2-tert-butoxycarbonylamino-5-methanesulfonyloxy-pentanoic acid benzyl ester

Base Information

• Chemical Name: 2-tert-butoxycarbonylamino-5-methanesulfonyloxy-pentanoic acid benzyl ester
• CAS No.: 256390-71-3
• Molecular Formula: C₁₈H₂₇NO₇S
• Molecular Weight: 401.481
• Mol file: 256390-71-3.mol

Synonyms:2-tert-butoxycarbonylamino-5-methanesulfonyloxy-pentanoic acid benzyl ester

Chemical Property of 2-tert-butoxycarbonylamino-5-methanesulfonyloxy-pentanoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-tert-butoxycarbonylamino-5-methanesulfonyloxy-pentanoic acid benzyl ester

There total 7 articles about 2-tert-butoxycarbonylamino-5-methanesulfonyloxy-pentanoic acid benzyl 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: 99.0%

(S)-2-[N-(tert-butoxycarbonyl)amino]-5-hydroxypentanoic acid benzyl ester (91229-97-9) + methanesulfonyl chloride (124-63-0) → 2-tert-butoxycarbonylamino-5-methanesulfonyloxy-pentanoic acid benzyl ester (256390-71-3)

Guidance literature:

With TEA; In dichloromethane; at -20 ℃; for 3h;

DOI:10.1016/S0960-894X(99)00546-6

Reference yield:

Boc-Glu-OBn (30924-93-7) → 2-tert-butoxycarbonylamino-5-methanesulfonyloxy-pentanoic acid benzyl ester (256390-71-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / EDC / CH₂Cl₂

2: 84 percent / NaBH₄ / tetrahydrofuran / 24 h / 4 °C

3: 99 percent / TEA / CH₂Cl₂ / 3 h / -20 °C

With sodium tetrahydroborate; TEA; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; dichloromethane; 1: Substitution / 2: Reduction / 3: mesylation;

DOI:10.1016/S0960-894X(99)00546-6

Reference yield:

2-tert-butoxycarbonylamino-5-ethoxycarbonyloxy-5-oxo-pentanoic acid benzyl ester (105589-11-5) → 2-tert-butoxycarbonylamino-5-methanesulfonyloxy-pentanoic acid benzyl ester (256390-71-3)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / tetrahydrofuran; methanol / 0.33 h / -10 - 0 °C

2: Et₃N / CH₂Cl₂ / 2 h / 0 °C

With sodium tetrahydroborate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 1: Reduction / 2: Condensation;

DOI:10.1021/jm9803727

upstream raw materials:

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

methanesulfonyl chloride

Boc-Glu-OBn

benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

Downstream raw materials:

(S)-2-Amino-5-methanesulfonyloxy-pentanoic acid benzyl ester

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

H-Pro-OBzl

(S)-benzyl 5-azido-2-(tert-butoxycarbonylamino)pentanoate