(E)-tert-butyl 3-phenyl-3-((1S,2S,5S)-1,2,5-tribenzyl-4-oxo-3,6-dioxabicyclo[3.1.0]hexan-2-yl)acrylate

Base Information

Chemical Name:(E)-tert-butyl 3-phenyl-3-((1S,2S,5S)-1,2,5-tribenzyl-4-oxo-3,6-dioxabicyclo[3.1.0]hexan-2-yl)acrylate
CAS No.:1610527-74-6
Molecular Formula:C₃₈H₃₆O₅
Molecular Weight:572.701
Hs Code.:

Synonyms:(E)-tert-butyl 3-phenyl-3-((1S,2S,5S)-1,2,5-tribenzyl-4-oxo-3,6-dioxabicyclo[3.1.0]hexan-2-yl)acrylate

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Chemical Property of (E)-tert-butyl 3-phenyl-3-((1S,2S,5S)-1,2,5-tribenzyl-4-oxo-3,6-dioxabicyclo[3.1.0]hexan-2-yl)acrylate

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Technology Process of (E)-tert-butyl 3-phenyl-3-((1S,2S,5S)-1,2,5-tribenzyl-4-oxo-3,6-dioxabicyclo[3.1.0]hexan-2-yl)acrylate

There total 8 articles about (E)-tert-butyl 3-phenyl-3-((1S,2S,5S)-1,2,5-tribenzyl-4-oxo-3,6-dioxabicyclo[3.1.0]hexan-2-yl)acrylate 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: 94.0%

: 1610527-73-5
(1S,4R,5S)-4-benzoyl-1,4,5-tribenzyl-3,6-dioxabicyclo[3.1.0]hexan-2-one

: 103230-42-8
3,3-dimethyl-1-(trimethylsilyl)-butan-2-one

: 1610527-74-6
(E)-tert-butyl 3-phenyl-3-((1S,2S,5S)-1,2,5-tribenzyl-4-oxo-3,6-dioxabicyclo[3.1.0]hexan-2-yl)acrylate

Guidance literature:: 3,3-dimethyl-1-(trimethylsilyl)-butan-2-one; With n-butyllithium; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

(1S,4R,5S)-4-benzoyl-1,4,5-tribenzyl-3,6-dioxabicyclo[3.1.0]hexan-2-one; In tetrahydrofuran; hexane; at -78 ℃; for 2h;
DOI:10.1002/anie.201307835

Reference yield:

: 1610527-72-4
(1S,4S,5S)-1,4,5-tribenzyl-4-(hydroxy(phenyl)methyl)-3,6-dioxabicyclo[3.1.0]hexan-2-one

: 1610527-74-6
(E)-tert-butyl 3-phenyl-3-((1S,2S,5S)-1,2,5-tribenzyl-4-oxo-3,6-dioxabicyclo[3.1.0]hexan-2-yl)acrylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 4 h / 0 - 20 °C

2.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C

2.2: 0.5 h / -78 °C

2.3: 2 h / -78 °C

With n-butyllithium; sodium hydrogencarbonate; Dess-Martin periodane; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; dichloromethane; 2.1: |Peterson Olefination;
DOI:10.1002/anie.201307835

Reference yield:

: C₂₆H₂₂O₄

: 1610527-74-6
(E)-tert-butyl 3-phenyl-3-((1S,2S,5S)-1,2,5-tribenzyl-4-oxo-3,6-dioxabicyclo[3.1.0]hexan-2-yl)acrylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrahydrofuran / 14 h / -40 °C

2.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 4 h / 0 - 20 °C

3.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C

3.2: 0.5 h / -78 °C

3.3: 2 h / -78 °C

With n-butyllithium; sodium hydrogencarbonate; Dess-Martin periodane; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; dichloromethane; 1.1: |Grignard Reaction / 3.1: |Peterson Olefination;
DOI:10.1002/anie.201307835