methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3R,4R,5R)-tetrahydro-2-furanyl]-(Z)-2-propenoate

Base Information

• Chemical Name: methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3R,4R,5R)-tetrahydro-2-furanyl]-(Z)-2-propenoate
• CAS No.: 869733-55-1
• Molecular Formula: C₂₆H₄₄O₅Si₂
• Molecular Weight: 492.803
• Mol file: 869733-55-1.mol

Synonyms:methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3R,4R,5R)-tetrahydro-2-furanyl]-(Z)-2-propenoate

Chemical Property of methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3R,4R,5R)-tetrahydro-2-furanyl]-(Z)-2-propenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3R,4R,5R)-tetrahydro-2-furanyl]-(Z)-2-propenoate

There total 5 articles about methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3R,4R,5R)-tetrahydro-2-furanyl]-(Z)-2-propenoate 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: 85.0%

(2R,3R,4R,5R)-3,4-bis(tert-butyldimethylsiloxy)-5-phenyltetrahydrofuran-2-carbaldehyde (1002753-33-4) + bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (88738-78-7) → methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3R,4R,5R)-tetrahydro-2-furanyl]-(Z)-2-propenoate (869733-55-1)

Guidance literature:

With 18-crown-6 ether; potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 3h;

DOI:10.1016/j.bmc.2009.11.045

Reference yield:

ethyl 3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2R,3R,4R,5R)-tetrahydro-2-furancarboxylate (869733-51-7) → methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3R,4R,5R)-tetrahydro-2-furanyl]-(Z)-2-propenoate (869733-55-1)

Guidance literature:

Multi-step reaction with 2 steps

1: DIBAL-H / CH₂Cl₂; hexane / -78 °C

2: methanol / 20 °C

With diisobutylaluminium hydride; In methanol; hexane; dichloromethane; 2: Wittig olefination;

DOI:10.1016/j.tetasy.2005.08.047

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3R,4R,5R)-tetrahydro-2-furanyl]-(Z)-2-propenoate (869733-55-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / imidazole / CH₂Cl₂ / 4 h / 0 - 20 °C

2: DIBAL-H / CH₂Cl₂; hexane / -78 °C

3: methanol / 20 °C

With 1H-imidazole; diisobutylaluminium hydride; In methanol; hexane; dichloromethane; 3: Wittig olefination;

DOI:10.1016/j.tetasy.2005.08.047

upstream raw materials:

(2R,3R,4R,5R)-3,4-bis(tert-butyldimethylsiloxy)-5-phenyltetrahydrofuran-2-carbaldehyde

methyl (triphenylphosphoranylidene)acetate

ethyl 3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2R,3R,4R,5R)-tetrahydro-2-furancarboxylate

tert-butyldimethylsilyl chloride

Downstream raw materials:

methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3R,4R,5R)-tetrahydro-2-furanyl]-propanoate

goniothalenol

methyl 3-([2S,3S,4R,5R]-3,4-dihydroxy-5-phenyltetrahydrofuran-2-yl)propionate