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

Base Information

Chemical Name:(1S,5S,6R)-5,6-bis(benzyloxy)-3-((R)-(2,3-dichlorophenyl)-(hydroxy)methyl)-2-oxocyclohex-3-enyl 4-nitrobenzoate
CAS No.:1376712-17-2
Molecular Formula:C₃₄H₂₇Cl₂NO₈
Molecular Weight:648.496
Hs Code.:

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

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

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

There total 4 articles about (1S,5S,6R)-5,6-bis(benzyloxy)-3-((R)-(2,3-dichlorophenyl)-(hydroxy)methyl)-2-oxocyclohex-3-enyl 4-nitrobenzoate 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: 49.0%

: 1376712-06-9
C₂₇H₂₃NO₇

: 6334-18-5
2,3-dichlorobenzylaldehyde

: 1376712-17-2
(1S,5S,6R)-5,6-bis(benzyloxy)-3-((R)-(2,3-dichlorophenyl)-(hydroxy)methyl)-2-oxocyclohex-3-enyl 4-nitrobenzoate

Guidance literature:: C₂₇H₂₃NO₇; 2,3-dichlorobenzylaldehyde; 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:

: 1376712-07-0
(3S,4S,5R,6S)-4,5-bis(benzyloxy)-6-methoxy-2-methylenetetrahydro-2H-pyran-3-yl 4-nitrobenzoate

: 1376712-17-2
(1S,5S,6R)-5,6-bis(benzyloxy)-3-((R)-(2,3-dichlorophenyl)-(hydroxy)methyl)-2-oxocyclohex-3-enyl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: water; mercury(II) trifluoroacetate / acetone / 12 h

2.1: methanesulfonyl chloride; triethylamine / dichloromethane / 2 h / 0 - 20 °C

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

3.2: -50 °C / Inert atmosphere

With water; mercury(II) trifluoroacetate; diethylaluminum iodide; methanesulfonyl chloride; triethylamine; In dichloromethane; acetone; toluene; 3.1: Morita-Baylis-Hillman reaction;
DOI:10.1016/j.tetasy.2012.03.009

Reference yield:

: C₂₇H₂₅NO₈

: 1376712-17-2
(1S,5S,6R)-5,6-bis(benzyloxy)-3-((R)-(2,3-dichlorophenyl)-(hydroxy)methyl)-2-oxocyclohex-3-enyl 4-nitrobenzoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: methanesulfonyl chloride; triethylamine / dichloromethane / 2 h / 0 - 20 °C

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

2.2: -50 °C / Inert atmosphere

With diethylaluminum iodide; methanesulfonyl chloride; triethylamine; In dichloromethane; toluene; 2.1: Morita-Baylis-Hillman reaction;
DOI:10.1016/j.tetasy.2012.03.009