(1R,3S,4R,5R)-ethyl 3-(1,3-dioxoisoindolin-2-yl)-5-hydroxy-4-(4-methylphenylsulfonamido)cyclohexanecarboxylate

Base Information

Chemical Name:(1R,3S,4R,5R)-ethyl 3-(1,3-dioxoisoindolin-2-yl)-5-hydroxy-4-(4-methylphenylsulfonamido)cyclohexanecarboxylate
CAS No.:1291089-93-4
Molecular Formula:C₂₄H₂₆N₂O₇S
Molecular Weight:486.546
Hs Code.:

Synonyms:(1R,3S,4R,5R)-ethyl 3-(1,3-dioxoisoindolin-2-yl)-5-hydroxy-4-(4-methylphenylsulfonamido)cyclohexanecarboxylate

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Chemical Property of (1R,3S,4R,5R)-ethyl 3-(1,3-dioxoisoindolin-2-yl)-5-hydroxy-4-(4-methylphenylsulfonamido)cyclohexanecarboxylate

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Technology Process of (1R,3S,4R,5R)-ethyl 3-(1,3-dioxoisoindolin-2-yl)-5-hydroxy-4-(4-methylphenylsulfonamido)cyclohexanecarboxylate

There total 9 articles about (1R,3S,4R,5R)-ethyl 3-(1,3-dioxoisoindolin-2-yl)-5-hydroxy-4-(4-methylphenylsulfonamido)cyclohexanecarboxylate 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: 100.0%

: 1291089-91-2
(1S,3R,5S,6R)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-7-tosyl-7-aza-bicyclo[4.1.0]heptane-3-carboxylate

: 1291089-93-4
(1R,3S,4R,5R)-ethyl 3-(1,3-dioxoisoindolin-2-yl)-5-hydroxy-4-(4-methylphenylsulfonamido)cyclohexanecarboxylate

Guidance literature:: With aluminium(III) triflate; 2,6-di-tert-butyl-pyridine; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1002/chem.201003454

Reference yield: 50.0%

: 1291089-91-2
(1S,3R,5S,6R)-ethyl 5-(1,3-dioxoisoindolin-2-yl)-7-tosyl-7-aza-bicyclo[4.1.0]heptane-3-carboxylate

: 1291089-95-6
(1R,3S,4R)-ethyl 3-(1,3-dioxoisoindolin-2-yl)-4-(4-methylphenylsulfonamido)-5-oxocyclohexanecarboxylate

: 1291089-93-4
(1R,3S,4R,5R)-ethyl 3-(1,3-dioxoisoindolin-2-yl)-5-hydroxy-4-(4-methylphenylsulfonamido)cyclohexanecarboxylate

Guidance literature:: With indium(III) triflate; dimethyl sulfoxide; at 120 ℃; Inert atmosphere;
DOI:10.1002/chem.201003454

Reference yield:

: 4720-83-6
6-oxabicyclo<3.2.1>-oct-3-en-7-one

: 1291089-93-4
(1R,3S,4R,5R)-ethyl 3-(1,3-dioxoisoindolin-2-yl)-5-hydroxy-4-(4-methylphenylsulfonamido)cyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: bis(η3-allyl-μ-chloropalladium(II)); (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane / tetrahydrofuran / 0.33 h / 40 °C / Inert atmosphere

1.2: 8 h / 40 °C / Inert atmosphere

1.3: 10 h / Inert atmosphere; Reflux

2.1: Cu(MeCN)4*PF₆ / acetonitrile / Inert atmosphere; Molecular sieve

3.1: indium(III) triflate; 2,6-di-tert-butyl-pyridine / chlorobenzene / 100 °C / Inert atmosphere

With indium(III) triflate; 2,6-di-tert-butyl-pyridine; bis(η3-allyl-μ-chloropalladium(II)); Cu(MeCN)4*PF₆; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; In tetrahydrofuran; chlorobenzene; acetonitrile;
DOI:10.1002/chem.201003454