2(S)-2-[(3R,4S,5R)-5-benzyloxy-3-(fluorenyloxycarbonylamino)-4-hydroxy-2-oxo-1-piperidinyl]isohexanoic acid

Base Information

• Chemical Name: 2(S)-2-[(3R,4S,5R)-5-benzyloxy-3-(fluorenyloxycarbonylamino)-4-hydroxy-2-oxo-1-piperidinyl]isohexanoic acid
• CAS No.: 646057-74-1
• Molecular Formula: C₃₃H₃₆N₂O₇
• Molecular Weight: 572.658
• Mol file: 646057-74-1.mol

Synonyms:2(S)-2-[(3R,4S,5R)-5-benzyloxy-3-(fluorenyloxycarbonylamino)-4-hydroxy-2-oxo-1-piperidinyl]isohexanoic acid

Chemical Property of 2(S)-2-[(3R,4S,5R)-5-benzyloxy-3-(fluorenyloxycarbonylamino)-4-hydroxy-2-oxo-1-piperidinyl]isohexanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2(S)-2-[(3R,4S,5R)-5-benzyloxy-3-(fluorenyloxycarbonylamino)-4-hydroxy-2-oxo-1-piperidinyl]isohexanoic acid

There total 3 articles about 2(S)-2-[(3R,4S,5R)-5-benzyloxy-3-(fluorenyloxycarbonylamino)-4-hydroxy-2-oxo-1-piperidinyl]isohexanoic acid 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: 80.0%

(3S,4S,5R)-5-benzyloxy-N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-3-(9-fluorenylmethoxycarbonylamino)-4-hydroxypiperidin-2-one (646057-70-7) → 2(S)-2-[(3R,4S,5R)-5-benzyloxy-3-(fluorenyloxycarbonylamino)-4-hydroxy-2-oxo-1-piperidinyl]isohexanoic acid (646057-74-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2.5h;

DOI:10.1021/jm030943h

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → 2(S)-2-[(3R,4S,5R)-5-benzyloxy-3-(fluorenyloxycarbonylamino)-4-hydroxy-2-oxo-1-piperidinyl]isohexanoic acid (646057-74-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / NaHCO₃ / acetone / 8 h / 20 °C

2: 80 percent / trifluoroacetic acid / CH₂Cl₂ / 2.5 h / 20 °C

With sodium hydrogencarbonate; trifluoroacetic acid; In dichloromethane; acetone;

DOI:10.1021/jm030943h

Reference yield:

(3S,4S,5R)-3-amino-5-benzyloxy-N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-4-hydroxypiperidin-2-one (239784-28-2) → 2(S)-2-[(3R,4S,5R)-5-benzyloxy-3-(fluorenyloxycarbonylamino)-4-hydroxy-2-oxo-1-piperidinyl]isohexanoic acid (646057-74-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / NaHCO₃ / acetone / 8 h / 20 °C

2: 80 percent / trifluoroacetic acid / CH₂Cl₂ / 2.5 h / 20 °C

With sodium hydrogencarbonate; trifluoroacetic acid; In dichloromethane; acetone;

DOI:10.1021/jm030943h

upstream raw materials:

(3S,4S,5R)-5-benzyloxy-N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-3-(9-fluorenylmethoxycarbonylamino)-4-hydroxypiperidin-2-one

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

(3S,4S,5R)-3-amino-5-benzyloxy-N-[(1S)-1-(tert-butoxycarbonyl)-3-methylbutyl]-4-hydroxypiperidin-2-one

Downstream raw materials:

H-Phe-Asn-{Ser(Bn)-Leu}-Ala-Ile-Pro-OH

H-Pro-Phe-Asn-{Ser(Bn)-Leu}-Ala-Ile-OH

benzyl-ψ-stylostatin

epi-benzyl-ψ-stylostatin