(3E,9E,11E)-(S)-1-[(4R,6S)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-8-(tert-butyl-dimethyl-silanyloxy)-trideca-3,9,11-trien-5-one

Base Information

Chemical Name:(3E,9E,11E)-(S)-1-[(4R,6S)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-8-(tert-butyl-dimethyl-silanyloxy)-trideca-3,9,11-trien-5-one
CAS No.:82080-54-4
Molecular Formula:C₃₄H₅₄O₅Si
Molecular Weight:570.885
Hs Code.:

Synonyms:(3E,9E,11E)-(S)-1-[(4R,6S)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-8-(tert-butyl-dimethyl-silanyloxy)-trideca-3,9,11-trien-5-one

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Chemical Property of (3E,9E,11E)-(S)-1-[(4R,6S)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-8-(tert-butyl-dimethyl-silanyloxy)-trideca-3,9,11-trien-5-one

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Technology Process of (3E,9E,11E)-(S)-1-[(4R,6S)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-8-(tert-butyl-dimethyl-silanyloxy)-trideca-3,9,11-trien-5-one

There total 9 articles about (3E,9E,11E)-(S)-1-[(4R,6S)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-8-(tert-butyl-dimethyl-silanyloxy)-trideca-3,9,11-trien-5-one 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: 86.0%

: 82065-58-5
3-[(4R,6S)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-propionaldehyde

: 82065-57-4
[(6E,8E)-(S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-oxo-deca-6,8-dienyl]-phosphonic acid dimethyl ester

: 82080-54-4
(3E,9E,11E)-(S)-1-[(4R,6S)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-8-(tert-butyl-dimethyl-silanyloxy)-trideca-3,9,11-trien-5-one

Guidance literature:: With sodium hydride; In tetrahydrofuran; 1.) 0 deg C, 5 min, 2.) 25 deg C, 10 min;
DOI:10.1021/ja00379a037

Reference yield:

: 100-39-0
benzyl bromide

: 82080-54-4
(3E,9E,11E)-(S)-1-[(4R,6S)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-8-(tert-butyl-dimethyl-silanyloxy)-trideca-3,9,11-trien-5-one

Guidance literature:: Multi-step reaction with 3 steps

1: NaH / dimethylformamide

2: 88 percent / O₃ / methanol / -78 °C

3: 86 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 5 min, 2.) 25 deg C, 10 min

With sodium hydride; ozone; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/ja00379a037

Reference yield:

: 82065-65-4
(R)-3-[(tetrahydro-2H-pyran-2-yl)oxy]-6-heptenal

: 82080-54-4
(3E,9E,11E)-(S)-1-[(4R,6S)-6-(2-Benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-8-(tert-butyl-dimethyl-silanyloxy)-trideca-3,9,11-trien-5-one

Guidance literature:: Multi-step reaction with 7 steps

1: LDA / -78 °C

2: PPTS / ethanol

3: p-TsOH

4: LiAlH₄

5: NaH / dimethylformamide

6: 88 percent / O₃ / methanol / -78 °C

7: 86 percent / NaH / tetrahydrofuran / 1.) 0 deg C, 5 min, 2.) 25 deg C, 10 min

With lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; ozone; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide;
DOI:10.1021/ja00379a037