1-octadecanoyl-2-[7-(tert-butyldiphenylsilyloxy)hept-5(Z)-enoyl]-sn-glycero-3-phosphocholine

Base Information

• Chemical Name: 1-octadecanoyl-2-[7-(tert-butyldiphenylsilyloxy)hept-5(Z)-enoyl]-sn-glycero-3-phosphocholine
• CAS No.: 264874-81-9
• Molecular Formula: C₄₉H₈₂NO₉PSi
• Molecular Weight: 888.251

Synonyms:1-octadecanoyl-2-[7-(tert-butyldiphenylsilyloxy)hept-5(Z)-enoyl]-sn-glycero-3-phosphocholine

Chemical Property of 1-octadecanoyl-2-[7-(tert-butyldiphenylsilyloxy)hept-5(Z)-enoyl]-sn-glycero-3-phosphocholine

Chemical Property:

Purity/Quality:

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Technology Process of 1-octadecanoyl-2-[7-(tert-butyldiphenylsilyloxy)hept-5(Z)-enoyl]-sn-glycero-3-phosphocholine

There total 6 articles about 1-octadecanoyl-2-[7-(tert-butyldiphenylsilyloxy)hept-5(Z)-enoyl]-sn-glycero-3-phosphocholine 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: 35.0%

1-stearoyl-sn-glycero-3-phosphocholine (19420-57-6,5655-17-4) + 7-(tert-butyldiphenylsilyloxy)hept-5(Z)-enoic acid (264874-80-8) → 1-octadecanoyl-2-[7-(tert-butyldiphenylsilyloxy)hept-5(Z)-enoyl]-sn-glycero-3-phosphocholine (264874-81-9)

Guidance literature:

With 4-(Methylamino)pyridine; dicyclohexyl-carbodiimide; In chloroform; at 20 ℃; for 48h;

DOI:10.1002/(SICI)1096-9888(200002)35:2<224::AID-JMS933>3.0.CO;2-G

Reference yield:

methyl 7-hydroxy-5-heptynoate (50781-91-4) → 1-octadecanoyl-2-[7-(tert-butyldiphenylsilyloxy)hept-5(Z)-enoyl]-sn-glycero-3-phosphocholine (264874-81-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / NaBH₄; H₂; ethylenediamine / Ni(OAc)2 / aq. ethanol / 3 h

2: 86 percent / N,N-dimethylaminopyridine; pyridine / CH₂Cl₂ / 6 h

3: 98 percent / aq. LiOH / tetrahydrofuran / 12 h / 20 °C

4: 35 percent / 1,3-dicyclohexylcarbodiimide; 4-methylaminopyridine / CHCl₃ / 48 h / 20 °C

With pyridine; 4-(Methylamino)pyridine; dmap; lithium hydroxide; sodium tetrahydroborate; hydrogen; ethylenediamine; dicyclohexyl-carbodiimide; nickel diacetate; In tetrahydrofuran; ethanol; dichloromethane; chloroform; 1: Reduction / 2: silylation / 3: Hydrolysis / 4: Esterification;

DOI:10.1002/(SICI)1096-9888(200002)35:2<224::AID-JMS933>3.0.CO;2-G

Reference yield:

hex-5-ynoic acid (53293-00-8) → 1-octadecanoyl-2-[7-(tert-butyldiphenylsilyloxy)hept-5(Z)-enoyl]-sn-glycero-3-phosphocholine (264874-81-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -40 °C

1.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / 20 °C

2.1: diethyl ether

3.1: 96 percent / NaBH₄; H₂; ethylenediamine / Ni(OAc)2 / aq. ethanol / 3 h

4.1: 86 percent / N,N-dimethylaminopyridine; pyridine / CH₂Cl₂ / 6 h

5.1: 98 percent / aq. LiOH / tetrahydrofuran / 12 h / 20 °C

6.1: 35 percent / 1,3-dicyclohexylcarbodiimide; 4-methylaminopyridine / CHCl₃ / 48 h / 20 °C

With pyridine; 4-(Methylamino)pyridine; dmap; lithium hydroxide; sodium tetrahydroborate; n-butyllithium; hydrogen; ethylenediamine; dicyclohexyl-carbodiimide; nickel diacetate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; chloroform; 1.1: Metallation / 1.2: Addition / 2.1: Methylation / 3.1: Reduction / 4.1: silylation / 5.1: Hydrolysis / 6.1: Esterification;

DOI:10.1002/(SICI)1096-9888(200002)35:2<224::AID-JMS933>3.0.CO;2-G

upstream raw materials:

1-stearoyl-sn-glycero-3-phosphocholine

7-(tert-butyldiphenylsilyloxy)hept-5(Z)-enoic acid

hex-5-ynoic acid

7-Hydroxy-5-heptynoic Acid

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