(-)-((2R,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether

Base Information

Chemical Name:(-)-((2R,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether
CAS No.:685142-69-2
Molecular Formula:C₃₂H₄₀O₅Si
Molecular Weight:532.752
Hs Code.:

Synonyms:(-)-((2R,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether

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Chemical Property of (-)-((2R,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether

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Technology Process of (-)-((2R,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether

There total 9 articles about (-)-((2R,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether 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: 82.0%

: 1033126-30-5
C₂₄H₃₂O₄Si

: 2746-25-0
p-Methoxybenzyl bromide

: 685142-69-2
(-)-((2R,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 4h;
DOI:10.1021/jo8004233

Reference yield:

: 1779-49-3
Methyltriphenylphosphonium bromide

: 685142-68-1
(2S,4R,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-carbaldehyde

: 685142-69-2
(-)-((2R,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at 20 ℃; for 3h;
DOI:10.1016/j.tet.2003.07.012

Reference yield:

: 35781-73-8
(-)-(3aR,5R,6aR)-methyl 3a,5,6,6a-tetrahydro-2,2-dimethylfuro[2,3-d][1,3]dioxole-5-carboxylate

: 685142-69-2
(-)-((2R,4R,5R)-4-(4-methoxybenzyloxy)-5-methoxy-2-vinyltetrahydrofuran-2-yl)methyl tert-butyldiphenylsilyl ether

Guidance literature:: Multi-step reaction with 6 steps

1.1: HCl / 1 h / Heating

1.2: 3.88 g / comphorsulfonic acid / CH₂Cl₂ / 72 h / 0 - 20 °C

2.1: 59 percent / nBuLi; iPr₂NH / hexane; tetrahydrofuran / -78 - -10 °C

3.1: 94 percent / imidazole / dimethylformamide / 3 h / 20 °C

4.1: Dibal-H / CH₂Cl₂; hexane / 1 h / -20 °C

5.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

6.1: 847 mg / nBuLi / tetrahydrofuran; hexane / 3 h / 20 °C

With 1H-imidazole; hydrogenchloride; n-butyllithium; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 5.1: Swern oxidation / 6.1: Wittig olefination;
DOI:10.1016/j.tet.2003.07.012