(4E,8E,2S,3R,2'R)-N-2'-acetoxyhexadecanoyl-1-O-benzoyl-9-methyl-4,8-sphingadienine

Base Information

• Chemical Name: (4E,8E,2S,3R,2'R)-N-2'-acetoxyhexadecanoyl-1-O-benzoyl-9-methyl-4,8-sphingadienine
• CAS No.: 100924-04-7
• Molecular Formula: C₄₄H₇₃NO₆
• Molecular Weight: 712.067
• Mol file: 100924-04-7.mol

Synonyms:(4E,8E,2S,3R,2'R)-N-2'-acetoxyhexadecanoyl-1-O-benzoyl-9-methyl-4,8-sphingadienine

Chemical Property of (4E,8E,2S,3R,2'R)-N-2'-acetoxyhexadecanoyl-1-O-benzoyl-9-methyl-4,8-sphingadienine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4E,8E,2S,3R,2'R)-N-2'-acetoxyhexadecanoyl-1-O-benzoyl-9-methyl-4,8-sphingadienine

There total 15 articles about (4E,8E,2S,3R,2'R)-N-2'-acetoxyhexadecanoyl-1-O-benzoyl-9-methyl-4,8-sphingadienine 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:

(E)-4-methyl-3-tridecene-1-tosylate (95603-75-1) → (4E,8E,2S,3R,2'R)-N-2'-acetoxyhexadecanoyl-1-O-benzoyl-9-methyl-4,8-sphingadienine (100924-04-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 93.4 percent / LiBr / dimethylformamide / 18 h / Ambient temperature

2: 98 percent / dimethylformamide; H₂O / 24 h / 70 °C

3: 95.4 percent / 1.7M DIBAL-H / hexane; diethyl ether / 1.) -60 deg C, 1h, 2.) rt., 3 h

4: 77.6 percent / Ph₃P / CH₂Cl₂ / 0.25 h / 0 °C

5: 88 percent / 1.5M n-BuLi / hexane; tetrahydrofuran / 1 h / -70 °C / 1.) -70 deg C, 1h, 2.) room temperature, 1.5 h

6: 1.) 1.7M DIBAL-H / 1.) hexane, 50 deg C, 2 h; 2.) ether, room temperature, 2 h

7: 2 N HCl / tetrahydrofuran / 20 h / Ambient temperature

8: pyridine / 20 h / 45 °C

With hydrogenchloride; n-butyllithium; diisobutylaluminium hydride; triphenylphosphine; lithium bromide; In tetrahydrofuran; pyridine; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)96633-5

Reference yield:

(E)-4-methyl-3-tridecen-1-ol (95603-74-0) → (4E,8E,2S,3R,2'R)-N-2'-acetoxyhexadecanoyl-1-O-benzoyl-9-methyl-4,8-sphingadienine (100924-04-7)

Guidance literature:

Multi-step reaction with 9 steps

1: pyridine / 8 h

2: 93.4 percent / LiBr / dimethylformamide / 18 h / Ambient temperature

3: 98 percent / dimethylformamide; H₂O / 24 h / 70 °C

4: 95.4 percent / 1.7M DIBAL-H / hexane; diethyl ether / 1.) -60 deg C, 1h, 2.) rt., 3 h

5: 77.6 percent / Ph₃P / CH₂Cl₂ / 0.25 h / 0 °C

6: 88 percent / 1.5M n-BuLi / hexane; tetrahydrofuran / 1 h / -70 °C / 1.) -70 deg C, 1h, 2.) room temperature, 1.5 h

7: 1.) 1.7M DIBAL-H / 1.) hexane, 50 deg C, 2 h; 2.) ether, room temperature, 2 h

8: 2 N HCl / tetrahydrofuran / 20 h / Ambient temperature

9: pyridine / 20 h / 45 °C

With hydrogenchloride; n-butyllithium; diisobutylaluminium hydride; triphenylphosphine; lithium bromide; In tetrahydrofuran; pyridine; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)96633-5

Reference yield:

(E)-1-bromo-4-methyl-3-tridecene (100923-94-2) → (4E,8E,2S,3R,2'R)-N-2'-acetoxyhexadecanoyl-1-O-benzoyl-9-methyl-4,8-sphingadienine (100924-04-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 98 percent / dimethylformamide; H₂O / 24 h / 70 °C

2: 95.4 percent / 1.7M DIBAL-H / hexane; diethyl ether / 1.) -60 deg C, 1h, 2.) rt., 3 h

3: 77.6 percent / Ph₃P / CH₂Cl₂ / 0.25 h / 0 °C

4: 88 percent / 1.5M n-BuLi / hexane; tetrahydrofuran / 1 h / -70 °C / 1.) -70 deg C, 1h, 2.) room temperature, 1.5 h

5: 1.) 1.7M DIBAL-H / 1.) hexane, 50 deg C, 2 h; 2.) ether, room temperature, 2 h

6: 2 N HCl / tetrahydrofuran / 20 h / Ambient temperature

7: pyridine / 20 h / 45 °C

With hydrogenchloride; n-butyllithium; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; pyridine; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)96633-5

upstream raw materials:

p-nitrophenyl 2-O-acetyl-(2R)-2-hydroxypalmitate

1-O-benzoylsphingadienine*HCl

(R)-(-)-2-hydroxyhexadecanoic acid

methyl (R)-2-hydroxyhexadecanoate

Downstream raw materials:

(4E,8E,2S,3R,2'R)-N-2'-hydroxyhexadecanoyl-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine

(4E,8E,2S,3R,2'R)-N-2'-hydroxyhexadecanoyl-1-O-β-D-glucopyranosyl-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine

(4E,8E,2S,3R,2'R)-N-2'-hydroxyhexadecanoyl-1-O-(tetra-O-acetyl-β-D-glucopyranosyl)-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine

1-O-(β-D-glucopyranosyl)-(2S,3R,4E,8E)-2-[(2'R)-2'-(hydroxyhexadecanoyl)amido]-9-methyl-4,8-octadecadiene-1,3-diol

Refernces