Heptanal, 7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-2, 6-dimethyl-, (2S,3S,6R)-

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Chemical Name:Heptanal, 7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-2, 6-dimethyl-, (2S,3S,6R)-
CAS No.:203387-44-4
Molecular Formula:C23H40O4Si
Molecular Weight:408.654
Hs Code.:

Synonyms:

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Chemical Property of Heptanal, 7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-2, 6-dimethyl-, (2S,3S,6R)-

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Technology Process of Heptanal, 7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-2, 6-dimethyl-, (2S,3S,6R)-

There total 15 articles about Heptanal, 7-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-[(4-methoxyphenyl)methoxy]-2, 6-dimethyl-, (2S,3S,6R)- 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: 97.0%

: 203387-53-5
(2R,3S,6R)-7-(tert-butyl(dimethyl)silyloxy)-3-(p-methoxybenzyloxy)-2,6-dimethylheptan-1-ol

: 203387-44-4
(2S,3S,6R)-7-(tert-butyl(dimethyl)silyloxy)-3-(p-methoxybenzyloxy)-2,6-dimethylheptan-1-al

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; cooling;
DOI:10.1021/jo035391p

Reference yield:

: 104701-87-3
(2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal

: 203387-44-4
(2S,3S,6R)-7-(tert-butyl(dimethyl)silyloxy)-3-(p-methoxybenzyloxy)-2,6-dimethylheptan-1-al

Guidance literature:: Multi-step reaction with 6 steps

1.1: aq. LiOH / tetrahydrofuran / 1 h / 22 °C

1.2: 90 percent / tetrahydrofuran / 16 h / 0 °C

2.1: 84 percent / BH₃*THF; (S)-CBS / tetrahydrofuran / 0.17 h / 0 °C

3.1: 95 percent / hydrazine hydrate; O₂; Cu(OAc)2

4.1: 76 percent / DDQ; 4 Angstroem molecular sieves / CH₂Cl₂

5.1: 91 percent / DIBALH / CH₂Cl₂ / -10 - 40 °C

6.1: 92 percent / oxalyl chloride; DMSO; N(i-Pr)Et₂ / CH₂Cl₂ / 0.33 h / -78 - 50 °C

With lithium hydroxide; copper diacetate; borane-THF; oxalyl dichloride; (S)-diphenylprolinol; N,N-diethyl-N-isopropylamine; 4 A molecular sieve; oxygen; diisobutylaluminium hydride; hydrazine hydrate; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; 1.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1055/s-2005-863705

Reference yield:

: 203387-42-2
(2R,3S,6R)-7-(tert-butyl(dimethyl)silyloxy)-1-(p-methoxybenzyloxy)-2,6-dimethyl-hept-4-en-3-ol

: 203387-44-4
(2S,3S,6R)-7-(tert-butyl(dimethyl)silyloxy)-3-(p-methoxybenzyloxy)-2,6-dimethylheptan-1-al

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / hydrazine hydrate; O₂; Cu(OAc)2

2: 76 percent / DDQ; 4 Angstroem molecular sieves / CH₂Cl₂

3: 91 percent / DIBALH / CH₂Cl₂ / -10 - 40 °C

4: 92 percent / oxalyl chloride; DMSO; N(i-Pr)Et₂ / CH₂Cl₂ / 0.33 h / -78 - 50 °C

With copper diacetate; oxalyl dichloride; N,N-diethyl-N-isopropylamine; 4 A molecular sieve; oxygen; diisobutylaluminium hydride; hydrazine hydrate; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;
DOI:10.1055/s-2005-863705