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

Base Information

• Chemical Name: methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3R,4R,5R)-tetrahydro-2-furanyl]-propanoate
• CAS No.: 869733-37-9
• Molecular Formula: C₂₆H₄₆O₅Si₂
• Molecular Weight: 494.819
• Mol file: 869733-37-9.mol

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

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

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]-propanoate

There total 6 articles about methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3R,4R,5R)-tetrahydro-2-furanyl]-propanoate 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: 94.0%

methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3R,4R,5R)-tetrahydro-2-furanyl]-(Z)-2-propenoate (869733-55-1) → methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3R,4R,5R)-tetrahydro-2-furanyl]-propanoate (869733-37-9)

Guidance literature:

With formic acid; hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 3h;

DOI:10.1016/j.tetasy.2005.08.047

Reference yield: 66.0%

(2S,3S,4S,5R)-2-(but-3-enyl)-3,4-bis-tert-butyldimethylsilyloxy-tetrahydro-5-phenylfuran (887927-64-2) + methanol (67-56-1) → methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3R,4R,5R)-tetrahydro-2-furanyl]-propanoate (869733-37-9) + 3-[(2S,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-phenyl-tetrahydro-furan-2-yl]-propionaldehyde

Guidance literature:

(2S,3S,4S,5R)-2-(but-3-enyl)-3,4-bis-tert-butyldimethylsilyloxy-tetrahydro-5-phenylfuran; methanol; With sodium hydrogencarbonate; ozone; In dichloromethane; at -70 ℃;

With dmap; acetic anhydride; triethylamine; In benzene; for 4h; Heating;

DOI:10.1021/jo060159f

Reference yield:

(2R,3R,4R,5R)-3,4-bis(tert-butyldimethylsiloxy)-5-phenyltetrahydrofuran-2-carbaldehyde (1002753-33-4) → methyl 3-[3,4-di-tert-butyldimethylsilanyloxy-5-phenyl-(2S,3R,4R,5R)-tetrahydro-2-furanyl]-propanoate (869733-37-9)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol / 20 °C

2: 94 percent / hydrogen; formic acid / palladium on carbon / methanol / 3 h / 20 °C

With formic acid; hydrogen; palladium on activated charcoal; In methanol; 1: Wittig olefination;

DOI:10.1016/j.tetasy.2005.08.047

upstream raw materials:

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

(2S,3S,4S,5R)-2-(but-3-enyl)-3,4-bis-tert-butyldimethylsilyloxy-tetrahydro-5-phenylfuran

methanol

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

Downstream raw materials:

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