10-{6-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propenyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-3-hydroxy-deca-4,6,8-trienoic acid tert-butyl ester

Base Information

Chemical Name:10-{6-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propenyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-3-hydroxy-deca-4,6,8-trienoic acid tert-butyl ester
CAS No.:933466-24-1
Molecular Formula:C₄₁H₅₈O₆Si
Molecular Weight:674.993
Hs Code.:

10-{6-[3-(<i>tert</i>-butyl-diphenyl-silanyloxy)-1-methyl-propenyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-3-hydroxy-deca-4,6,8-trienoic acid <i>tert</i>-butyl ester

Synonyms:10-{6-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propenyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-3-hydroxy-deca-4,6,8-trienoic acid tert-butyl ester

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Chemical Property of 10-{6-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propenyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-3-hydroxy-deca-4,6,8-trienoic acid tert-butyl ester

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Technology Process of 10-{6-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propenyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-3-hydroxy-deca-4,6,8-trienoic acid tert-butyl ester

There total 5 articles about 10-{6-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propenyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-3-hydroxy-deca-4,6,8-trienoic acid tert-butyl ester 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:

: (2E,4E)-8-{(4S,5S,6R)-6-[(Z)-3-(tert-butyldiphenylsiloxy)-1-methylprop-1-enyl]-2,2,5-trimethyl-1,3-dioxan-4-yl}octa-2,4,6-trienal

: 540-88-5
acetic acid tert-butyl ester

: 10-{6-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propenyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-3-hydroxy-deca-4,6,8-trienoic acid tert-butyl ester

: 933466-24-1
10-{6-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propenyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-3-hydroxy-deca-4,6,8-trienoic acid tert-butyl ester

Guidance literature:: With 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose; triethylamine; lithium diisopropyl amide; cyclopentadienyl titanium(IV) trichloride; In diethyl ether; at -78 - -65 ℃; for 12h;
DOI:10.1055/s-2006-958967

Reference yield:

: 933466-20-7
2-{(4S,5S,6R)-6-[(Z)-3-(tert-butyldiphenylsiloxy)-1-methylprop-1-enyl]-2,2,5-trimethyl-1,3-dioxan-4-yl}ethanal

: 933466-24-1
10-{6-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propenyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-3-hydroxy-deca-4,6,8-trienoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

1.2: 96 percent / tetrahydrofuran / 12 h / -78 - -10 °C

2.1: 96 percent / DIBAL-H / tetrahydrofuran; toluene / 2 h / -78 °C

3.1: 72 percent / NMO; tetrapropylammonium perruthenate / CH₂Cl₂ / 2 h / 20 °C

4.1: diacetone-D-glucose; LDA; Et₃N / CpTiCl₃ / diethyl ether / 12 h / -78 - -65 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose; diisobutylaluminium hydride; triethylamine; lithium hexamethyldisilazane; lithium diisopropyl amide; cyclopentadienyl titanium(IV) trichloride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 1.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1055/s-2006-958967

Reference yield:

: ethyl {(4S,5S,6R)-6-[(Z)-3-(tert-butyldiphenylsiloxy)-1-methylprop-1-enyl]-2,2,5-trimethyl-1,3-dioxan-4-yl}acetate

: 933466-24-1
10-{6-[3-(tert-butyl-diphenyl-silanyloxy)-1-methyl-propenyl]-2,2,5-trimethyl-[1,3]dioxan-4-yl}-3-hydroxy-deca-4,6,8-trienoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 99 percent / DIBAL-H / CH₂Cl₂; toluene / 2 h / -78 °C

2.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: 96 percent / tetrahydrofuran / 12 h / -78 - -10 °C

3.1: 96 percent / DIBAL-H / tetrahydrofuran; toluene / 2 h / -78 °C

4.1: 72 percent / NMO; tetrapropylammonium perruthenate / CH₂Cl₂ / 2 h / 20 °C

5.1: diacetone-D-glucose; LDA; Et₃N / CpTiCl₃ / diethyl ether / 12 h / -78 - -65 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose; diisobutylaluminium hydride; triethylamine; lithium hexamethyldisilazane; lithium diisopropyl amide; cyclopentadienyl titanium(IV) trichloride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 2.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1055/s-2006-958967