hapalosin

Base Information

• Chemical Name: hapalosin
• CAS No.: 159542-04-8
• Molecular Formula: C₂₈H₄₃NO₆
• Molecular Weight: 489.653
• Mol file: 159542-04-8.mol

Synonyms:1,9-Dioxa-4-azacyclododecane-3,8,12-trione,10-heptyl-6-hydroxy-4,11-dimethyl-2-(1-methylethyl)-5-(phenylmethyl)-,[2S-(2R*,5R*,6S*,10S*,11R*)]-; Hapalosin

Chemical Property of hapalosin

Chemical Property:

• Vapor Pressure: 6.06E-20mmHg at 25°C
• Boiling Point: 689.2°Cat760mmHg
• PKA: 13.48±0.70(Predicted)
• Flash Point: 370.6°C
• PSA: 93.14000
• Density: 1.057g/cm³
• LogP: 4.23480

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of hapalosin

There total 133 articles about hapalosin 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: 44.0%

(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) → (-)-hapalosin (159542-04-8)

Guidance literature:

With diphenyl-phosphinic acid; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide;

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

Reference yield: 41.0%

C35H51NO7 → (-)-hapalosin (159542-04-8)

Guidance literature:

C₃₅H₅₁NO₇; With palladium 10% on activated carbon; hydrogen; In ethanol; for 6h;

With diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine; In ethanol; N,N-dimethyl-formamide; at 0 - 20 ℃; for 101h;

DOI:10.1039/c6ob02523d

Reference yield: 32.0%

(2S,3R)-3-((3R,4S)-3-Hydroxy-4-methylamino-5-phenyl-pentanoyloxy)-2-methyl-decanoic acid (S)-1-carboxy-2-methyl-propyl ester; compound with trifluoro-acetic acid → (-)-hapalosin (159542-04-8)

Guidance literature:

With diphenyl-phosphinic acid; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 ℃; for 72h;

upstream raw materials:

(2S,3R)-3-Hydroxy-2-methyl-decanoic acid (S)-1-{[(1S,2R)-1-benzyl-2-(tert-butyl-dimethyl-silanyloxy)-3-carboxy-propyl]-methyl-carbamoyl}-2-methyl-propyl ester

(2S,5S,6R,10R,11S)-5-Benzyl-10-heptyl-2-isopropyl-6-methoxymethoxy-4,11-dimethyl-1,9-dioxa-4-aza-cyclododecane-3,8,12-trione

(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

(2S,5S,6R,10R,11S)-5-Benzyl-6-(tert-butyl-dimethyl-silanyloxy)-10-heptyl-2-isopropyl-4,11-dimethyl-1,9-dioxa-4-aza-cyclododecane-3,8,12-trione

Refernces

• 1、 Palomo, Claudio,Oiarbide, Mikel,Garcia, Jesus M.,Gonzalez, Alberto,Pazos, Raquel,Odriozola, Jose M.,Banuelos, Patricia,Tello, Monica,Linden, Anthony. "A practical total synthesis of hapalosin, a 12-membered cyclic depsipeptide with multidrug resistance-reversing activity, by employing improved segment coupling and macrolactonization". . p. 4126 - 4134. Retrieved 2007/10/03.
• 2、 Hermann, Christoph,Pais, Godwin C.G,Geyer, Armin,Kühnert, Sven M,Maier, Martin E. "Total synthesis of hapalosin and two ring expanded analogs". . p. 8461 - 8471. Retrieved 2007/10/03.