benzyl (S)-14-(tert-butyldimethylsiloxy)-2-hydroxytetradecanoate

Base Information

• Chemical Name: benzyl (S)-14-(tert-butyldimethylsiloxy)-2-hydroxytetradecanoate
• CAS No.: 1244784-71-1
• Molecular Formula: C₂₇H₄₈O₄Si
• Molecular Weight: 464.761
• Mol file: 1244784-71-1.mol

Synonyms:benzyl (S)-14-(tert-butyldimethylsiloxy)-2-hydroxytetradecanoate

Chemical Property of benzyl (S)-14-(tert-butyldimethylsiloxy)-2-hydroxytetradecanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (S)-14-(tert-butyldimethylsiloxy)-2-hydroxytetradecanoate

There total 2 articles about benzyl (S)-14-(tert-butyldimethylsiloxy)-2-hydroxytetradecanoate 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: 51.0%

diphenylacetic anhydride (1760-46-9) + benzyl 14-(tert-butyldimethylsiloxy)-2-hydroxytetradecanoate (1244784-67-5) → benzyl (S)-14-(tert-butyldimethylsiloxy)-2-hydroxytetradecanoate (1244784-71-1) + benzyl (R)-14-(tert-butyldimethylsiloxy)-2-(diphenylacetyloxy)tetradecanoate (1244784-72-2)

Guidance literature:

With (R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; 2,2-dimethylpropanoic anhydride; N-ethyl-N,N-diisopropylamine; In diethyl ether; at 20 ℃; for 12h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.08.018

Reference yield: 48.0%

2,2-diphenylacetic acid (117-34-0) + benzyl 14-(tert-butyldimethylsiloxy)-2-hydroxytetradecanoate (1244784-67-5) → benzyl (S)-14-(tert-butyldimethylsiloxy)-2-hydroxytetradecanoate (1244784-71-1) + benzyl (R)-14-(tert-butyldimethylsiloxy)-2-(diphenylacetyloxy)tetradecanoate (1244784-72-2)

Guidance literature:

With 2,2-dimethylpropanoic anhydride; N-ethyl-N,N-diisopropylamine; (R)-(+)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; In diethyl ether; at 20 ℃; for 12h; Product distribution / selectivity;

Reference yield: 33.0%

benzyl (S)-14-(tert-butyldimethylsiloxy)-2-hydroxytetradecanoate (1244784-71-1) + O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → C35H56O5Si (1244784-74-4)

Guidance literature:

camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 16h;

upstream raw materials:

diphenylacetic anhydride

benzyl 14-(tert-butyldimethylsiloxy)-2-hydroxytetradecanoate

2,2-diphenylacetic acid

Downstream raw materials:

C₃₅H₅₆O₅Si

C₂₈H₅₂O₄Si

(2S)-14-(t-butyldimethylsiloxy)-1-(t-butyldiphenylsiloxy)-2-(p-methoxybenzyloxy)tetradecane

(13S)-14-(t-butyldiphenylsiloxy)-13-(p-methoxybenzyloxy)tetradecanol