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

Base Information

Chemical Name:(1S,5S,6R)-5,6-bis(benzyloxy)-3-((S)-(4-cyanophenyl)(hydroxy)methyl)-2-oxocyclohex-3-enyl acetate
CAS No.:1376712-09-2
Molecular Formula:C₃₀H₂₇NO₆
Molecular Weight:497.547
Hs Code.:

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

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Chemical Property of (1S,5S,6R)-5,6-bis(benzyloxy)-3-((S)-(4-cyanophenyl)(hydroxy)methyl)-2-oxocyclohex-3-enyl acetate

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Technology Process of (1S,5S,6R)-5,6-bis(benzyloxy)-3-((S)-(4-cyanophenyl)(hydroxy)methyl)-2-oxocyclohex-3-enyl acetate

There total 1 articles about (1S,5S,6R)-5,6-bis(benzyloxy)-3-((S)-(4-cyanophenyl)(hydroxy)methyl)-2-oxocyclohex-3-enyl 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: 71.0%

: 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

: 105-07-7
4-cyanobenzaldehyde

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

Guidance literature:: 2L-(2,4/3)-2-O-acetyl-3,4-di-O-benzyl-2,3,4-trihydroxy-5-cyclohexen-1-one; 4-cyanobenzaldehyde; With diethylaluminum iodide; In dichloromethane; toluene; at -78 - -50 ℃; for 8h; Inert atmosphere;

With water; sodium hydrogencarbonate; In dichloromethane; toluene; at -50 ℃; diastereoselective reaction; Inert atmosphere;
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

: C₃₀H₂₉NO₆

Guidance literature:: (1S,5S,6R)-5,6-bis(benzyloxy)-3-((S)-(4-cyanophenyl)(hydroxy)methyl)-2-oxocyclohex-3-enyl acetate; With cerium(III) chloride heptahydrate; In ethanol; at 0 ℃; for 0.5h;

With sodium tetrahydroborate; In ethanol; at 0 ℃; for 2h;
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