Acetic acid (E)-3-[(2R,4R,5S)-5-(2-hydroxy-ethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-allyl ester

Base Information

Chemical Name:Acetic acid (E)-3-[(2R,4R,5S)-5-(2-hydroxy-ethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-allyl ester
CAS No.:474005-73-7
Molecular Formula:C₁₉H₂₆O₆
Molecular Weight:350.412
Hs Code.:

Synonyms:Acetic acid (E)-3-[(2R,4R,5S)-5-(2-hydroxy-ethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-allyl ester

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Chemical Property of Acetic acid (E)-3-[(2R,4R,5S)-5-(2-hydroxy-ethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-allyl ester

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Technology Process of Acetic acid (E)-3-[(2R,4R,5S)-5-(2-hydroxy-ethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-allyl ester

There total 8 articles about Acetic acid (E)-3-[(2R,4R,5S)-5-(2-hydroxy-ethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-allyl ester 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: 81.0%

: 474005-72-6
Acetic acid (E)-3-[(2R,4R,5S)-4-(4-methoxy-benzyloxy)-5-vinyl-tetrahydro-furan-2-yl]-allyl ester

: 474005-73-7
Acetic acid (E)-3-[(2R,4R,5S)-5-(2-hydroxy-ethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-allyl ester

Guidance literature:: Acetic acid (E)-3-[(2R,4R,5S)-4-(4-methoxy-benzyloxy)-5-vinyl-tetrahydro-furan-2-yl]-allyl ester; With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; at 20 ℃;

With sodium perborate; In tetrahydrofuran; water; Further stages.;
DOI:10.1021/ol026504e

Reference yield:

: 474005-85-1
(7R,9R)-7,9-Divinyl-6,10-dioxa-spiro[4.5]decane

: 474005-73-7
Acetic acid (E)-3-[(2R,4R,5S)-5-(2-hydroxy-ethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-allyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: ozone / CH₂Cl₂ / -78 °C

1.2: PPh₃ / CH₂Cl₂ / -20 °C

1.3: 85 percent / NaH / tetrahydrofuran; CH₂Cl₂ / -78 °C

2.1: DIBAL / diethyl ether; toluene / -78 - 0 °C

2.2: Rochelle's salt / diethyl ether; toluene; methanol

2.3: 81 percent / MgSO₄ / diethyl ether; toluene; methanol

3.1: 94 percent / DMAP; pyridine / CH₂Cl₂ / 0 - 20 °C

4.1: 100 percent / AcOH; H₂O / 2 h

5.1: 87 percent / Pd₂(dba)3*CHCl₃; (R,R)-DPPBA / tetrahydrofuran / 0 °C

6.1: 72 percent / camphorsulfonic acid / CH₂Cl₂ / 0 - 20 °C

7.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 20 °C

7.2: 81 percent / NaBO₃ / tetrahydrofuran; H₂O

With pyridine; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (R,R)-DPPBA; camphor-10-sulfonic acid; water; diisobutylaluminium hydride; ozone; acetic acid; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ol026504e

Reference yield:

: 474005-87-3
(E)-3-[(7R,9R)-9-((E)-3-Hydroxy-propenyl)-6,10-dioxa-spiro[4.5]dec-7-yl]-prop-2-en-1-ol

: 474005-73-7
Acetic acid (E)-3-[(2R,4R,5S)-5-(2-hydroxy-ethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-allyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 94 percent / DMAP; pyridine / CH₂Cl₂ / 0 - 20 °C

2.1: 100 percent / AcOH; H₂O / 2 h

3.1: 87 percent / Pd₂(dba)3*CHCl₃; (R,R)-DPPBA / tetrahydrofuran / 0 °C

4.1: 72 percent / camphorsulfonic acid / CH₂Cl₂ / 0 - 20 °C

5.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 20 °C

5.2: 81 percent / NaBO₃ / tetrahydrofuran; H₂O

With pyridine; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (R,R)-DPPBA; camphor-10-sulfonic acid; water; acetic acid; 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol026504e