(2S,3R,4R)-4-(tert-butyldimethylsilanyloxy)-3-(4-methoxy-benzyloxy)-2,5-dimethyl-5-hexenal

Base Information

Chemical Name:(2S,3R,4R)-4-(tert-butyldimethylsilanyloxy)-3-(4-methoxy-benzyloxy)-2,5-dimethyl-5-hexenal
CAS No.:228419-58-7
Molecular Formula:C₂₂H₃₆O₄Si
Molecular Weight:392.611
Hs Code.:

Synonyms:(2S,3R,4R)-4-(tert-butyldimethylsilanyloxy)-3-(4-methoxy-benzyloxy)-2,5-dimethyl-5-hexenal

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Chemical Property of (2S,3R,4R)-4-(tert-butyldimethylsilanyloxy)-3-(4-methoxy-benzyloxy)-2,5-dimethyl-5-hexenal

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Technology Process of (2S,3R,4R)-4-(tert-butyldimethylsilanyloxy)-3-(4-methoxy-benzyloxy)-2,5-dimethyl-5-hexenal

There total 5 articles about (2S,3R,4R)-4-(tert-butyldimethylsilanyloxy)-3-(4-methoxy-benzyloxy)-2,5-dimethyl-5-hexenal 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:

: 319922-89-9
(2R,3R,4R)-4-(tert-butyldimethylsilanyloxy)-3-(4-methoxy-benzyloxy)-2,5-dimethyl-hex-en-1-ol

: 228419-58-7
(2S,3R,4R)-4-(tert-butyldimethylsilanyloxy)-3-(4-methoxy-benzyloxy)-2,5-dimethyl-5-hexenal

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.25h;
DOI:10.1021/jo001236o

Reference yield:

: 160238-46-0
(2R)-3-(4-methoxybenzyloxy)-2-methyl-1-propanal

: 228419-58-7
(2S,3R,4R)-4-(tert-butyldimethylsilanyloxy)-3-(4-methoxy-benzyloxy)-2,5-dimethyl-5-hexenal

Guidance literature:: Multi-step reaction with 4 steps

1.1: MgBr₂*Et₂O / CH₂Cl₂ / 0.5 h / -25 °C

1.2: 93 percent / CH₂Cl₂ / -25 - 23 °C

2.1: 79 percent / DDQ; 3 Angstroem molecular sieves / CH₂Cl₂ / 3.5 h

3.1: 77 percent / DIBAL / CH₂Cl₂ / 4 h / -78 - -20 °C

4.1: (COCl)2; DMSO / CH₂Cl₂ / 0.25 h / -78 °C

With oxalyl dichloride; 3 A molecular sieve; diisobutylaluminium hydride; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; magnesium bromide; In dichloromethane; 4.1: Swern oxidation;
DOI:10.1021/jo001236o

Reference yield:

: 228419-55-4
(Z)-γ-(tert-butyldimethylsilanyloxy)methallyltributylstannane

: 228419-58-7
(2S,3R,4R)-4-(tert-butyldimethylsilanyloxy)-3-(4-methoxy-benzyloxy)-2,5-dimethyl-5-hexenal

Guidance literature:: Multi-step reaction with 4 steps

1.1: MgBr₂*Et₂O / CH₂Cl₂ / 0.5 h / -25 °C

1.2: 93 percent / CH₂Cl₂ / -25 - 23 °C

2.1: 79 percent / DDQ; 3 Angstroem molecular sieves / CH₂Cl₂ / 3.5 h

3.1: 77 percent / DIBAL / CH₂Cl₂ / 4 h / -78 - -20 °C

4.1: (COCl)2; DMSO / CH₂Cl₂ / 0.25 h / -78 °C

With oxalyl dichloride; 3 A molecular sieve; diisobutylaluminium hydride; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; magnesium bromide; In dichloromethane; 4.1: Swern oxidation;
DOI:10.1021/jo001236o