3-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-propionaldehyde

Base Information

Chemical Name:3-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-propionaldehyde
CAS No.:474005-66-8
Molecular Formula:C₂₆H₃₄O₃Si
Molecular Weight:422.64
Hs Code.:

Synonyms:3-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-propionaldehyde

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Chemical Property of 3-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-propionaldehyde

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Technology Process of 3-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-propionaldehyde

There total 23 articles about 3-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-propionaldehyde 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%

: 499121-77-6
3-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-propan-1-ol

: 474005-66-8
3-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-propionaldehyde

Guidance literature:: With sodium acetate; In dichloromethane; at 20 ℃; for 3h;
DOI:10.1021/jo026302w

Reference yield: 79.0%

: 474005-75-9
(E)-3-{(2R,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-prop-2-en-1-ol

: 474005-66-8
3-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-propionaldehyde

Guidance literature:: With hydrogen; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; at 0 ℃;
DOI:10.1021/ol026504e

Reference yield:

: 474005-86-2
(E)-3-[(7R,9R)-9-((E)-2-Ethoxycarbonyl-vinyl)-6,10-dioxa-spiro[4.5]dec-7-yl]-acrylic acid ethyl ester

: 474005-66-8
3-{(2S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-methylene-tetrahydro-furan-2-yl}-propionaldehyde

Guidance literature:: Multi-step reaction with 11 steps

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

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

1.3: 81 percent / MgSO₄ / diethyl ether; toluene; methanol

2.1: 94 percent / DMAP; pyridine / CH₂Cl₂ / 0 - 20 °C

3.1: 100 percent / AcOH; H₂O / 2 h

4.1: 87 percent / Pd₂(dba)3*CHCl₃; (R,R)-DPPBA / tetrahydrofuran / 0 °C

5.1: 72 percent / camphorsulfonic acid / CH₂Cl₂ / 0 - 20 °C

6.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 20 °C

6.2: 81 percent / NaBO₃ / tetrahydrofuran; H₂O

7.1: 87 percent / imidazole / dimethylformamide / 20 °C

8.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂ / 20 °C

9.1: 92 percent / 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂ / 20 °C

10.1: n-BuLi / tetrahydrofuran; hexane / 20 °C

10.2: 82 percent / tetrahydrofuran; hexane / -78 - 20 °C

11.1: 79 percent / hydrogen / [Ir(cod)(PPh₂Me)2]PF₆ / tetrahydrofuran / 0 °C

With pyridine; 1H-imidazole; dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; n-butyllithium; (R,R)-DPPBA; camphor-10-sulfonic acid; water; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; 9-bora-bicyclo[3.3.1]nonane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 9.1: Dess-Martin oxidation;
DOI:10.1021/ol026504e