ethyl (2E)-3-[(2R,3S,4R)-1-benzyloxycarbonyl-4-benzyloxy-3-hydroxypiperidin-2-yl]prop-2-enoate

Base Information

Chemical Name:ethyl (2E)-3-[(2R,3S,4R)-1-benzyloxycarbonyl-4-benzyloxy-3-hydroxypiperidin-2-yl]prop-2-enoate
CAS No.:1447810-39-0
Molecular Formula:C₂₅H₂₉NO₆
Molecular Weight:439.508
Hs Code.:

Synonyms:ethyl (2E)-3-[(2R,3S,4R)-1-benzyloxycarbonyl-4-benzyloxy-3-hydroxypiperidin-2-yl]prop-2-enoate

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Chemical Property of ethyl (2E)-3-[(2R,3S,4R)-1-benzyloxycarbonyl-4-benzyloxy-3-hydroxypiperidin-2-yl]prop-2-enoate

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Technology Process of ethyl (2E)-3-[(2R,3S,4R)-1-benzyloxycarbonyl-4-benzyloxy-3-hydroxypiperidin-2-yl]prop-2-enoate

There total 7 articles about ethyl (2E)-3-[(2R,3S,4R)-1-benzyloxycarbonyl-4-benzyloxy-3-hydroxypiperidin-2-yl]prop-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: 48.0%

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

: 1447810-36-7
C₂₁H₂₃NO₅

: 1447810-39-0
ethyl (2E)-3-[(2R,3S,4R)-1-benzyloxycarbonyl-4-benzyloxy-3-hydroxypiperidin-2-yl]prop-2-enoate

Guidance literature:: diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; mineral oil; at -40 ℃; for 0.166667h;

C₂₁H₂₃NO₅; In tetrahydrofuran; mineral oil; at -40 - -20 ℃; for 5.16667h;
DOI:10.1021/jo400448p

Reference yield:

: 1447810-30-1
(1R)-1-[(3aR,5S,6S,6aR)-6-azido-2,2-dimethyltetrahydrofuro-[2,3-d][1,3]dioxol-5-yl]but-3-en-1-ol

: 1447810-39-0
ethyl (2E)-3-[(2R,3S,4R)-1-benzyloxycarbonyl-4-benzyloxy-3-hydroxypiperidin-2-yl]prop-2-enoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 - 25 °C

1.2: 4 h / 0 - 25 °C

2.1: ozone / dichloromethane / -78 °C

2.2: 12 h / -78 - 25 °C

3.1: sodium hydrogencarbonate / water; methanol / 6 h / 0 - 25 °C

4.1: trifluoroacetic acid / water / 1 h / 0 °C

5.1: sodium periodate / water; acetone / 0.5 h / 0 °C

6.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / -40 °C

6.2: 5.17 h / -40 - -20 °C

With sodium periodate; sodium hydride; sodium hydrogencarbonate; ozone; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; acetone; mineral oil; 6.2: |Wittig-Horner Reaction;
DOI:10.1021/jo400448p

Reference yield:

: 1447810-31-2
(3aR,5S,6S,6aR)-6-azido-5-[(1R)-1-(benzyloxy)but-3-en-1-yl]-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxole

: 1447810-39-0
ethyl (2E)-3-[(2R,3S,4R)-1-benzyloxycarbonyl-4-benzyloxy-3-hydroxypiperidin-2-yl]prop-2-enoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: ozone / dichloromethane / -78 °C

1.2: 12 h / -78 - 25 °C

2.1: sodium hydrogencarbonate / water; methanol / 6 h / 0 - 25 °C

3.1: trifluoroacetic acid / water / 1 h / 0 °C

4.1: sodium periodate / water; acetone / 0.5 h / 0 °C

5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / -40 °C

5.2: 5.17 h / -40 - -20 °C

With sodium periodate; sodium hydride; sodium hydrogencarbonate; ozone; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; acetone; mineral oil; 5.2: |Wittig-Horner Reaction;
DOI:10.1021/jo400448p