3-O-tert-butyldimethylsilyl-1-O-(4-methoxybenzyl)-2-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol

Base Information

• Chemical Name: 3-O-tert-butyldimethylsilyl-1-O-(4-methoxybenzyl)-2-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol
• CAS No.: 637774-37-9
• Molecular Formula: C₂₄H₄₂O₆Si
• Molecular Weight: 454.679
• Mol file: 637774-37-9.mol

Synonyms:3-O-tert-butyldimethylsilyl-1-O-(4-methoxybenzyl)-2-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol

Chemical Property of 3-O-tert-butyldimethylsilyl-1-O-(4-methoxybenzyl)-2-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-tert-butyldimethylsilyl-1-O-(4-methoxybenzyl)-2-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol

There total 5 articles about 3-O-tert-butyldimethylsilyl-1-O-(4-methoxybenzyl)-2-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-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: 56.0%

2-(2-bromoethoxy)tetrahydropyran (17739-45-6,59146-56-4) + 2,3-isopropylidene-glyceraldehyde (15186-48-8) → 3-O-tert-butyldimethylsilyl-1-O-(4-methoxybenzyl)-2-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol (637774-37-9)

Guidance literature:

2,3-isopropylidene-glyceraldehyde; With sodium hydride; In DMF (N,N-dimethyl-formamide); at 20 ℃; for 0.5h;

2-(2-bromoethoxy)tetrahydropyran; With tetra-(n-butyl)ammonium iodide; at 20 ℃; for 18h;

Reference yield: 56.0%

2-(2-bromoethoxy)tetrahydropyran (17739-45-6,59146-56-4) + (R)-1-t-butyldimethylsilyloxy-3-(p-methoxyphenyl)methoxyl-2-propanol (637774-36-8) → 3-O-tert-butyldimethylsilyl-1-O-(4-methoxybenzyl)-2-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol (637774-37-9)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1021/ol0358758

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 3-O-tert-butyldimethylsilyl-1-O-(4-methoxybenzyl)-2-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol (637774-37-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / TEA; DMAP / CH₂Cl₂ / 18 h / 20 °C

2: 56 percent / NaH; tetrabutylammonium iodide / dimethylformamide / 18 h / 20 °C

With dmap; TEA; tetra-(n-butyl)ammonium iodide; sodium hydride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol0358758

upstream raw materials:

2-(2-bromoethoxy)tetrahydropyran

(R)-1-t-butyldimethylsilyloxy-3-(p-methoxyphenyl)methoxyl-2-propanol

tert-butyldimethylsilyl chloride

(S)-3-((4-methoxybenzyl)oxy)propane-1,2-diol

Downstream raw materials:

1-O-(4-methoxybenzyl)-2-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol

Hexadecanoic acid (R)-3-(4-methoxy-benzyloxy)-2-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-propyl ester

1-O-(4-methoxybenzyl)-3-O-oleoyl-2-O-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-sn-glycerol