanyl-butyrylamino]-2,3,4,6-tetrahydroxy-hexanoylamino}-3-phenyl-propionic acid benzhydryl ester

Chemical Property of (S)-3-{(2S,3R,4R,5S)-5-[(S)-2-((S)-2-tert-Butoxycarbonylamino-pentanoylamino)-4-methylsulfanyl-butyrylamino]-2,3,4,6-tetrahydroxy-hexanoylamino}-3-phenyl-propionic acid benzhydryl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-{(2S,3R,4R,5S)-5-[(S)-2-((S)-2-tert-Butoxycarbonylamino-pentanoylamino)-4-methylsulfanyl-butyrylamino]-2,3,4,6-tetrahydroxy-hexanoylamino}-3-phenyl-propionic acid benzhydryl ester

There total 3 articles about (S)-3-{(2S,3R,4R,5S)-5-[(S)-2-((S)-2-tert-Butoxycarbonylamino-pentanoylamino)-4-methylsulfanyl-butyrylamino]-2,3,4,6-tetrahydroxy-hexanoylamino}-3-phenyl-propionic acid benzhydryl 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: 67.0%

N-[(2S,3R,4R,5S)-5-amino-2,3,4,6-tetrahydroxyhexanoyl]-β-D-phenylalanine diphenylmethyl ester hydrochloride + Boc-Nva-Met (712300-54-4) → (S)-3-{(2S,3R,4R,5S)-5-[(S)-2-((S)-2-tert-Butoxycarbonylamino-pentanoylamino)-4-methylsulfanyl-butyrylamino]-2,3,4,6-tetrahydroxy-hexanoylamino}-3-phenyl-propionic acid benzhydryl ester (444718-62-1)

Guidance literature:

With 1-ethyl-3-(3-dimethylaminopropyl)-3-ethylcarbodimide*HCl; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.7164/antibiotics.55.499

Reference yield:

diazodiphenylmethane (908093-98-1) → (S)-3-{(2S,3R,4R,5S)-5-[(S)-2-((S)-2-tert-Butoxycarbonylamino-pentanoylamino)-4-methylsulfanyl-butyrylamino]-2,3,4,6-tetrahydroxy-hexanoylamino}-3-phenyl-propionic acid benzhydryl ester (444718-62-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / aq. HCl / methanol / 1.5 h / 20 °C

2: 67 percent / 1-ethyl-3-(3-dimethylaminopropyl)-3-ethylcarbodimide*HCl; HOBt; iPr₂NEt / dimethylformamide / 0 - 20 °C

With hydrogenchloride; 1-ethyl-3-(3-dimethylaminopropyl)-3-ethylcarbodimide*HCl; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.55.499

Reference yield:

N-[(2S,3R,4R,5S)-5-amino-2,3,4,6-tetrahydroxyhexanoyl]-β-D-phenylalanine (219812-79-0) → (S)-3-{(2S,3R,4R,5S)-5-[(S)-2-((S)-2-tert-Butoxycarbonylamino-pentanoylamino)-4-methylsulfanyl-butyrylamino]-2,3,4,6-tetrahydroxy-hexanoylamino}-3-phenyl-propionic acid benzhydryl ester (444718-62-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / aq. HCl / methanol / 1.5 h / 20 °C

2: 67 percent / 1-ethyl-3-(3-dimethylaminopropyl)-3-ethylcarbodimide*HCl; HOBt; iPr₂NEt / dimethylformamide / 0 - 20 °C

With hydrogenchloride; 1-ethyl-3-(3-dimethylaminopropyl)-3-ethylcarbodimide*HCl; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.7164/antibiotics.55.499

upstream raw materials:

Boc-Nva-Met

diazodiphenylmethane

N-[(2S,3R,4R,5S)-5-amino-2,3,4,6-tetrahydroxyhexanoyl]-β-D-phenylalanine