(2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-hydroxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

Base Information

• Chemical Name: (2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-hydroxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester
• CAS No.: 185208-62-2
• Molecular Formula: C₃₆H₅₇NO₉
• Molecular Weight: 647.85
• Mol file: 185208-62-2.mol

Synonyms:(2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-hydroxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

Chemical Property of (2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-hydroxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-hydroxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

There total 15 articles about (2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-hydroxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl 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: 87.0%

(2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester (178113-67-2) → (2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-hydroxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester (185208-62-2)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1016/0040-4020(96)00951-9

Reference yield:

(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid (178113-66-1) → (2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-hydroxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester (185208-62-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 72 percent / 2,4,6-trichlorobenzoyl chloride; Et₃N; DMAP / ethyl acetate / 2 h

2: 93 percent / H₂ / Pd(OH)2 / ethanol / 2 h

3: 78 percent / 2,4,6-trichlorobenzoyl chloride; Et₃N; DMAP / 6 h / 20 °C

4: 75 percent / HF; pyridine / 3 h / 20 °C

With pyridine; dmap; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; hydrogen; triethylamine; palladium dihydroxide; In ethanol; ethyl acetate; 1: Esterification / 2: Hydrogenolysis / 3: Esterification / 4: Desilylation;

DOI:10.1055/s-1999-2765

Reference yield:

(2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid benzyl ester (185208-61-1) → (2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-hydroxy-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester (185208-62-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / H₂ / Pd(OH)2 / ethanol / 2 h

2: 78 percent / 2,4,6-trichlorobenzoyl chloride; Et₃N; DMAP / 6 h / 20 °C

3: 75 percent / HF; pyridine / 3 h / 20 °C

With pyridine; dmap; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; hydrogen; triethylamine; palladium dihydroxide; In ethanol; 1: Hydrogenolysis / 2: Esterification / 3: Desilylation;

DOI:10.1055/s-1999-2765

upstream raw materials:

(2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-allyloxycarbonyl-2-methyl-propyl ester

n-heptyllithium

L-2-hydroxy-3-methylbutanoic acid allyl ester

benzyl (2S,3R)-3-hydroxy-2-methyldecanoate

Downstream raw materials:

(1R)-1-((1S)-2-{[(1S)-1-carboxy-2-methylpropyl]oxy}-1-methyl-2-oxoethyl)octyl 4-[(tert-butoxycarbonyl)(methyl)amino]-2,4,5-trideoxy-5-phenyl-L-erythro-pentonate

(-)-hapalosin

(1R)-1-((1S)-2-{[(1S)-1-carboxy-2-methylpropyl]oxy}-1-methyl-2-oxoethyl)octyl 2,4,5-trideoxy-4-(methylamino)-5-phenyl-L-erythro-pentonate