(2S,3R,4R)-2-(cyclohexanecarbonyloxy)-4-hydroxypentan-3-yl 2,5-dihydro-1H-pyrrole-1-carboxylate

Base Information

Chemical Name:(2S,3R,4R)-2-(cyclohexanecarbonyloxy)-4-hydroxypentan-3-yl 2,5-dihydro-1H-pyrrole-1-carboxylate
CAS No.:1332880-39-3
Molecular Formula:C₁₇H₂₇NO₅
Molecular Weight:325.405
Hs Code.:

Synonyms:(2S,3R,4R)-2-(cyclohexanecarbonyloxy)-4-hydroxypentan-3-yl 2,5-dihydro-1H-pyrrole-1-carboxylate

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Chemical Property of (2S,3R,4R)-2-(cyclohexanecarbonyloxy)-4-hydroxypentan-3-yl 2,5-dihydro-1H-pyrrole-1-carboxylate

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Technology Process of (2S,3R,4R)-2-(cyclohexanecarbonyloxy)-4-hydroxypentan-3-yl 2,5-dihydro-1H-pyrrole-1-carboxylate

There total 6 articles about (2S,3R,4R)-2-(cyclohexanecarbonyloxy)-4-hydroxypentan-3-yl 2,5-dihydro-1H-pyrrole-1-carboxylate 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%

: (2R,3s,4S)-2,4-dihydroxypentan-3-yl 2,5-dihydro-1H-pyrrole-1-carboxylate

: 22651-87-2
cyclohexanecarboxylic acid anhydride

: 1332880-39-3
(2S,3R,4R)-2-(cyclohexanecarbonyloxy)-4-hydroxypentan-3-yl 2,5-dihydro-1H-pyrrole-1-carboxylate

: (2R,3s,4S)-3-(2,5-dihydro-1H-pyrrole-1-carbonyloxy)pentane-2,4-diyl dicyclohexanecarboxylate

Guidance literature:: With (S)-(-)-1-tris(trimethylsilyl)silyloxy-3-(3'-methyl-3'H-imidazol-4'-yl)-2-(2'',4'',6''-triisopropylbenzenesulfonylamino)propane; N-ethyl-N,N-diisopropylamine; In tetrachloromethane; chloroform; at 20 ℃; for 4h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
DOI:10.1002/adsc.201100252

Reference yield:

: (2R,3s,4S)-2,4-dihydroxypentan-3-yl 2,5-dihydro-1H-pyrrole-1-carboxylate

: 22651-87-2
cyclohexanecarboxylic acid anhydride

: (2R,3S,4S)-2-(cyclohexanecarbonyloxy)-4-hydroxypentan-3-yl 2,5-dihydro-1H-pyrrole-1-carboxylate

: 1332880-39-3
(2S,3R,4R)-2-(cyclohexanecarbonyloxy)-4-hydroxypentan-3-yl 2,5-dihydro-1H-pyrrole-1-carboxylate

: (2R,3s,4S)-3-(2,5-dihydro-1H-pyrrole-1-carbonyloxy)pentane-2,4-diyl dicyclohexanecarboxylate

Guidance literature:: With (S)-(-)-1-tris(trimethylsilyl)silyloxy-3-(3'-methyl-3'H-imidazol-4'-yl)-2-(2'',4'',6''-triisopropylbenzenesulfonylamino)propane; N-ethyl-N,N-diisopropylamine; In tetrachloromethane; chloroform; at 20 ℃; for 24h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
DOI:10.1002/adsc.201100252

Reference yield:

: 1332880-57-5
(4S,5s,6R)-5-(benzyloxy)-2,2,4,6-tetramethyl-1,3-dioxane

: 1332880-39-3
(2S,3R,4R)-2-(cyclohexanecarbonyloxy)-4-hydroxypentan-3-yl 2,5-dihydro-1H-pyrrole-1-carboxylate

: (2R,3s,4S)-3-(2,5-dihydro-1H-pyrrole-1-carbonyloxy)pentane-2,4-diyl dicyclohexanecarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: ammonia; sodium / tetrahydrofuran; ethanol; isopropyl alcohol / 2 h / -78 °C / Inert atmosphere

2: dmap; sodium hydride / N,N-dimethyl-formamide; mineral oil / 5 h / 0 - 50 °C / Inert atmosphere

3: water; acetic acid / 3 h / 50 °C / Inert atmosphere

4: (S)-(-)-1-tris(trimethylsilyl)silyloxy-3-(3'-methyl-3'H-imidazol-4'-yl)-2-(2'',4'',6''-triisopropylbenzenesulfonylamino)propane; N-ethyl-N,N-diisopropylamine / tetrachloromethane; chloroform / 4 h / 20 °C / Inert atmosphere

With dmap; (S)-(-)-1-tris(trimethylsilyl)silyloxy-3-(3'-methyl-3'H-imidazol-4'-yl)-2-(2'',4'',6''-triisopropylbenzenesulfonylamino)propane; ammonia; water; sodium; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; tetrachloromethane; ethanol; chloroform; N,N-dimethyl-formamide; isopropyl alcohol; mineral oil;
DOI:10.1002/adsc.201100252