(2S,3S,4R)-2-octanamido-1-(1'rs,2'RS,3'SR,4'SR,5'RS,6'SR)-2',3',4',5',6'-pentahydroxycyclohexylaminooctadecane-3,4-diol hydrochloride

Base Information

• Chemical Name: (2S,3S,4R)-2-octanamido-1-(1'rs,2'RS,3'SR,4'SR,5'RS,6'SR)-2',3',4',5',6'-pentahydroxycyclohexylaminooctadecane-3,4-diol hydrochloride
• CAS No.: 1198207-15-6
• Molecular Formula: C₃₂H₆₄N₂O₈*ClH
• Molecular Weight: 641.33
• Mol file: 1198207-15-6.mol

Synonyms:(2S,3S,4R)-2-octanamido-1-(1'rs,2'RS,3'SR,4'SR,5'RS,6'SR)-2',3',4',5',6'-pentahydroxycyclohexylaminooctadecane-3,4-diol hydrochloride

Chemical Property of (2S,3S,4R)-2-octanamido-1-(1'rs,2'RS,3'SR,4'SR,5'RS,6'SR)-2',3',4',5',6'-pentahydroxycyclohexylaminooctadecane-3,4-diol hydrochloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R)-2-octanamido-1-(1'rs,2'RS,3'SR,4'SR,5'RS,6'SR)-2',3',4',5',6'-pentahydroxycyclohexylaminooctadecane-3,4-diol hydrochloride

There total 5 articles about (2S,3S,4R)-2-octanamido-1-(1'rs,2'RS,3'SR,4'SR,5'RS,6'SR)-2',3',4',5',6'-pentahydroxycyclohexylaminooctadecane-3,4-diol hydrochloride 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: 85.0%

(2S,3S,4R)-(3,4-dibenzyloxy-1-(1'rs,2'RS,3'SR,4'SR,5'RS,6'SR)-2',3',4',5',6'-pentabenzyloxycyclohexylaminooctadecan-2-yl)octanamide (1198206-98-2) → (2S,3S,4R)-2-octanamido-1-(1'rs,2'RS,3'SR,4'SR,5'RS,6'SR)-2',3',4',5',6'-pentahydroxycyclohexylaminooctadecane-3,4-diol hydrochloride (1198207-15-6)

Guidance literature:

With boron trichloride; In n-heptane; dichloromethane; at -78 - 20 ℃; for 16h; Inert atmosphere;

Reference yield:

Octanoic acid (124-07-2) → (2S,3S,4R)-2-octanamido-1-(1'rs,2'RS,3'SR,4'SR,5'RS,6'SR)-2',3',4',5',6'-pentahydroxycyclohexylaminooctadecane-3,4-diol hydrochloride (1198207-15-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / tetrahydrofuran / 3 h / Reflux

2: ethyl acetate / 3 h / 20 °C / Reflux

3: sodium tetrahydroborate; acetic acid / dichloromethane; methanol / 18 h / 20 °C / Inert atmosphere

4: boron trichloride / dichloromethane; n-heptane / 16 h / -78 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; boron trichloride; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; n-heptane; dichloromethane; ethyl acetate;

Reference yield:

N-((2S,3S,4R)-3,4-bis(benzyloxy)-1-hydroxyoctadecan-2-yl)octanamide (1198207-19-0) → (2S,3S,4R)-2-octanamido-1-(1'rs,2'RS,3'SR,4'SR,5'RS,6'SR)-2',3',4',5',6'-pentahydroxycyclohexylaminooctadecane-3,4-diol hydrochloride (1198207-15-6)

Guidance literature:

Multi-step reaction with 3 steps

1: ethyl acetate / 3 h / 20 °C / Reflux

2: sodium tetrahydroborate; acetic acid / dichloromethane; methanol / 18 h / 20 °C / Inert atmosphere

3: boron trichloride / dichloromethane; n-heptane / 16 h / -78 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; boron trichloride; acetic acid; In methanol; n-heptane; dichloromethane; ethyl acetate;

upstream raw materials:

Octanoic acid

N-((2S,3S,4R)-3,4-bis(benzyloxy)-1-hydroxyoctadecan-2-yl)octanamide

3,4 di-O-benzylphytosphingosine

(2S,3S,4R)-(3,4-dibenzyloxy-1-(1'rs,2'RS,3'SR,4'SR,5'RS,6'SR)-2',3',4',5',6'-pentabenzyloxycyclohexylaminooctadecan-2-yl)octanamide