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

Base Information

Chemical Name:(E,5R,8S,9S)-1-(benzyloxy)-8-(methoxymethoxy)-9-(tert-butyldimethylsilyloxy)trideca-6,12-dien-5-ol
CAS No.:1322008-05-8
Molecular Formula:C₂₈H₄₈O₅Si
Molecular Weight:492.772
Hs Code.:

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

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

Chemical Property:

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

There total 11 articles about (E,5R,8S,9S)-1-(benzyloxy)-8-(methoxymethoxy)-9-(tert-butyldimethylsilyloxy)trideca-6,12-dien-5-ol 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:

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

: 1322008-05-8
(E,5R,8S,9S)-1-(benzyloxy)-8-(methoxymethoxy)-9-(tert-butyldimethylsilyloxy)trideca-6,12-dien-5-ol

: 1322008-04-7
(E,5S,8S,9S)-1-(benzyloxy)-8-(methoxymethoxy)-9-(tert-butyldimethylsilyloxy)trideca-6,12-dien-5-ol

Guidance literature:: (E,8S,9S)-1-(benzyloxy)-8-(methoxymethoxy)-9-(tert-butyldimethylsilyloxy)trideca-6,12-dien-5-one; With (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at -40 ℃; for 0.5h; Inert atmosphere;

With dimethylsulfide borane complex; In tetrahydrofuran; toluene; at -40 ℃; for 1h; Inert atmosphere;

With water; sodium hydrogencarbonate; In tetrahydrofuran; methanol; toluene; optical yield given as %de; Inert atmosphere;
DOI:10.1021/ol201604c

Reference yield:

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

: 1322008-05-8
(E,5R,8S,9S)-1-(benzyloxy)-8-(methoxymethoxy)-9-(tert-butyldimethylsilyloxy)trideca-6,12-dien-5-ol

Guidance literature:: Multi-step reaction with 7 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

7.1: cerium(III) chloride heptahydrate / methanol / 0.25 h / 20 °C / Inert atmosphere

7.2: 0 °C / 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

: 1322008-05-8
(E,5R,8S,9S)-1-(benzyloxy)-8-(methoxymethoxy)-9-(tert-butyldimethylsilyloxy)trideca-6,12-dien-5-ol

Guidance literature:: Multi-step reaction with 11 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

11.1: cerium(III) chloride heptahydrate / methanol / 0.25 h / 20 °C / Inert atmosphere

11.2: 0 °C / 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