1-O-benzyl-2-O-[16-(2-tetrahydropyranyloxy)hexadecanyl]-3-O-[16-(4-methoxybenzyloxy)hexadecanyl]-sn-glycerol

Base Information

Chemical Name:1-O-benzyl-2-O-[16-(2-tetrahydropyranyloxy)hexadecanyl]-3-O-[16-(4-methoxybenzyloxy)hexadecanyl]-sn-glycerol
CAS No.:176211-21-5
Molecular Formula:C₅₅H₉₄O₇
Molecular Weight:867.347
Hs Code.:

Synonyms:1-O-benzyl-2-O-[16-(2-tetrahydropyranyloxy)hexadecanyl]-3-O-[16-(4-methoxybenzyloxy)hexadecanyl]-sn-glycerol

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Chemical Property of 1-O-benzyl-2-O-[16-(2-tetrahydropyranyloxy)hexadecanyl]-3-O-[16-(4-methoxybenzyloxy)hexadecanyl]-sn-glycerol

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Technology Process of 1-O-benzyl-2-O-[16-(2-tetrahydropyranyloxy)hexadecanyl]-3-O-[16-(4-methoxybenzyloxy)hexadecanyl]-sn-glycerol

There total 9 articles about 1-O-benzyl-2-O-[16-(2-tetrahydropyranyloxy)hexadecanyl]-3-O-[16-(4-methoxybenzyloxy)hexadecanyl]-sn-glycerol 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: 97.0%

: 148584-57-0
Methanesulfonic acid 16-(tetrahydro-pyran-2-yloxy)-hexadecyl ester

: 176211-20-4
1-O-benzyl-3-O-[16-(4-methoxybenzyloxy)hexadecanyl]-sn-glycerol

: 176211-21-5
1-O-benzyl-2-O-[16-(2-tetrahydropyranyloxy)hexadecanyl]-3-O-[16-(4-methoxybenzyloxy)hexadecanyl]-sn-glycerol

Guidance literature:: 1-O-benzyl-3-O-[16-(4-methoxybenzyloxy)hexadecanyl]-sn-glycerol; With sodium hydride; In dimethyl sulfoxide; at 20 ℃; for 0.5h;

Methanesulfonic acid 16-(tetrahydro-pyran-2-yloxy)-hexadecyl ester; In dimethyl sulfoxide; at 20 ℃; for 12h;
DOI:10.1246/bcsj.70.2545

Reference yield:

: 139386-65-5
1-hydroxy-16-(2'-tetrahydropyranyloxy)-hexadecane

: 176211-21-5
1-O-benzyl-2-O-[16-(2-tetrahydropyranyloxy)hexadecanyl]-3-O-[16-(4-methoxybenzyloxy)hexadecanyl]-sn-glycerol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 97 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 - 20 °C

2.1: NaH / dimethylsulfoxide / 0.5 h / 20 °C

2.2: 97 percent / dimethylsulfoxide / 12 h / 20 °C

With sodium hydride; triethylamine; In dichloromethane; dimethyl sulfoxide; 1.1: Esterification / 2.1: Metallation / 2.2: Etherification;
DOI:10.1246/bcsj.70.2545

Reference yield:

: 176211-44-2
16-(4-methoxybenzyloxy)-1-hexadecanol

: 176211-21-5
1-O-benzyl-2-O-[16-(2-tetrahydropyranyloxy)hexadecanyl]-3-O-[16-(4-methoxybenzyloxy)hexadecanyl]-sn-glycerol

Guidance literature:: Multi-step reaction with 4 steps

1.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.62 h / -20 °C

1.2: 80 percent / Et₃N / CH₂Cl₂ / -30 - 0 °C

2.1: 97 percent / p-toluenesulfonic acid; MgSO₄ / CH₂Cl₂ / 18 h / 20 °C

3.1: 43 percent / DIBAL-H / toluene / 0 - 20 °C

4.1: NaH / dimethylsulfoxide / 0.5 h / 20 °C

4.2: 97 percent / dimethylsulfoxide / 12 h / 20 °C

With oxalyl dichloride; sodium hydride; diisobutylaluminium hydride; magnesium sulfate; toluene-4-sulfonic acid; dimethyl sulfoxide; In dichloromethane; dimethyl sulfoxide; toluene; 1.1: Swern oxidation / 1.2: Swern oxidation / 2.1: Cyclization / 3.1: Reduction / 4.1: Metallation / 4.2: Etherification;
DOI:10.1246/bcsj.70.2545