Hexanal, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-6-(phenylmethoxy)-, (2R,3S)-

Base Information

• Chemical Name: Hexanal, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-6-(phenylmethoxy)-, (2R,3S)-
• CAS No.: 192370-73-3
• Molecular Formula: C20H34O3Si
• Molecular Weight: 350.574
• Mol file: 192370-73-3.mol

Synonyms:

Chemical Property of Hexanal, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-6-(phenylmethoxy)-, (2R,3S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Hexanal, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-6-(phenylmethoxy)-, (2R,3S)-

There total 11 articles about Hexanal, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methyl-6-(phenylmethoxy)-, (2R,3S)- 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: 82.0%

[(1S,2S)-1-(3-Benzyloxy-propyl)-2-methyl-but-3-enyloxy]-tert-butyl-dimethyl-silane (192370-72-2) → (2R,3S)-6-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylhexanal (192370-73-3)

Guidance literature:

With 2,3-dimercapto-succinic acid; ozone; In methanol; dichloromethane; at -78 ℃;

DOI:10.1016/S0040-4039(97)00931-3

Reference yield: 15.0%

t-butyldimethylsiyl triflate (69739-34-0) + ((2S,3S)-3-(3-(benzyloxy)propyl)-2-methyloxiran-2-yl)methanol → (2R,3S)-6-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylhexanal (192370-73-3)

Guidance literature:

((2S,3S)-3-(3-(benzyloxy)propyl)-2-methyloxiran-2-yl)methanol; With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.333333h; Molecular sieve;

t-butyldimethylsiyl triflate; In dichloromethane; at -42 ℃; Molecular sieve;

DOI:10.1016/j.tetlet.2013.01.134

Reference yield:

4-benzyloxybutanal (5470-84-8) → (2R,3S)-6-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-2-methylhexanal (192370-73-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.) aq. NaOH, H₂O₂ / 1.) Et₂O, -78 deg C

2: 2,6-lutidine / CH₂Cl₂

3: 82 percent / O₃; DMS / CH₂Cl₂; methanol / -78 °C

With 2,6-dimethylpyridine; sodium hydroxide; 2,3-dimercapto-succinic acid; dihydrogen peroxide; ozone; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(97)00931-3

upstream raw materials:

[(1S,2S)-1-(3-Benzyloxy-propyl)-2-methyl-but-3-enyloxy]-tert-butyl-dimethyl-silane

4-benzyloxybutanal

t-butyldimethylsiyl triflate

(3S,4S)-7-(benzyloxy)-3-methylhept-1-en-4-ol

Downstream raw materials:

(4S,5S,E)-ethyl 8-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4-methyloct-2-enoate

ethyl 2-((2R,3S,5S,6S)-6-(3-(benzyloxy)propyl)-3-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)acetate

(4S,5S)-8-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4-methyloctanal

(4S,6S,7S,E)-ethy 10-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-4-hydroxy-6-methyldec-2-enoate

Refernces

• 1、 Sabitha, Gowravaram,Nayak, Sambit,Bhikshapathi,Yadav. "Palladium hydroxide catalyzed isomerization of primary allylic alcohols to aldehydes: Application to the formal synthesis of (-)-brevisamide". . p. 382 - 385. Retrieved 2011/04/15.
• 2、 Balog, Aaron,Bertinato, Peter,Su, Dai-Shi,Meng, Dongfang,Sorensen, Erik,Danishefsky, Samuel J.,Zheng, Yu-Huang,Chou, Ting-Chao,He, Lifeng,Horwitz, Susan B.. "Stereoselective syntheses and evaluation of compounds in the 8-desmethylepothilone a series: Some surprising observations regarding their chemical and biological properties". . p. 4529 - 4532. Retrieved 2007/10/03.