ethyl (4S,5S,E)-5-azido-4-((tert-butyldimethylsilyl)oxy)-5-phenylpent-2-enoate

Base Information

Chemical Name:ethyl (4S,5S,E)-5-azido-4-((tert-butyldimethylsilyl)oxy)-5-phenylpent-2-enoate
CAS No.:1609543-94-3
Molecular Formula:C₁₉H₂₉N₃O₃Si
Molecular Weight:375.543
Hs Code.:

Synonyms:ethyl (4S,5S,E)-5-azido-4-((tert-butyldimethylsilyl)oxy)-5-phenylpent-2-enoate

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Chemical Property of ethyl (4S,5S,E)-5-azido-4-((tert-butyldimethylsilyl)oxy)-5-phenylpent-2-enoate

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Technology Process of ethyl (4S,5S,E)-5-azido-4-((tert-butyldimethylsilyl)oxy)-5-phenylpent-2-enoate

There total 3 articles about ethyl (4S,5S,E)-5-azido-4-((tert-butyldimethylsilyl)oxy)-5-phenylpent-2-enoate 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:

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: 1609543-93-2
(2R,3S)-3-azido-2-((tert-butyldimethylsilyl)oxy)-3-phenylpropanal

: 1609543-94-3
ethyl (4S,5S,E)-5-azido-4-((tert-butyldimethylsilyl)oxy)-5-phenylpent-2-enoate

Guidance literature:: diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.0833333h;

(2R,3S)-3-azido-2-((tert-butyldimethylsilyl)oxy)-3-phenylpropanal; In tetrahydrofuran; at 25 ℃; for 3h;
DOI:10.1055/s-0033-1340074

Reference yield:

: 1609543-92-1
(2R,3S)-3-azido-2-((tert-butyldimethylsilyl)oxy)-3-phenylpropan-1-ol

: 1609543-94-3
ethyl (4S,5S,E)-5-azido-4-((tert-butyldimethylsilyl)oxy)-5-phenylpent-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: Dess-Martin periodane / dichloromethane / 1 h / 25 °C

2.1: sodium hydride / tetrahydrofuran / 0.08 h / 0 °C

2.2: 3 h / 25 °C

With sodium hydride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 1.1: |Dess-Martin Oxidation / 2.2: |Wittig-Horner Reaction;
DOI:10.1055/s-0033-1340074

Reference yield:

: 1609543-90-9
C₂₁H₃₉N₃O₂Si₂

: 1609543-94-3
ethyl (4S,5S,E)-5-azido-4-((tert-butyldimethylsilyl)oxy)-5-phenylpent-2-enoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: camphor-10-sulfonic acid / methanol / 6 h / 0 °C

2.1: Dess-Martin periodane / dichloromethane / 1 h / 25 °C

3.1: sodium hydride / tetrahydrofuran / 0.08 h / 0 °C

3.2: 3 h / 25 °C

With camphor-10-sulfonic acid; sodium hydride; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane; 2.1: |Dess-Martin Oxidation / 3.2: |Wittig-Horner Reaction;
DOI:10.1055/s-0033-1340074