(3S,4R,5S)-4-benzyloxycarbonylamino-3-hydroxy-5-methyl-heptanoic acid methyl ester

Base Information

• Chemical Name: (3S,4R,5S)-4-benzyloxycarbonylamino-3-hydroxy-5-methyl-heptanoic acid methyl ester
• CAS No.: 159407-39-3
• Molecular Formula: C₁₇H₂₅NO₅
• Molecular Weight: 323.389
• Mol file: 159407-39-3.mol

Synonyms:(3S,4R,5S)-4-benzyloxycarbonylamino-3-hydroxy-5-methyl-heptanoic acid methyl ester

Chemical Property of (3S,4R,5S)-4-benzyloxycarbonylamino-3-hydroxy-5-methyl-heptanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,5S)-4-benzyloxycarbonylamino-3-hydroxy-5-methyl-heptanoic acid methyl ester

There total 15 articles about (3S,4R,5S)-4-benzyloxycarbonylamino-3-hydroxy-5-methyl-heptanoic acid methyl 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%

(4R,5S)-4-benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid methyl ester (159360-04-0) → (3S,4R,5S)-4-benzyloxycarbonylamino-3-hydroxy-5-methyl-heptanoic acid methyl ester (159407-39-3)

Guidance literature:

With potassium borohydride; In methanol; at -30 - 0 ℃;

DOI:10.1021/ja010222c

Reference yield:

(2R,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoic acid pentafluorophenyl ester (250039-48-6) → (3S,4R,5S)-4-benzyloxycarbonylamino-3-hydroxy-5-methyl-heptanoic acid methyl ester (159407-39-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium diisopropylamide / tetrahydrofuran / 1 h / -78 °C

1.2: 3.42 g / tetrahydrofuran / 0.75 h / -78 °C

2.1: potassium borohydride / methanol / 0.83 h / -78 - 0 °C

With potassium borohydride; lithium diisopropyl amide; In tetrahydrofuran; methanol;

DOI:10.1021/ol9910058

Reference yield:

N-(benzyloxycarbonyl)succinimide (75315-63-8) → (3S,4R,5S)-4-benzyloxycarbonylamino-3-hydroxy-5-methyl-heptanoic acid methyl ester (159407-39-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / Et₃N / CH₂Cl₂ / 0 - 20 °C

2: EDAC*HCl; DMAP / CH₂Cl₂ / 4.5 h / 0 - 20 °C

3: 3.42 g / tetrahydrofuran / 0.75 h / -78 °C

4: potassium borohydride / methanol / 0.83 h / -78 - 0 °C

With dmap; potassium borohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja010222c

upstream raw materials:

(4R,5S)-4-benzyloxycarbonylamino-5-methyl-3-oxo-heptanoic acid methyl ester

N-(Benzyloxycarbonyloxy)succinimide

(2R,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoic acid pentafluorophenyl ester

N-(benzyloxycarbonyl)succinimide

Downstream raw materials:

C₆₇H₁₁₁N₅O₁₆Si₂

N-Z-prolyl-[Hiv²] didemnin A

C₆₁H₉₇N₅O₁₅Si

4-amino-5-methyl-3-triisopropylsilanyloxy-heptanoic acid 1-[1-(2-{[1-(2-tert-butoxycarbonylamino-2-carboxy-1-methyl-ethoxycarbonyl)-2-(4-methoxy-phenyl)-ethyl]-methyl-carbamoyl}-pyrrolidine-1-carbonyl)-3-methyl-butylcarbamoyl]-2-methyl-propyl ester