(2R,3R,3aS,7aR)-3-hydroxy-2-phenyl-1,2,3,3a-tetrahydropyrano-[3,2-b]pyrrol-5(7aH)-one

Base Information

Chemical Name:(2R,3R,3aS,7aR)-3-hydroxy-2-phenyl-1,2,3,3a-tetrahydropyrano-[3,2-b]pyrrol-5(7aH)-one
CAS No.:1356115-75-7
Molecular Formula:C₁₃H₁₃NO₃
Molecular Weight:231.251
Hs Code.:

Synonyms:

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Chemical Property of (2R,3R,3aS,7aR)-3-hydroxy-2-phenyl-1,2,3,3a-tetrahydropyrano-[3,2-b]pyrrol-5(7aH)-one

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Technology Process of (2R,3R,3aS,7aR)-3-hydroxy-2-phenyl-1,2,3,3a-tetrahydropyrano-[3,2-b]pyrrol-5(7aH)-one

There total 7 articles about (2R,3R,3aS,7aR)-3-hydroxy-2-phenyl-1,2,3,3a-tetrahydropyrano-[3,2-b]pyrrol-5(7aH)-one 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:

: C₁₈H₂₁NO₅

: 1356115-75-7
(2R,3R,3aS,7aR)-3-hydroxy-2-phenyl-1,2,3,3a-tetrahydropyrano-[3,2-b]pyrrol-5(7aH)-one

Guidance literature:: C₁₈H₂₁NO₅; With toluene-4-sulfonic acid; In acetonitrile; at 60 ℃; for 1h; Microwave irradiation;

With triethylamine; In acetonitrile;
DOI:10.1002/ejoc.201100886

Reference yield:

: 1356115-87-1
tert-butyl (3aS,4R,6R,6aR)-4-(hydroxymethyl)-2,2-dimethyl-6-phenyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-5(4H)-carboxylate

: 1356115-75-7
(2R,3R,3aS,7aR)-3-hydroxy-2-phenyl-1,2,3,3a-tetrahydropyrano-[3,2-b]pyrrol-5(7aH)-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 4-methylmorpholine N-oxide / dichloromethane / 0.17 h / Inert atmosphere; Molecular sieve

1.2: 0.33 h / 20 °C / Inert atmosphere; Molecular sieve

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 °C / Inert atmosphere

2.2: 1 h / Inert atmosphere

3.1: toluene-4-sulfonic acid / methanol / 0.5 h / 60 °C / Microwave irradiation

4.1: toluene-4-sulfonic acid / acetonitrile / 1 h / 60 °C / Microwave irradiation

With sodium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; mineral oil; 2.1: Horner-Wadsworth-Emmons olefination / 2.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1002/ejoc.201100886

Reference yield:

: 1356115-72-4
tert-butyl (2S,5S)-2-(hydroxymethyl)-5-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate

: 1356115-75-7
(2R,3R,3aS,7aR)-3-hydroxy-2-phenyl-1,2,3,3a-tetrahydropyrano-[3,2-b]pyrrol-5(7aH)-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: potassium osmate(VI) dihydrate; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 12 h / 20 °C

2.1: toluene-4-sulfonic acid / acetone / 1 h / Inert atmosphere

3.1: 4-methylmorpholine N-oxide / dichloromethane / 0.17 h / Inert atmosphere; Molecular sieve

3.2: 0.33 h / 20 °C / Inert atmosphere; Molecular sieve

4.1: sodium hydride / tetrahydrofuran; mineral oil / 0.25 h / 0 °C / Inert atmosphere

4.2: 1 h / Inert atmosphere

5.1: toluene-4-sulfonic acid / methanol / 0.5 h / 60 °C / Microwave irradiation

6.1: toluene-4-sulfonic acid / acetonitrile / 1 h / 60 °C / Microwave irradiation

With potassium osmate(VI) dihydrate; sodium hydride; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile; mineral oil; tert-butyl alcohol; 4.1: Horner-Wadsworth-Emmons olefination / 4.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1002/ejoc.201100886