(4S,6S,7R,8R,8aS)-6,7-bis(benzyloxy)-4-(4-cyanophenyl)-2,2-dimethyl-6,7,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-yl acetate

Base Information

Chemical Name:(4S,6S,7R,8R,8aS)-6,7-bis(benzyloxy)-4-(4-cyanophenyl)-2,2-dimethyl-6,7,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-yl acetate
CAS No.:1376712-18-3
Molecular Formula:C₃₃H₃₃NO₆
Molecular Weight:539.628
Hs Code.:

Synonyms:(4S,6S,7R,8R,8aS)-6,7-bis(benzyloxy)-4-(4-cyanophenyl)-2,2-dimethyl-6,7,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-yl acetate

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Chemical Property of (4S,6S,7R,8R,8aS)-6,7-bis(benzyloxy)-4-(4-cyanophenyl)-2,2-dimethyl-6,7,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-yl acetate

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Technology Process of (4S,6S,7R,8R,8aS)-6,7-bis(benzyloxy)-4-(4-cyanophenyl)-2,2-dimethyl-6,7,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-yl acetate

There total 3 articles about (4S,6S,7R,8R,8aS)-6,7-bis(benzyloxy)-4-(4-cyanophenyl)-2,2-dimethyl-6,7,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-yl acetate 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:

: C₃₀H₂₉NO₆

: 77-76-9
2,2-dimethoxy-propane

: 1376712-18-3
(4S,6S,7R,8R,8aS)-6,7-bis(benzyloxy)-4-(4-cyanophenyl)-2,2-dimethyl-6,7,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-yl acetate

Guidance literature:: With camphor-10-sulfonic acid; In acetone; for 12h;
DOI:10.1016/j.tetasy.2012.03.009

Reference yield:

: 1376712-09-2
(1S,5S,6R)-5,6-bis(benzyloxy)-3-((S)-(4-cyanophenyl)(hydroxy)methyl)-2-oxocyclohex-3-enyl acetate

: 1376712-18-3
(4S,6S,7R,8R,8aS)-6,7-bis(benzyloxy)-4-(4-cyanophenyl)-2,2-dimethyl-6,7,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-yl acetate

Guidance literature:: Multi-step reaction with 2 steps

1.1: cerium(III) chloride heptahydrate / ethanol / 0.5 h / 0 °C

1.2: 2 h / 0 °C

2.1: camphor-10-sulfonic acid / acetone / 12 h

With cerium(III) chloride heptahydrate; camphor-10-sulfonic acid; In ethanol; acetone; 1.1: Luche reduction / 1.2: Luche reduction;
DOI:10.1016/j.tetasy.2012.03.009

Reference yield:

: 136458-74-7,136458-76-9,122777-36-0
2L-(2,4/3)-2-O-acetyl-3,4-di-O-benzyl-2,3,4-trihydroxy-5-cyclohexen-1-one

: 1376712-18-3
(4S,6S,7R,8R,8aS)-6,7-bis(benzyloxy)-4-(4-cyanophenyl)-2,2-dimethyl-6,7,8,8a-tetrahydro-4H-benzo[d][1,3]dioxin-8-yl acetate

Guidance literature:: Multi-step reaction with 3 steps

1.1: diethylaluminum iodide / dichloromethane; toluene / 8 h / -78 - -50 °C / Inert atmosphere

1.2: -50 °C / Inert atmosphere

2.1: cerium(III) chloride heptahydrate / ethanol / 0.5 h / 0 °C

2.2: 2 h / 0 °C

3.1: camphor-10-sulfonic acid / acetone / 12 h

With cerium(III) chloride heptahydrate; camphor-10-sulfonic acid; diethylaluminum iodide; In ethanol; dichloromethane; acetone; toluene; 1.1: Morita-Baylis-Hillman reaction / 2.1: Luche reduction / 2.2: Luche reduction;
DOI:10.1016/j.tetasy.2012.03.009