(2-{(1R,2R,3R)-1-[(2S,4R,5S)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,5-bis-methoxymethoxy-3-methyl-pentyloxymethoxy}-ethyl)-trimethyl-silane

Base Information

Chemical Name:(2-{(1R,2R,3R)-1-[(2S,4R,5S)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,5-bis-methoxymethoxy-3-methyl-pentyloxymethoxy}-ethyl)-trimethyl-silane
CAS No.:413598-67-1
Molecular Formula:C₃₃H₅₈O₁₁Si
Molecular Weight:658.902
Hs Code.:

(2-{(1R,2R,3R)-1-[(2S,4R,5S)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,5-bis-methoxymethoxy-3-methyl-pentyloxymethoxy}-ethyl)-trimethyl-silane

Synonyms:(2-{(1R,2R,3R)-1-[(2S,4R,5S)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,5-bis-methoxymethoxy-3-methyl-pentyloxymethoxy}-ethyl)-trimethyl-silane

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Chemical Property of (2-{(1R,2R,3R)-1-[(2S,4R,5S)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,5-bis-methoxymethoxy-3-methyl-pentyloxymethoxy}-ethyl)-trimethyl-silane

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Technology Process of (2-{(1R,2R,3R)-1-[(2S,4R,5S)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,5-bis-methoxymethoxy-3-methyl-pentyloxymethoxy}-ethyl)-trimethyl-silane

There total 15 articles about (2-{(1R,2R,3R)-1-[(2S,4R,5S)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,5-bis-methoxymethoxy-3-methyl-pentyloxymethoxy}-ethyl)-trimethyl-silane 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: 93.0%

: 2746-25-0
p-Methoxybenzyl bromide

: 413598-65-9
(2S,3R,5S)-5-[(1R,2R,3R)-2,5-Bis-methoxymethoxy-3-methyl-1-(2-trimethylsilanyl-ethoxymethoxy)-pentyl]-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-tetrahydro-furan-3-ol

: 413598-67-1
(2-{(1R,2R,3R)-1-[(2S,4R,5S)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,5-bis-methoxymethoxy-3-methyl-pentyloxymethoxy}-ethyl)-trimethyl-silane

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1021/ol010302l

Reference yield:

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

: 413598-67-1
(2-{(1R,2R,3R)-1-[(2S,4R,5S)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,5-bis-methoxymethoxy-3-methyl-pentyloxymethoxy}-ethyl)-trimethyl-silane

Guidance literature:: Multi-step reaction with 11 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

With pyridine; dmap; sodium tetrahydroborate; norborna-2,5-diene(1,2-bis(diphenylphosphino)ethane)rhodium(I) tetrafluoroborate; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; ozone; 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

: 413598-67-1
(2-{(1R,2R,3R)-1-[(2S,4R,5S)-5-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2,5-bis-methoxymethoxy-3-methyl-pentyloxymethoxy}-ethyl)-trimethyl-silane

Guidance literature:: Multi-step reaction with 7 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

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