benzyl (S)-2-tert-butoxycarbonylamino-5-benzyloxypentanoate

Base Information

• Chemical Name: benzyl (S)-2-tert-butoxycarbonylamino-5-benzyloxypentanoate
• CAS No.: 370867-50-8
• Molecular Formula: C₂₄H₃₁NO₅
• Molecular Weight: 413.514
• Mol file: 370867-50-8.mol

Synonyms:benzyl (S)-2-tert-butoxycarbonylamino-5-benzyloxypentanoate

Chemical Property of benzyl (S)-2-tert-butoxycarbonylamino-5-benzyloxypentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (S)-2-tert-butoxycarbonylamino-5-benzyloxypentanoate

There total 3 articles about benzyl (S)-2-tert-butoxycarbonylamino-5-benzyloxypentanoate 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: 82.0%

benzyl bromide (100-39-0) + (S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester (91229-97-9) → benzyl (S)-2-tert-butoxycarbonylamino-5-benzyloxypentanoate (370867-50-8)

Guidance literature:

With silver(l) oxide; In diethyl ether;

DOI:10.1016/S0040-4039(01)01136-4

Reference yield:

Boc-Glu-OBn (30924-93-7) → benzyl (S)-2-tert-butoxycarbonylamino-5-benzyloxypentanoate (370867-50-8)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / tetrahydrofuran / 1 h / -10 °C

2: 2.86 g / NaBH₄ / tetrahydrofuran; H₂O / 3 h / -10 - 20 °C

3: 82 percent / Ag₂O / diethyl ether / 14 h

With sodium tetrahydroborate; triethylamine; silver(l) oxide; In tetrahydrofuran; diethyl ether; water;

DOI:10.1016/j.tet.2004.12.009

Reference yield:

2-tert-butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester (105589-11-5) → benzyl (S)-2-tert-butoxycarbonylamino-5-benzyloxypentanoate (370867-50-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.86 g / NaBH₄ / tetrahydrofuran; H₂O / 3 h / -10 - 20 °C

2: 82 percent / Ag₂O / diethyl ether / 14 h

With sodium tetrahydroborate; silver(l) oxide; In tetrahydrofuran; diethyl ether; water;

DOI:10.1016/j.tet.2004.12.009

upstream raw materials:

benzyl bromide

(S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester

Boc-Glu-OBn

2-tert-butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester

Downstream raw materials:

(S)-5-Benzyloxy-2-tert-butoxycarbonylamino-pentanoic acid

C₇₂H₁₀₁N₆O₁₅PSi₂

2-{[2-(5-benzyloxy-2-tert-butoxycarbonylamino-pentanoylamino)-3-phenyl-propionyl]-methyl-amino}-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid methyl ester

C₇₂H₁₀₁N₆O₁₅PSi₂