(S)-1-[(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]-ethane-1,2-diol

Base Information

Chemical Name:(S)-1-[(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]-ethane-1,2-diol
CAS No.:794515-82-5
Molecular Formula:C₃₀H₅₄O₁₁Si
Molecular Weight:618.838
Hs Code.:

(S)-1-[(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]-ethane-1,2-diol

Synonyms:(S)-1-[(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]-ethane-1,2-diol

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Chemical Property of (S)-1-[(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]-ethane-1,2-diol

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Technology Process of (S)-1-[(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]-ethane-1,2-diol

There total 17 articles about (S)-1-[(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]-ethane-1,2-diol 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: 100.0%

: 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

: 794515-82-5
(S)-1-[(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]-ethane-1,2-diol

Guidance literature:: With acetic acid; at 20 ℃; for 4.5h;
DOI:10.1016/j.tet.2004.06.142

Reference yield:

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

: 794515-82-5
(S)-1-[(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]-ethane-1,2-diol

Guidance literature:: Multi-step reaction with 12 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

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; 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

: 794515-82-5
(S)-1-[(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]-ethane-1,2-diol

Guidance literature:: Multi-step reaction with 8 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

With norborna-2,5-diene(1,2-bis(diphenylphosphino)ethane)rhodium(I) tetrafluoroborate; tetrabutyl ammonium fluoride; tert.-butyl lithium; 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