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

Base Information

• Chemical Name: (4E,8E,2S,3R,2'R)-N-2'-hydroxyhexadecanoyl-1-O-β-D-glucopyranosyl-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine
• CAS No.: 100924-07-0
• Molecular Formula: C₅₇H₉₅NO₉Si
• Molecular Weight: 966.468
• Mol file: 100924-07-0.mol

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

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

There total 18 articles about (4E,8E,2S,3R,2'R)-N-2'-hydroxyhexadecanoyl-1-O-β-D-glucopyranosyl-3-O-(t-butyldiphenylsilyl)-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: 83.2%

(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 (100933-63-9) → (4E,8E,2S,3R,2'R)-N-2'-hydroxyhexadecanoyl-1-O-β-D-glucopyranosyl-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine (100924-07-0)

Guidance literature:

With sodium hydroxide; In methanol; chloroform; for 0.333333h; Ambient temperature;

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'-hydroxyhexadecanoyl-1-O-β-D-glucopyranosyl-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine (100924-07-0)

Guidance literature:

Multi-step reaction with 13 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

10: 89.5 percent / imidazole / dimethylformamide / 3 h / 70 °C

11: 91.9 percent / 0.2N NaOH / methanol; CHCl₃ / 0.25 h / Ambient temperature

12: 47.2 percent / Hg(CN)2 / nitromethane; benzene / 3.5 h / 80 °C

13: 83.2 percent / 0.5N NaOH / methanol; CHCl₃ / 0.33 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; sodium hydroxide; n-butyllithium; mercury(II) cyanide; diisobutylaluminium hydride; triphenylphosphine; lithium bromide; In tetrahydrofuran; pyridine; methanol; diethyl ether; nitromethane; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; benzene;

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

Reference yield:

(E)-4-methyl-3-tridecene-1-tosylate (95603-75-1) → (4E,8E,2S,3R,2'R)-N-2'-hydroxyhexadecanoyl-1-O-β-D-glucopyranosyl-3-O-(t-butyldiphenylsilyl)-9-methyl-4,8-sphingadienine (100924-07-0)

Guidance literature:

Multi-step reaction with 12 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

9: 89.5 percent / imidazole / dimethylformamide / 3 h / 70 °C

10: 91.9 percent / 0.2N NaOH / methanol; CHCl₃ / 0.25 h / Ambient temperature

11: 47.2 percent / Hg(CN)2 / nitromethane; benzene / 3.5 h / 80 °C

12: 83.2 percent / 0.5N NaOH / methanol; CHCl₃ / 0.33 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; sodium hydroxide; n-butyllithium; mercury(II) cyanide; diisobutylaluminium hydride; triphenylphosphine; lithium bromide; In tetrahydrofuran; pyridine; methanol; diethyl ether; nitromethane; hexane; dichloromethane; chloroform; water; N,N-dimethyl-formamide; benzene;

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

upstream raw materials:

(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

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

methyl (R)-2-hydroxyhexadecanoate

D(R)-α-acetoxypalmitic acid

Downstream raw materials:

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