6-{1-acetoxy-2-[2-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-5-oxo-cyclopentyl]-ethyl}-5a-formyl-8-hydroxy-2,2-dimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-9-carboxylic acid allyl ester

Base Information

Chemical Name:6-{1-acetoxy-2-[2-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-5-oxo-cyclopentyl]-ethyl}-5a-formyl-8-hydroxy-2,2-dimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-9-carboxylic acid allyl ester
CAS No.:872525-84-3
Molecular Formula:C₄₅H₅₆O₁₁Si
Molecular Weight:801.019
Hs Code.:

6-{1-acetoxy-2-[2-(<i>tert</i>-butyl-diphenyl-silanyloxymethyl)-1-methyl-5-oxo-cyclopentyl]-ethyl}-5a-formyl-8-hydroxy-2,2-dimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-<i>d</i>][1,3]dioxole-9-carboxylic acid allyl ester

Synonyms:6-{1-acetoxy-2-[2-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-5-oxo-cyclopentyl]-ethyl}-5a-formyl-8-hydroxy-2,2-dimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-9-carboxylic acid allyl ester

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Chemical Property of 6-{1-acetoxy-2-[2-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-5-oxo-cyclopentyl]-ethyl}-5a-formyl-8-hydroxy-2,2-dimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-9-carboxylic acid allyl ester

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Technology Process of 6-{1-acetoxy-2-[2-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-5-oxo-cyclopentyl]-ethyl}-5a-formyl-8-hydroxy-2,2-dimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-9-carboxylic acid allyl ester

There total 10 articles about 6-{1-acetoxy-2-[2-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-5-oxo-cyclopentyl]-ethyl}-5a-formyl-8-hydroxy-2,2-dimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-9-carboxylic acid allyl 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: 77.0%

: 872525-98-9
(3aR,7aS)-2,2-Dimethyl-6-oxo-3a,6,7,7a-tetrahydro-benzo[1,3]dioxole-5-carbaldehyde

: 493021-03-7
(E)-(R)-6-Acetoxy-7-[(1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-5-oxo-cyclopentyl]-3-oxo-hept-4-enoic acid allyl ester

: 872525-84-3
6-{1-acetoxy-2-[2-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-5-oxo-cyclopentyl]-ethyl}-5a-formyl-8-hydroxy-2,2-dimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-9-carboxylic acid allyl ester

Guidance literature:: With caesium carbonate; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1139/v05-042

Reference yield:

: 872525-77-4
2-(5-formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-N-methoxy-N-methyl-acetamide

: 872525-84-3
6-{1-acetoxy-2-[2-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-5-oxo-cyclopentyl]-ethyl}-5a-formyl-8-hydroxy-2,2-dimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-9-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 3.00 g / tetrahydrofuran; toluene / 1 h / 0 °C

2.1: 92 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 1 h / -78 °C

3.1: t-butyllithium / diethyl ether; pentane / 4 h / 0 °C

3.2: 98 percent / diethyl ether; pentane / 0.5 h / 0 °C

4.1: 73 percent / Grubb's second generation catalyst / CH₂Cl₂ / 40 °C

5.1: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

6.1: 77 percent / cesium carbonate / CH₂Cl₂ / 2 h / 20 °C

With tert.-butyl lithium; diisobutylaluminium hydride; caesium carbonate; Dess-Martin periodane; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; pentane; 1.1: Wittig reaction;
DOI:10.1139/v05-042

Reference yield:

: 872525-78-5
2-(2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-N-methoxy-N-methyl-acetamide

: 872525-84-3
6-{1-acetoxy-2-[2-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-5-oxo-cyclopentyl]-ethyl}-5a-formyl-8-hydroxy-2,2-dimethyl-5-oxo-3a,4,5,5a,6,7,9a,9b-octahydro-naphtho[1,2-d][1,3]dioxole-9-carboxylic acid allyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 92 percent / diisobutylaluminum hydride / tetrahydrofuran; toluene / 1 h / -78 °C

2.1: t-butyllithium / diethyl ether; pentane / 4 h / 0 °C

2.2: 98 percent / diethyl ether; pentane / 0.5 h / 0 °C

3.1: 73 percent / Grubb's second generation catalyst / CH₂Cl₂ / 40 °C

4.1: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

5.1: 77 percent / cesium carbonate / CH₂Cl₂ / 2 h / 20 °C

With tert.-butyl lithium; diisobutylaluminium hydride; caesium carbonate; Dess-Martin periodane; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; pentane;
DOI:10.1139/v05-042