(E)-4-[(2R,3R,5S)-5-[(1R,2R,3R)-2,5-Bis-methoxymethoxy-3-methyl-1-(2-trimethylsilanyl-ethoxymethoxy)-pentyl]-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-but-3-en-2-one

Base Information

Chemical Name:(E)-4-[(2R,3R,5S)-5-[(1R,2R,3R)-2,5-Bis-methoxymethoxy-3-methyl-1-(2-trimethylsilanyl-ethoxymethoxy)-pentyl]-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-but-3-en-2-one
CAS No.:413598-69-3
Molecular Formula:C₃₂H₅₄O₁₀Si
Molecular Weight:626.86
Hs Code.:

(E)-4-[(2R,3R,5S)-5-[(1R,2R,3R)-2,5-Bis-methoxymethoxy-3-methyl-1-(2-trimethylsilanyl-ethoxymethoxy)-pentyl]-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-but-3-en-2-one

Synonyms:(E)-4-[(2R,3R,5S)-5-[(1R,2R,3R)-2,5-Bis-methoxymethoxy-3-methyl-1-(2-trimethylsilanyl-ethoxymethoxy)-pentyl]-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-but-3-en-2-one

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Chemical Property of (E)-4-[(2R,3R,5S)-5-[(1R,2R,3R)-2,5-Bis-methoxymethoxy-3-methyl-1-(2-trimethylsilanyl-ethoxymethoxy)-pentyl]-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-but-3-en-2-one

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Technology Process of (E)-4-[(2R,3R,5S)-5-[(1R,2R,3R)-2,5-Bis-methoxymethoxy-3-methyl-1-(2-trimethylsilanyl-ethoxymethoxy)-pentyl]-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-but-3-en-2-one

There total 19 articles about (E)-4-[(2R,3R,5S)-5-[(1R,2R,3R)-2,5-Bis-methoxymethoxy-3-methyl-1-(2-trimethylsilanyl-ethoxymethoxy)-pentyl]-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-but-3-en-2-one 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: 86.0%

: 1067-71-6
Diethyl (2-oxopropyl)phosphonate

: 413598-68-2
(2S,3R,5S)-5-[(1R,2R,3R)-2,5-Bis-methoxymethoxy-3-methyl-1-(2-trimethylsilanyl-ethoxymethoxy)-pentyl]-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carbaldehyde

: 413598-69-3
(E)-4-[(2R,3R,5S)-5-[(1R,2R,3R)-2,5-Bis-methoxymethoxy-3-methyl-1-(2-trimethylsilanyl-ethoxymethoxy)-pentyl]-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-but-3-en-2-one

Guidance literature:: With sodium hydride; In tetrahydrofuran; at 0 ℃;
DOI:10.1021/ol010302l

Reference yield:

: 413598-52-4
(E)-(2R,3S)-3-Methoxymethoxy-2-methyl-hex-4-en-1-ol

: 413598-69-3
(E)-4-[(2R,3R,5S)-5-[(1R,2R,3R)-2,5-Bis-methoxymethoxy-3-methyl-1-(2-trimethylsilanyl-ethoxymethoxy)-pentyl]-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-but-3-en-2-one

Guidance literature:: Multi-step reaction with 14 steps

1.1: 97 percent / DMAP; pyridine

2.1: 77 percent / dimethylformamide / 90 °C

3.1: DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

4.1: 1.180 g / NaBH₄ / methanol / 0.5 h / 0 °C

5.1: 100 percent / (i-Pr)2NEt / CH₂Cl₂ / -78 - 20 °C

6.1: O₃ / CH₂Cl₂ / -78 °C

6.2: 92 percent / PPh₃ / CH₂Cl₂ / -78 - 20 °C

7.1: 52 percent / t-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C

8.1: 85 percent / (i-Pr)2NEt / CH₂Cl₂ / 0 - 20 °C

9.1: 66 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

10.1: 68 percent / [Rh(NBD)(DIPHOS-4)]BF₄; NaH / tetrahydrofuran / 72 h / 20 °C / 41372.9 - 46544.6 Torr

11.1: 93 percent / NaH / dimethylformamide / 4 h / 20 °C

12.1: 100 percent / aq. AcOH / 4.5 h / 20 °C

13.1: 100 percent / NaIO₄; SiO₂ / CH₂Cl₂ / 1 h / 20 °C

14.1: 86 percent / NaH / tetrahydrofuran / 0.25 h / 0 °C

With pyridine; dmap; sodium tetrahydroborate; sodium periodate; norborna-2,5-diene(1,2-bis(diphenylphosphino)ethane)rhodium(I) tetrafluoroborate; tetrabutyl ammonium fluoride; tert.-butyl lithium; silica gel; sodium hydride; diisobutylaluminium hydride; ozone; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1016/j.tet.2004.06.142

Reference yield:

: 413598-54-6
(E)-(3R,4R)-4-Methoxymethoxy-3-methyl-hept-5-en-1-ol

: 413598-69-3
(E)-4-[(2R,3R,5S)-5-[(1R,2R,3R)-2,5-Bis-methoxymethoxy-3-methyl-1-(2-trimethylsilanyl-ethoxymethoxy)-pentyl]-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-but-3-en-2-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: 100 percent / (i-Pr)2NEt / CH₂Cl₂ / -78 - 20 °C

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: 92 percent / PPh₃ / CH₂Cl₂ / -78 - 20 °C

3.1: 52 percent / t-BuLi / tetrahydrofuran; pentane / 0.5 h / -78 °C

4.1: 85 percent / (i-Pr)2NEt / CH₂Cl₂ / 0 - 20 °C

5.1: 66 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

6.1: 68 percent / [Rh(NBD)(DIPHOS-4)]BF₄; NaH / tetrahydrofuran / 72 h / 20 °C / 41372.9 - 46544.6 Torr

7.1: 93 percent / NaH / dimethylformamide / 4 h / 20 °C

8.1: 100 percent / aq. AcOH / 4.5 h / 20 °C

9.1: 100 percent / NaIO₄; SiO₂ / CH₂Cl₂ / 1 h / 20 °C

10.1: 86 percent / NaH / tetrahydrofuran / 0.25 h / 0 °C

With sodium periodate; norborna-2,5-diene(1,2-bis(diphenylphosphino)ethane)rhodium(I) tetrafluoroborate; tetrabutyl ammonium fluoride; tert.-butyl lithium; silica gel; sodium hydride; ozone; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; pentane;
DOI:10.1016/j.tet.2004.06.142