(S)-2-((3aS,4R,6aR)-4-Benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-yl)-2-phenyl-ethanol

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Chemical Name:(S)-2-((3aS,4R,6aR)-4-Benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-yl)-2-phenyl-ethanol
CAS No.:239136-90-4
Molecular Formula:C₂₃H₂₉NO₄
Molecular Weight:383.488
Hs Code.:

Synonyms:(S)-2-((3aS,4R,6aR)-4-Benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-yl)-2-phenyl-ethanol

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Chemical Property of (S)-2-((3aS,4R,6aR)-4-Benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-yl)-2-phenyl-ethanol

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Technology Process of (S)-2-((3aS,4R,6aR)-4-Benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-yl)-2-phenyl-ethanol

There total 10 articles about (S)-2-((3aS,4R,6aR)-4-Benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-yl)-2-phenyl-ethanol 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: 81.0%

: 176095-95-7
(3aR,3bR,6S,7aS)-3b-Benzyloxymethyl-2,2-dimethyl-6-phenyl-tetrahydro-1,3,4-trioxa-6a-aza-cyclopenta[a]pentalen-7-one

: 239136-90-4
(S)-2-((3aS,4R,6aR)-4-Benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-yl)-2-phenyl-ethanol

Guidance literature:: With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; Heating;
DOI:10.1021/jo960129k

Reference yield:

: 167645-47-8
5-(benzyloxy)-4-oxopentanoic acid

: 239136-90-4
(S)-2-((3aS,4R,6aR)-4-Benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-yl)-2-phenyl-ethanol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 7.4 g / benzene / 6 h / Heating

2.1: LiHMDS; PhSO₂Me / tetrahydrofuran

2.2: 85 percent / Na₂CO₃ / toluene / 6 h / Heating

3.1: 64 percent / OsO₄; NMO / acetone; H₂O / 48 h / 20 °C

4.1: 98 percent / p-TsOH / CH₂Cl₂ / 0.5 h / 20 °C

5.1: 81 percent / 9-BBN / tetrahydrofuran / 24 h / Heating

With osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; N-methyl-2-indolinone; methylphenylsulfonate; toluene-4-sulfonic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; acetone; benzene; 1.1: Acylation / 2.1: Oxidation / 2.2: Elimination / 3.1: Oxidation / 4.1: Etherification / 5.1: Reduction;
DOI:10.1016/S0040-4020(99)00454-8

Reference yield:

: 176298-36-5
(3S,7aS)-7a-Benzyloxymethyl-3-phenyl-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

: 239136-90-4
(S)-2-((3aS,4R,6aR)-4-Benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-yl)-2-phenyl-ethanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: LiHMDS; PhSO₂Me / tetrahydrofuran

1.2: 85 percent / Na₂CO₃ / toluene / 6 h / Heating

2.1: 64 percent / OsO₄; NMO / acetone; H₂O / 48 h / 20 °C

3.1: 98 percent / p-TsOH / CH₂Cl₂ / 0.5 h / 20 °C

4.1: 81 percent / 9-BBN / tetrahydrofuran / 24 h / Heating

With osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; N-methyl-2-indolinone; methylphenylsulfonate; toluene-4-sulfonic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; acetone; 1.1: Oxidation / 1.2: Elimination / 2.1: Oxidation / 3.1: Etherification / 4.1: Reduction;
DOI:10.1016/S0040-4020(99)00454-8