(R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5H-furan-2-one

Base Information

• Chemical Name: (R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5H-furan-2-one
• CAS No.: 171595-14-5
• Molecular Formula: C₁₁H₂₀O₃Si
• Molecular Weight: 228.363
• Mol file: 171595-14-5.mol

Synonyms:(R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5H-furan-2-one

Chemical Property of (R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5H-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5H-furan-2-one

There total 1 articles about (R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5H-furan-2-one 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:

(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-hydroxy-dihydro-furan-2-one → (5S)-5-(tert-butyldimethylsilanyloxymethyl)-5H-furan-2-one (105122-15-4) + (R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5H-furan-2-one (171595-14-5)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 ℃; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1002/anie.199727501

Reference yield: 6.0%

methanol (67-56-1) + benzophenone (119-61-9) + (R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5H-furan-2-one (171595-14-5) → (4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-(hydroxy-diphenyl-methyl)-dihydro-furan-2-one + (4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-hydroxymethyl-dihydro-furan-2-one (189160-26-7)

Guidance literature:

Irradiation;

DOI:10.1080/07328319708002533

Reference yield:

(R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-5H-furan-2-one (171595-14-5) → 2,4,6-Triisopropyl-benzenesulfonic acid (5S,6R)-7-(tert-butyl-dimethyl-silanyloxy)-6-(4-methoxy-benzyloxy)-5-[(R)-2-(4-methoxy-benzyloxy)-1-methyl-ethyl]-4-methylene-heptyl ester

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) t-BuLi, 2.) 2-thiophenylCu(CN)Li, 3.) TMSCl, 4.) LHDMS

2: 1.) DIBAL, 2.) NaBH₄ / 1.) toluene, from -78 to -55, 1.5 h, 2.) ethanol, overnight

3: TfOH / diethyl ether / 0.17 h / 0 °C

With sodium tetrahydroborate; chloro-trimethyl-silane; trifluorormethanesulfonic acid; 2-thiophenylCu(CN)Li; tert.-butyl lithium; diisobutylaluminium hydride; lithium hexamethyldisilazane; In diethyl ether;

DOI:10.1021/ja973559g

Downstream raw materials:

(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-hydroxymethyl-dihydro-furan-2-one