((3R,3aS,4S,6aS)-4-((2R,3R)-4-(benzyloxy)-3-(ethanoyloxy)-2-methylbutyl)-3a-hydroxy-1,3-dimethyl-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrol-6a-yl)methyl ethanoate

Base Information

Chemical Name:((3R,3aS,4S,6aS)-4-((2R,3R)-4-(benzyloxy)-3-(ethanoyloxy)-2-methylbutyl)-3a-hydroxy-1,3-dimethyl-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrol-6a-yl)methyl ethanoate
CAS No.:1352406-02-0
Molecular Formula:C₂₅H₃₃NO₉
Molecular Weight:491.538
Hs Code.:

((3R,3aS,4S,6aS)-4-((2R,3R)-4-(benzyloxy)-3-(ethanoyloxy)-2-methylbutyl)-3a-hydroxy-1,3-dimethyl-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrol-6a-yl)methyl ethanoate

Synonyms:((3R,3aS,4S,6aS)-4-((2R,3R)-4-(benzyloxy)-3-(ethanoyloxy)-2-methylbutyl)-3a-hydroxy-1,3-dimethyl-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrol-6a-yl)methyl ethanoate

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Chemical Property of ((3R,3aS,4S,6aS)-4-((2R,3R)-4-(benzyloxy)-3-(ethanoyloxy)-2-methylbutyl)-3a-hydroxy-1,3-dimethyl-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrol-6a-yl)methyl ethanoate

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Technology Process of ((3R,3aS,4S,6aS)-4-((2R,3R)-4-(benzyloxy)-3-(ethanoyloxy)-2-methylbutyl)-3a-hydroxy-1,3-dimethyl-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrol-6a-yl)methyl ethanoate

There total 13 articles about ((3R,3aS,4S,6aS)-4-((2R,3R)-4-(benzyloxy)-3-(ethanoyloxy)-2-methylbutyl)-3a-hydroxy-1,3-dimethyl-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrol-6a-yl)methyl ethanoate 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:

: C₂₁H₂₉NO₇

: 108-24-7
acetic anhydride

: 1352406-02-0
((3R,3aS,4S,6aS)-4-((2R,3R)-4-(benzyloxy)-3-(ethanoyloxy)-2-methylbutyl)-3a-hydroxy-1,3-dimethyl-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrol-6a-yl)methyl ethanoate

Guidance literature:: With pyridine; at 20 ℃; for 16h;
DOI:10.1016/j.tet.2011.09.037

Reference yield:

: 1352405-61-8
(3S,7aR)-methyl 7-((3R,4R,1E)-5-(benzyloxy)-4-hydroxy-3-methylpent-1-enyl)-3-tert-butyl-6-methyl-5-oxo-1,3,5,7a-tetrahydropyrrolo[1,2-c]oxazole-7a-carboxylate

: 1352406-02-0
((3R,3aS,4S,6aS)-4-((2R,3R)-4-(benzyloxy)-3-(ethanoyloxy)-2-methylbutyl)-3a-hydroxy-1,3-dimethyl-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrol-6a-yl)methyl ethanoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: sodium acetate; toluene-4-sulfonic acid hydrazide / 1,2-dimethoxyethane; water / Reflux

2.1: 2,6-dimethylpyridine / dichloromethane / 0.67 h / -10 °C

3.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.75 h / -78 °C

4.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / tert-butyl alcohol / 144 h / 20 °C / Darkness

4.2: 12 h / 20 °C

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / chloroform / 24 h / 20 °C

6.1: 1.3-propanedithiol; hydrogenchloride / 2,2,2-trifluoroethanol / 0.75 h / 20 °C

7.1: 2,6-dimethylpyridine / N,N-dimethyl-formamide / 2 h / -10 °C

8.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 20 h / 0 - 20 °C

8.2: 0.5 h / -78 °C

9.1: pyridine / 16 h / 20 °C

With pyridine; 2,6-dimethylpyridine; 1.3-propanedithiol; hydrogenchloride; osmium(VIII) oxide; trimethylsilyl trifluoromethanesulfonate; water; sodium acetate; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; toluene-4-sulfonic acid hydrazide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; chloroform; 2,2,2-trifluoroethanol; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1016/j.tet.2011.09.037

Reference yield:

: 1352405-63-0
(2R,3R)-1-(menzyloxy)-3-methyl-5-(tri-n-butylstannyl)-4-penten-2-ol

: 1352406-02-0
((3R,3aS,4S,6aS)-4-((2R,3R)-4-(benzyloxy)-3-(ethanoyloxy)-2-methylbutyl)-3a-hydroxy-1,3-dimethyl-2,6-dioxohexahydro-1H-furo[3,4-b]pyrrol-6a-yl)methyl ethanoate

Guidance literature:: Multi-step reaction with 10 steps

1.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane / N,N-dimethyl-formamide / 0.08 h / 20 °C

1.2: 15 h / 50 °C

2.1: sodium acetate; toluene-4-sulfonic acid hydrazide / 1,2-dimethoxyethane; water / Reflux

3.1: 2,6-dimethylpyridine / dichloromethane / 0.67 h / -10 °C

4.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.75 h / -78 °C

5.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / tert-butyl alcohol / 144 h / 20 °C / Darkness

5.2: 12 h / 20 °C

6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / chloroform / 24 h / 20 °C

7.1: 1.3-propanedithiol; hydrogenchloride / 2,2,2-trifluoroethanol / 0.75 h / 20 °C

8.1: 2,6-dimethylpyridine / N,N-dimethyl-formamide / 2 h / -10 °C

9.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 20 h / 0 - 20 °C

9.2: 0.5 h / -78 °C

10.1: pyridine / 16 h / 20 °C

With pyridine; 2,6-dimethylpyridine; 1.3-propanedithiol; hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; osmium(VIII) oxide; trifuran-2-yl-phosphane; trimethylsilyl trifluoromethanesulfonate; water; sodium acetate; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; toluene-4-sulfonic acid hydrazide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; chloroform; 2,2,2-trifluoroethanol; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.1: Stille coupling;
DOI:10.1016/j.tet.2011.09.037