(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

Base Information

• Chemical Name: (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
• CAS No.: 185208-63-3
• Molecular Formula: C₂₈H₄₅NO₇
• Molecular Weight: 507.668
• Mol file: 185208-63-3.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 31 articles about (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 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: 94.0%

(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 (238753-91-8) → (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 (185208-63-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 2h; Ambient temperature;

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

Reference yield: 94.0%

(2S,3R)-3-[(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoyloxy]-2-methyl-decanoic acid (S)-1-carboxy-2-methyl-propyl ester → (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 (185208-63-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane;

DOI:10.1016/0040-4039(96)00592-8

Reference yield:

(3R,4S)-4-(tert-Butoxycarbonyl-methyl-amino)-3-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-pentanoic acid (178113-66-1) → (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 (185208-63-3)

Guidance literature:

Multi-step reaction with 6 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

5: 92 percent / morpholine / (Ph₃P)4Pd / tetrahydrofuran / 2 h / 20 °C

6: 87 percent / TFA / CH₂Cl₂ / 2 h / 20 °C

With morpholine; pyridine; dmap; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; hydrogen; triethylamine; trifluoroacetic acid; palladium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; 1: Esterification / 2: Hydrogenolysis / 3: Esterification / 4: Desilylation / 5: Deallylation / 6: Deacylation;

DOI:10.1055/s-1999-2765

upstream 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

Octanal

(2S,3R)-2-methyl-3-(tetrahydro-2H-pyran-2-yloxy)decanoic acid

(2S,3R)-[(S)-1-(benzyloxy)-3-methyl-1-oxobutan-2-yl]-3-hydroxy-2-methyldecanoate

Downstream raw materials:

(-)-hapalosin

Refernces

• 1、 Haddad, Mansour,Botuha, Candice,Larchevêque, Marc. "Total synthesis of the multidrug-resistance reversing agent hapalosin". . p. 1118 - 1120. Retrieved 2007/10/03.
• 2、 Okuno, Toshiaki,Ohmori, Ken,Nishiyama, Shigeru,Yamamura, Shosuke,Nakamura, Kensuke,Houk,Okamoto, Kazuya. "Chemical study on hapalosin, a cyclic depsipeptide possessing multidrug resistance reversing activities: Synthesis, structure and biological activity". . p. 14723 - 14734. Retrieved 2007/10/03.