(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

Base Information

Chemical Name:(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
CAS No.:1352405-61-8
Molecular Formula:C₂₆H₃₅NO₆
Molecular Weight:457.567
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 4 articles about (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 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:

: 1352405-72-1
C₁₃H₁₉NO₅

: 1352405-65-2
(3S,7aR)-methyl 7-((3R,4R,1Z)-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

: 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

Guidance literature:: Multi-step reaction with 2 steps

1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / 50 °C

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

2.2: 15 h / 50 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; 2.1: Stille coupling;
DOI:10.1016/j.tet.2011.09.037

Reference yield:

: C₁₅H₂₅NO₆

: 1352405-65-2
(3S,7aR)-methyl 7-((3R,4R,1Z)-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

: 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

Guidance literature:: Multi-step reaction with 3 steps

1.1: potassium tert-butylate / tert-butyl alcohol / Heating

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / 50 °C

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

3.2: 15 h / 50 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; potassium tert-butylate; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Dieckmann reaction / 3.1: Stille coupling;
DOI:10.1016/j.tet.2011.09.037

Reference yield:

: 257291-68-2
methyl (R)-2-tert-butyloxazolidine-4-carboxylate

: 1352405-65-2
(3S,7aR)-methyl 7-((3R,4R,1Z)-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

: 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

Guidance literature:: Multi-step reaction with 4 steps

1.1: pyridine / dichloromethane / 20 °C

2.1: potassium tert-butylate / tert-butyl alcohol / Heating

3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / 50 °C

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

4.2: 15 h / 50 °C

With pyridine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; potassium tert-butylate; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 2.1: Dieckmann reaction / 4.1: Stille coupling;
DOI:10.1016/j.tet.2011.09.037