[(1R,2R,3R)-1-{(2S,5S)-5-[(E)-4-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-enyl]-tetrahydro-furan-2-yl}-2-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyloxy]-triethyl-silane

Base Information

Chemical Name:[(1R,2R,3R)-1-{(2S,5S)-5-[(E)-4-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-enyl]-tetrahydro-furan-2-yl}-2-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyloxy]-triethyl-silane
CAS No.:921763-76-0
Molecular Formula:C₃₆H₅₆O₆Si
Molecular Weight:612.923
Hs Code.:

[(1R,2R,3R)-1-{(2S,5S)-5-[(E)-4-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-enyl]-tetrahydro-furan-2-yl}-2-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyloxy]-triethyl-silane

Synonyms:[(1R,2R,3R)-1-{(2S,5S)-5-[(E)-4-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-enyl]-tetrahydro-furan-2-yl}-2-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyloxy]-triethyl-silane

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Chemical Property of [(1R,2R,3R)-1-{(2S,5S)-5-[(E)-4-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-enyl]-tetrahydro-furan-2-yl}-2-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyloxy]-triethyl-silane

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Technology Process of [(1R,2R,3R)-1-{(2S,5S)-5-[(E)-4-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-enyl]-tetrahydro-furan-2-yl}-2-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyloxy]-triethyl-silane

There total 17 articles about [(1R,2R,3R)-1-{(2S,5S)-5-[(E)-4-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-enyl]-tetrahydro-furan-2-yl}-2-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyloxy]-triethyl-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: 94.0%

: 921763-75-9
(1R,2R,3R)-1-{(2S,5S)-5-[(E)-4-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-enyl]-tetrahydro-furan-2-yl}-2-(4-methoxy-benzyloxy)-3-methyl-hex-5-yn-1-ol

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 921763-76-0
[(1R,2R,3R)-1-{(2S,5S)-5-[(E)-4-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-enyl]-tetrahydro-furan-2-yl}-2-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyloxy]-triethyl-silane

Guidance literature:: With triethylamine; In dichloromethane; at 0 ℃; for 0.0833333h;
DOI:10.1021/ja066663j

Reference yield:

: 921763-53-3
(E)-5-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-pent-4-enal

: 921763-76-0
[(1R,2R,3R)-1-{(2S,5S)-5-[(E)-4-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-enyl]-tetrahydro-furan-2-yl}-2-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyloxy]-triethyl-silane

Guidance literature:: Multi-step reaction with 3 steps

1: 48 percent / 4 Angstroem molecular sieves; BF₃*OEt₂ / CH₂Cl₂ / 21 h / -78 °C

2: 85 percent / TBAF*3H₂O / dimethylformamide / 72 h / Heating

3: 94 percent / Et₃N / CH₂Cl₂ / 0.08 h / 0 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; triethylamine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja066663j

Reference yield:

: 1-((4R,5R)-2,2-Dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-prop-2-en-1-ol

: 921763-76-0
[(1R,2R,3R)-1-{(2S,5S)-5-[(E)-4-((4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-enyl]-tetrahydro-furan-2-yl}-2-(4-methoxy-benzyloxy)-3-methyl-hex-5-ynyloxy]-triethyl-silane

Guidance literature:: Multi-step reaction with 5 steps

1: 2.83 g / propionic acid / toluene / 18 h / Heating

2: 81 percent / DIBAL / toluene; hexane / 0.5 h / -78 °C

3: 48 percent / 4 Angstroem molecular sieves; BF₃*OEt₂ / CH₂Cl₂ / 21 h / -78 °C

4: 85 percent / TBAF*3H₂O / dimethylformamide / 72 h / Heating

5: 94 percent / Et₃N / CH₂Cl₂ / 0.08 h / 0 °C

With 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; propionic acid; triethylamine; In hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 1: Claisen rearrangement;
DOI:10.1021/ja066663j