(E,8S,9S)-1-(benzyloxy)-8-(methoxymethoxy)-9-(tert-butyldimethylsilyloxy)trideca-6,12-dien-5-one

Base Information

Chemical Name:(E,8S,9S)-1-(benzyloxy)-8-(methoxymethoxy)-9-(tert-butyldimethylsilyloxy)trideca-6,12-dien-5-one
CAS No.:1322008-03-6
Molecular Formula:C₂₈H₄₆O₅Si
Molecular Weight:490.756
Hs Code.:

Synonyms:(E,8S,9S)-1-(benzyloxy)-8-(methoxymethoxy)-9-(tert-butyldimethylsilyloxy)trideca-6,12-dien-5-one

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (E,8S,9S)-1-(benzyloxy)-8-(methoxymethoxy)-9-(tert-butyldimethylsilyloxy)trideca-6,12-dien-5-one

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Pictogram(s):
Hazard Codes:

MSDS Files:

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Technology Process of (E,8S,9S)-1-(benzyloxy)-8-(methoxymethoxy)-9-(tert-butyldimethylsilyloxy)trideca-6,12-dien-5-one

There total 9 articles about (E,8S,9S)-1-(benzyloxy)-8-(methoxymethoxy)-9-(tert-butyldimethylsilyloxy)trideca-6,12-dien-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:

: 1322008-01-4
(S,E)-5-(tert-butyldimethylsilyloxy)-4-oxonona-2,8-dienal

: 1322008-03-6
(E,8S,9S)-1-(benzyloxy)-8-(methoxymethoxy)-9-(tert-butyldimethylsilyloxy)trideca-6,12-dien-5-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 3 h / 20 °C / pH 3.6 / Inert atmosphere; aq. phosphate buffer

1.2: pH 4 / Inert atmosphere

2.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

3.1: triethylamine / dichloromethane / 1 h / Inert atmosphere

4.1: cerium(III) chloride heptahydrate / methanol / 1 h / 20 °C / Inert atmosphere

4.2: 2 h / -78 °C / Inert atmosphere

5.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 6.25 h / 0 °C / Inert atmosphere; Reflux

6.1: tetrahydrofuran / -10 - 0 °C / Inert atmosphere

6.2: Inert atmosphere

With dmap; sodium chlorite; 2-methyl-but-2-ene; cerium(III) chloride heptahydrate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol;
DOI:10.1021/ol201604c

Reference yield:

: 98-01-1
furfural

: 1322008-03-6
(E,8S,9S)-1-(benzyloxy)-8-(methoxymethoxy)-9-(tert-butyldimethylsilyloxy)trideca-6,12-dien-5-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: titanium(IV) isopropylate; D-(-)-diisopropyl tartrate / dichloromethane / -30 °C / Inert atmosphere

2.2: 24 h / -20 °C / Inert atmosphere

3.1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 6 h / 20 °C / Inert atmosphere

4.1: N-Bromosuccinimide; water; sodium hydrogencarbonate / acetone / 2 h / -15 °C / Inert atmosphere

4.2: 1 h / Inert atmosphere

4.3: -15 - 20 °C / Inert atmosphere

5.1: sodium chlorite; 2-methyl-but-2-ene / water; tert-butyl alcohol / 3 h / 20 °C / pH 3.6 / Inert atmosphere; aq. phosphate buffer

5.2: pH 4 / Inert atmosphere

6.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

7.1: triethylamine / dichloromethane / 1 h / Inert atmosphere

8.1: cerium(III) chloride heptahydrate / methanol / 1 h / 20 °C / Inert atmosphere

8.2: 2 h / -78 °C / Inert atmosphere

9.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 6.25 h / 0 °C / Inert atmosphere; Reflux

10.1: tetrahydrofuran / -10 - 0 °C / Inert atmosphere

10.2: Inert atmosphere

With 1H-imidazole; titanium(IV) isopropylate; dmap; sodium chlorite; N-Bromosuccinimide; 2-methyl-but-2-ene; cerium(III) chloride heptahydrate; D-(-)-diisopropyl tartrate; water; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
DOI:10.1021/ol201604c

Reference yield:

: 1322007-92-0
(S,E)-5-(tert-butyldimethylsilyloxy)-4-oxonona-2,8-dienoic acid

: 1322008-03-6
(E,8S,9S)-1-(benzyloxy)-8-(methoxymethoxy)-9-(tert-butyldimethylsilyloxy)trideca-6,12-dien-5-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 1 h / Inert atmosphere

3.1: cerium(III) chloride heptahydrate / methanol / 1 h / 20 °C / Inert atmosphere

3.2: 2 h / -78 °C / Inert atmosphere

4.1: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 6.25 h / 0 °C / Inert atmosphere; Reflux

5.1: tetrahydrofuran / -10 - 0 °C / Inert atmosphere

5.2: Inert atmosphere

With dmap; cerium(III) chloride heptahydrate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ol201604c