(3S,7aR)-methyl 7-((3R,4R)-5-(benzyloxy)-4-hydroxy-3-methylpentyl)-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)-5-(benzyloxy)-4-hydroxy-3-methylpentyl)-3-tert-butyl-6-methyl-5-oxo-1,3,5,7a-tetrahydropyrrolo[1,2-c]oxazole-7a-carboxylate
CAS No.:1352405-85-6
Molecular Formula:C₂₆H₃₇NO₆
Molecular Weight:459.583
Hs Code.:

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

There total 7 articles about (3S,7aR)-methyl 7-((3R,4R)-5-(benzyloxy)-4-hydroxy-3-methylpentyl)-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: 89.0%

: 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

: 1352405-85-6
(3S,7aR)-methyl 7-((3R,4R)-5-(benzyloxy)-4-hydroxy-3-methylpentyl)-3-tert-butyl-6-methyl-5-oxo-1,3,5,7a-tetrahydropyrrolo[1,2-c]oxazole-7a-carboxylate

Guidance literature:: With sodium acetate; toluene-4-sulfonic acid hydrazide; In 1,2-dimethoxyethane; water; Reflux;
DOI:10.1016/j.tet.2011.09.037

Reference yield:

: 1352405-72-1
C₁₃H₁₉NO₅

: 1352405-85-6
(3S,7aR)-methyl 7-((3R,4R)-5-(benzyloxy)-4-hydroxy-3-methylpentyl)-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: 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

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; sodium acetate; N-ethyl-N,N-diisopropylamine; toluene-4-sulfonic acid hydrazide; In 1,2-dimethoxyethane; dichloromethane; water; N,N-dimethyl-formamide; 2.1: Stille coupling;
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

: 1352405-85-6
(3S,7aR)-methyl 7-((3R,4R)-5-(benzyloxy)-4-hydroxy-3-methylpentyl)-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: 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

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane; sodium acetate; toluene-4-sulfonic acid hydrazide; In 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; 1.1: Stille coupling;
DOI:10.1016/j.tet.2011.09.037