(3S,5R,6R)-3-[2-(tert-butyldimethylsilanyloxy)-ethyl]-7-(4-methoxybenzyloxy)-6-methylheptane-1,5-diol

Base Information

Chemical Name:(3S,5R,6R)-3-[2-(tert-butyldimethylsilanyloxy)-ethyl]-7-(4-methoxybenzyloxy)-6-methylheptane-1,5-diol
CAS No.:423118-49-4
Molecular Formula:C₂₄H₄₄O₅Si
Molecular Weight:440.696
Hs Code.:

Synonyms:(3S,5R,6R)-3-[2-(tert-butyldimethylsilanyloxy)-ethyl]-7-(4-methoxybenzyloxy)-6-methylheptane-1,5-diol

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Chemical Property of (3S,5R,6R)-3-[2-(tert-butyldimethylsilanyloxy)-ethyl]-7-(4-methoxybenzyloxy)-6-methylheptane-1,5-diol

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Technology Process of (3S,5R,6R)-3-[2-(tert-butyldimethylsilanyloxy)-ethyl]-7-(4-methoxybenzyloxy)-6-methylheptane-1,5-diol

There total 11 articles about (3S,5R,6R)-3-[2-(tert-butyldimethylsilanyloxy)-ethyl]-7-(4-methoxybenzyloxy)-6-methylheptane-1,5-diol 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: 95.0%

: 423151-65-9
(2R,3R,5S)-5-[2-(tert-butyldimethylsilanyloxy)-ethyl]-1-(4-methoxybenzyloxy)-2-methylhept-6-en-3-ol

: 423118-49-4
(3S,5R,6R)-3-[2-(tert-butyldimethylsilanyloxy)-ethyl]-7-(4-methoxybenzyloxy)-6-methylheptane-1,5-diol

Guidance literature:: (2R,3R,5S)-5-[2-(tert-butyldimethylsilanyloxy)-ethyl]-1-(4-methoxybenzyloxy)-2-methylhept-6-en-3-ol; With 9-borabicyclo[3.3.1]nonane dimer; at 0 - 20 ℃; for 12h;

With sodium hydroxide; dihydrogen peroxide; at 0 ℃; for 4h;
DOI:10.1016/S0040-4039(01)02154-2

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 423118-49-4
(3S,5R,6R)-3-[2-(tert-butyldimethylsilanyloxy)-ethyl]-7-(4-methoxybenzyloxy)-6-methylheptane-1,5-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 62 percent / camphorsulfonic acid / CH₂Cl₂ / 72 h / 0 °C

2.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

3.1: 82 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

4.1: 9-BBN / tetrahydrofuran / 12.5 h / 0 - 20 °C

4.2: 95 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 4 h / 0 °C

With 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;
DOI:10.1039/b507570j

Reference yield:

: 423117-81-1
(α)-3-[2-(tert-butyldiphenylsilanyloxy)-ethyl]-pent-4-enal

: 423118-49-4
(3S,5R,6R)-3-[2-(tert-butyldimethylsilanyloxy)-ethyl]-7-(4-methoxybenzyloxy)-6-methylheptane-1,5-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: Bu₂BOTf; i-Pr₂NEt / CH₂Cl₂ / 0.5 h / -78 °C

1.2: 39 percent / CH₂Cl₂ / 2 h / -78 - 20 °C

2.1: 96 percent / LiBH₄ / methanol; diethyl ether / 2.5 h / 0 - 20 °C

3.1: 62 percent / camphorsulfonic acid / CH₂Cl₂ / 72 h / 0 °C

4.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

5.1: 82 percent / imidazole / CH₂Cl₂ / 2 h / 20 °C

6.1: 9-BBN / tetrahydrofuran / 12.5 h / 0 - 20 °C

6.2: 95 percent / aq. NaOH; H₂O₂ / tetrahydrofuran / 4 h / 0 °C

With 1H-imidazole; lithium borohydride; 9-borabicyclo[3.3.1]nonane dimer; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1.2: Evans aldol reaction;
DOI:10.1039/b507570j