{(E)-(R)-1-allyl-4-[(4S,6S)-2,2-dimethyl-6-phenethyl-[1,3]dioxan-4-yl]-but-2-enyloxy}-tert-butyldimethylsilane

Base Information

Chemical Name:{(E)-(R)-1-allyl-4-[(4S,6S)-2,2-dimethyl-6-phenethyl-[1,3]dioxan-4-yl]-but-2-enyloxy}-tert-butyldimethylsilane
CAS No.:745058-49-5
Molecular Formula:C₂₇H₄₄O₃Si
Molecular Weight:444.73
Hs Code.:

Synonyms:{(E)-(R)-1-allyl-4-[(4S,6S)-2,2-dimethyl-6-phenethyl-[1,3]dioxan-4-yl]-but-2-enyloxy}-tert-butyldimethylsilane

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Chemical Property of {(E)-(R)-1-allyl-4-[(4S,6S)-2,2-dimethyl-6-phenethyl-[1,3]dioxan-4-yl]-but-2-enyloxy}-tert-butyldimethylsilane

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Technology Process of {(E)-(R)-1-allyl-4-[(4S,6S)-2,2-dimethyl-6-phenethyl-[1,3]dioxan-4-yl]-but-2-enyloxy}-tert-butyldimethylsilane

There total 13 articles about {(E)-(R)-1-allyl-4-[(4S,6S)-2,2-dimethyl-6-phenethyl-[1,3]dioxan-4-yl]-but-2-enyloxy}-tert-butyldimethylsilane 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: 69.0%

: 485321-85-5
5-{2-[(4R,6S)-2,2-dimethyl-6-phenethyl-[1,3]dioxan-4-yl]-ethylsulfonyl}-1-phenyl-1H-tetrazole

: 745058-24-6
(R)-2-(tert-butyldimethylsilanyloxy)-pent-4-enal

: 745058-49-5
{(E)-(R)-1-allyl-4-[(4S,6S)-2,2-dimethyl-6-phenethyl-[1,3]dioxan-4-yl]-but-2-enyloxy}-tert-butyldimethylsilane

Guidance literature:: With potassium hexamethylsilazane; In 1,2-dimethoxyethane; toluene; at -65 - 20 ℃;
DOI:10.1055/s-2004-822387

Reference yield:

: 2100-17-6
4-pentenal

: 745058-49-5
{(E)-(R)-1-allyl-4-[(4S,6S)-2,2-dimethyl-6-phenethyl-[1,3]dioxan-4-yl]-but-2-enyloxy}-tert-butyldimethylsilane

Guidance literature:: Multi-step reaction with 7 steps

1: (S)-proline / CHCl₃ / 0.42 h / 0 °C

2: 0.883 g / NaBH₄ / methanol / 0.33 h / 0 °C

3: SmI₂ / tetrahydrofuran / 2.25 h

4: 91 percent / imidazole / dimethylformamide / 20 °C

5: 57 percent / pyridine; HF*pyridine / tetrahydrofuran / 24 h / 20 °C

6: 98 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.67 h / -78 - 0 °C

7: 69 percent / KHMDS / 1,2-dimethoxy-ethane; toluene / -65 - 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; samarium diiodide; oxalyl dichloride; potassium hexamethylsilazane; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; L-proline; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; 6: Swern oxidation;
DOI:10.1055/s-2004-822387

Reference yield:

: 17376-04-4
2-phenethyl iodide

: 745058-49-5
{(E)-(R)-1-allyl-4-[(4S,6S)-2,2-dimethyl-6-phenethyl-[1,3]dioxan-4-yl]-but-2-enyloxy}-tert-butyldimethylsilane

Guidance literature:: Multi-step reaction with 11 steps

1.1: t-BuLi / tetrahydrofuran; pentane / 2 h / -78 °C

1.2: 2.217 g / tetrahydrofuran; pentane / -100 - 20 °C

2.1: 96 percent / aq. oxalic acid / diethyl ether / 4 h / 20 °C

3.1: NaBH₄ / methanol / 2 h / 0 °C

4.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

4.2: tetrahydrofuran / 0.5 h

5.1: 2.033 g / tetrahydrofuran / 20 °C

6.1: Bu₃SnH; AIBN / toluene / 1 h / Heating

7.1: 1.035 g / TBAF / tetrahydrofuran / 5 h / 20 °C

8.1: 84 percent / imidazole; PPh₃; I₂ / diethyl ether; acetonitrile / 1 h / 0 °C

9.1: NaH / tetrahydrofuran; dimethylformamide / 0.5 h / 20 °C

9.2: 99 percent / tetrahydrofuran; dimethylformamide

10.1: 87 percent / MCPBA; NaHCO₃ / CH₂Cl₂ / 48 h / 20 °C

11.1: 69 percent / KHMDS / 1,2-dimethoxy-ethane; toluene / -65 - 20 °C

With 1H-imidazole; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; iodine; tert.-butyl lithium; tri-n-butyl-tin hydride; oxalic acid; potassium hexamethylsilazane; sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; pentane; 9.2: Williamson etherification;
DOI:10.1055/s-2004-822387