(3S,6S,7aR,E)-methyl 7-((3R,4R)-5-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-methylpentylidene)-3-tert-butyl-6-methyl-5-oxohexahydropyrrolo[1,2-c]oxazole-7a-carboxylate

Base Information

Chemical Name:(3S,6S,7aR,E)-methyl 7-((3R,4R)-5-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-methylpentylidene)-3-tert-butyl-6-methyl-5-oxohexahydropyrrolo[1,2-c]oxazole-7a-carboxylate
CAS No.:1352405-59-4
Molecular Formula:C₃₂H₅₁NO₆Si
Molecular Weight:573.846
Hs Code.:

(3S,6S,7aR,E)-methyl 7-((3R,4R)-5-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-methylpentylidene)-3-tert-butyl-6-methyl-5-oxohexahydropyrrolo[1,2-c]oxazole-7a-carboxylate

Synonyms:(3S,6S,7aR,E)-methyl 7-((3R,4R)-5-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-methylpentylidene)-3-tert-butyl-6-methyl-5-oxohexahydropyrrolo[1,2-c]oxazole-7a-carboxylate

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Chemical Property of (3S,6S,7aR,E)-methyl 7-((3R,4R)-5-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-methylpentylidene)-3-tert-butyl-6-methyl-5-oxohexahydropyrrolo[1,2-c]oxazole-7a-carboxylate

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Technology Process of (3S,6S,7aR,E)-methyl 7-((3R,4R)-5-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-methylpentylidene)-3-tert-butyl-6-methyl-5-oxohexahydropyrrolo[1,2-c]oxazole-7a-carboxylate

There total 10 articles about (3S,6S,7aR,E)-methyl 7-((3R,4R)-5-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-methylpentylidene)-3-tert-butyl-6-methyl-5-oxohexahydropyrrolo[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: 50.0%

: 1352405-87-8
(3S,7aR)-methyl 7-((3R,4R)-5-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-methylpentyl)-3-tert-butyl-6-methyl-5-oxo-1,3,5,7a-tetrahydropyrrolo[1,2-c]oxazole-7a-carboxylate

: 1352405-59-4
(3S,6S,7aR,E)-methyl 7-((3R,4R)-5-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-methylpentylidene)-3-tert-butyl-6-methyl-5-oxohexahydropyrrolo[1,2-c]oxazole-7a-carboxylate

: 1352405-68-5
(3S,6R,7aR,E)-methyl 7-((3R,4R)-5-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-methylpentylidene)-3-tert-butyl-6-methyl-5-oxohexahydropyrrolo[1,2-c]oxazole-7a-carboxylate

Guidance literature:: (3S,7aR)-methyl 7-((3R,4R)-5-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-methylpentyl)-3-tert-butyl-6-methyl-5-oxo-1,3,5,7a-tetrahydropyrrolo[1,2-c]oxazole-7a-carboxylate; With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -78 ℃; for 0.75h;

With water; In tetrahydrofuran; toluene; optical yield given as %de; diastereoselective reaction;
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

: 1352405-59-4
(3S,6S,7aR,E)-methyl 7-((3R,4R)-5-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-methylpentylidene)-3-tert-butyl-6-methyl-5-oxohexahydropyrrolo[1,2-c]oxazole-7a-carboxylate

: 1352405-68-5
(3S,6R,7aR,E)-methyl 7-((3R,4R)-5-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-methylpentylidene)-3-tert-butyl-6-methyl-5-oxohexahydropyrrolo[1,2-c]oxazole-7a-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

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

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

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

With 2,6-dimethylpyridine; sodium acetate; potassium hexamethylsilazane; toluene-4-sulfonic acid hydrazide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; toluene;
DOI:10.1016/j.tet.2011.09.037

Reference yield:

: 1352405-72-1
C₁₃H₁₉NO₅

: 1352405-59-4
(3S,6S,7aR,E)-methyl 7-((3R,4R)-5-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-methylpentylidene)-3-tert-butyl-6-methyl-5-oxohexahydropyrrolo[1,2-c]oxazole-7a-carboxylate

: 1352405-68-5
(3S,6R,7aR,E)-methyl 7-((3R,4R)-5-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-3-methylpentylidene)-3-tert-butyl-6-methyl-5-oxohexahydropyrrolo[1,2-c]oxazole-7a-carboxylate

Guidance literature:: Multi-step reaction with 5 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

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

4.1: 2,6-dimethylpyridine / dichloromethane / 0.67 h / -10 °C

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

With 2,6-dimethylpyridine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; sodium acetate; potassium hexamethylsilazane; N-ethyl-N,N-diisopropylamine; toluene-4-sulfonic acid hydrazide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 2.1: Stille coupling;
DOI:10.1016/j.tet.2011.09.037