(2R,4S,E)-methyl 2-hydroxy-7-(hydroxyimino)-4-phenyl-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-2-carboxylate

Base Information

Chemical Name:(2R,4S,E)-methyl 2-hydroxy-7-(hydroxyimino)-4-phenyl-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-2-carboxylate
CAS No.:1448818-72-1
Molecular Formula:C₁₆H₁₇NO₅
Molecular Weight:303.315
Hs Code.:

Synonyms:(2R,4S,E)-methyl 2-hydroxy-7-(hydroxyimino)-4-phenyl-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-2-carboxylate

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Chemical Property of (2R,4S,E)-methyl 2-hydroxy-7-(hydroxyimino)-4-phenyl-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-2-carboxylate

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Technology Process of (2R,4S,E)-methyl 2-hydroxy-7-(hydroxyimino)-4-phenyl-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-2-carboxylate

There total 4 articles about (2R,4S,E)-methyl 2-hydroxy-7-(hydroxyimino)-4-phenyl-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-2-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: 82.0%

: 80070-31-1
(E)-2-(hydroxyimino)cyclopentanone

: 107969-78-8
methyl benzylidenepyruvate

: 1448818-72-1
(2R,4S,E)-methyl 2-hydroxy-7-(hydroxyimino)-4-phenyl-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-2-carboxylate

Guidance literature:: With 1-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-3-((1R,2R)-2-(pyrrolidin-1-yl)cyclohexyl)thiourea; In toluene; at 20 ℃; for 24h; Reagent/catalyst; Solvent; stereoselective reaction;
DOI:10.1039/c3ob41001c

Reference yield:

: 80070-31-1
(E)-2-(hydroxyimino)cyclopentanone

: 107969-78-8
methyl benzylidenepyruvate

: 1448818-72-1
(2R,4S,E)-methyl 2-hydroxy-7-(hydroxyimino)-4-phenyl-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-2-carboxylate

: 1448818-89-0
(2S,4R,E)-methyl 2-hydroxy-7-(hydroxyimino)-4-phenyl-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-2-carboxylate

Guidance literature:: With 1-((1R,2R)-2-aminocyclohexyl)-3-(((1R,4aS,10ar)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)thiourea; In toluene; at 20 ℃; for 24h; Overall yield = 23 %; stereoselective reaction;
DOI:10.1039/c3ob41001c

Reference yield:

: 611-10-9
2-ethoxycarbonyl-1-cyclopentanone

: 1448818-72-1
(2R,4S,E)-methyl 2-hydroxy-7-(hydroxyimino)-4-phenyl-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydroxide; sodium nitrite / water / 48 h / 20 °C

1.2: 0 °C

2.1: 1-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-3-((1R,2R)-2-(pyrrolidin-1-yl)cyclohexyl)thiourea / toluene / 24 h / 20 °C

With 1-(((1R,4aS,10aR)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)-3-((1R,2R)-2-(pyrrolidin-1-yl)cyclohexyl)thiourea; sodium hydroxide; sodium nitrite; In water; toluene;
DOI:10.1039/c3ob41001c