4-((E)-2-{(2R,3S,4S,5S,6R)-6-[2-(4-Methoxy-benzyloxy)-ethyl]-3,5-dimethyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl}-propenyl)-2-methyl-oxazole

Base Information

Chemical Name:4-((E)-2-{(2R,3S,4S,5S,6R)-6-[2-(4-Methoxy-benzyloxy)-ethyl]-3,5-dimethyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl}-propenyl)-2-methyl-oxazole
CAS No.:224578-30-7
Molecular Formula:C₃₀H₄₇NO₅Si
Molecular Weight:529.792
Hs Code.:

Synonyms:4-((E)-2-{(2R,3S,4S,5S,6R)-6-[2-(4-Methoxy-benzyloxy)-ethyl]-3,5-dimethyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl}-propenyl)-2-methyl-oxazole

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Chemical Property of 4-((E)-2-{(2R,3S,4S,5S,6R)-6-[2-(4-Methoxy-benzyloxy)-ethyl]-3,5-dimethyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl}-propenyl)-2-methyl-oxazole

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Technology Process of 4-((E)-2-{(2R,3S,4S,5S,6R)-6-[2-(4-Methoxy-benzyloxy)-ethyl]-3,5-dimethyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl}-propenyl)-2-methyl-oxazole

There total 14 articles about 4-((E)-2-{(2R,3S,4S,5S,6R)-6-[2-(4-Methoxy-benzyloxy)-ethyl]-3,5-dimethyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl}-propenyl)-2-methyl-oxazole 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: 40.0%

: (E)-(3S,4S,5R,6S,7R)-9-(4-Methoxy-benzyloxy)-7-methoxymethoxy-2,4,6-trimethyl-1-(2-methyl-oxazol-4-yl)-5-triethylsilanyloxy-non-1-en-3-ol

: 224578-30-7
4-((E)-2-{(2R,3S,4S,5S,6R)-6-[2-(4-Methoxy-benzyloxy)-ethyl]-3,5-dimethyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl}-propenyl)-2-methyl-oxazole

Guidance literature:: With pyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at -20 ℃; for 16h;
DOI:10.1016/S0040-4039(99)00209-9

Reference yield:

: 224578-29-4
(E)-(3R,4S,5R,6S,7R)-9-(4-Methoxy-benzyloxy)-7-methoxymethoxy-2,4,6-trimethyl-1-(2-methyl-oxazol-4-yl)-5-triethylsilanyloxy-non-1-en-3-ol

: 224578-30-7
4-((E)-2-{(2R,3S,4S,5S,6R)-6-[2-(4-Methoxy-benzyloxy)-ethyl]-3,5-dimethyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl}-propenyl)-2-methyl-oxazole

Guidance literature:: With trifluoromethylsulfonic anhydride; In pyridine; at -20 ℃;
DOI:10.1002/anie.200390322

Reference yield:

: 128461-65-4
3-(p-methoxybenzyloxy)propanal

: 224578-30-7
4-((E)-2-{(2R,3S,4S,5S,6R)-6-[2-(4-Methoxy-benzyloxy)-ethyl]-3,5-dimethyl-4-triethylsilanyloxy-tetrahydro-pyran-2-yl}-propenyl)-2-methyl-oxazole

Guidance literature:: Multi-step reaction with 11 steps

1: 96 percent / Bu₂BOTf, Et₃N / CH₂Cl₂ / -78 °C

2: 84 percent / i-Pr₂NEt

3: 89 percent / LiBH₄ / diethyl ether; H₂O

4: Swern

5: Bu₂BOTf, Et₃N / CH₂Cl₂ / -40 °C

6: 84 percent / imidazole / CH₂Cl₂

7: 89 percent / tetrahydrofuran

8: 88 percent / n-BuLi / tetrahydrofuran / -78 °C

9: NaH / tetrahydrofuran

10: NaBH₄, CeCl₃*7H₂O / methanol / 0 °C

11: 40 percent / Tf₂O, pyridine / CH₂Cl₂ / 16 h / -20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; lithium borohydride; n-butyllithium; cerium(III) chloride; trifluoromethylsulfonic anhydride; di-n-butylboryl trifluoromethanesulfonate; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;
DOI:10.1016/S0040-4039(99)00209-9