1-{3-[3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-5-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-pent-4-enyl]-oxiranyl}-3-(3-{6-[4-(4-methoxy-benzyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-but-3-en-1-ol

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Chemical Name:1-{3-[3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-5-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-pent-4-enyl]-oxiranyl}-3-(3-{6-[4-(4-methoxy-benzyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-but-3-en-1-ol
CAS No.:464914-21-4
Molecular Formula:C₅₂H₇₄O₉Si
Molecular Weight:871.24
Hs Code.:

1-{3-[3-(<i>tert</i>-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-5-(4-methyl-3,6-dihydro-2<i>H</i>-pyran-2-yl)-pent-4-enyl]-oxiranyl}-3-(3-{6-[4-(4-methoxy-benzyloxy)-but-2-ynyl]-3,6-dihydro-2<i>H</i>-pyran-2-yl}-2-methyl-propyl)-but-3-en-1-ol

Synonyms:1-{3-[3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-5-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-pent-4-enyl]-oxiranyl}-3-(3-{6-[4-(4-methoxy-benzyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-but-3-en-1-ol

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Chemical Property of 1-{3-[3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-5-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-pent-4-enyl]-oxiranyl}-3-(3-{6-[4-(4-methoxy-benzyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-but-3-en-1-ol

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Technology Process of 1-{3-[3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-5-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-pent-4-enyl]-oxiranyl}-3-(3-{6-[4-(4-methoxy-benzyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-but-3-en-1-ol

There total 11 articles about 1-{3-[3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-5-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-pent-4-enyl]-oxiranyl}-3-(3-{6-[4-(4-methoxy-benzyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-but-3-en-1-ol 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: 53.0%

: 464914-01-0
((S)-5-{(2R,6R)-6-[4-(4-Methoxy-benzyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-4-methyl-2-methylene-pentyl)-trimethyl-silane

: 464914-10-1
(2R,3S)-3-[(E)-(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-5-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-pent-4-enyl]-oxirane-2-carbaldehyde

: 464914-21-4
1-{3-[3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-5-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-pent-4-enyl]-oxiranyl}-3-(3-{6-[4-(4-methoxy-benzyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-but-3-en-1-ol

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃;
DOI:10.1016/S0040-4039(02)00907-3

Reference yield:

: 79936-62-2
methyl (3R)-3-methyl-5-oxopentanoate

: 464914-21-4
1-{3-[3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-5-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-pent-4-enyl]-oxiranyl}-3-(3-{6-[4-(4-methoxy-benzyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-but-3-en-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: Jacobsen catalyst / various solvent(s) / -25 °C

1.2: TFA / CH₂Cl₂

2.1: 94 percent / CeCl₃*7H₂O; NaBH₄ / methanol / -78 °C

3.1: 91 percent / iPr₂NEt / CH₂Cl₂

4.1: BF₃*OEt₂ / CH₂Cl₂ / -20 °C

4.2: CeCl₃ / tetrahydrofuran / -78 °C

5.1: 53 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

With sodium tetrahydroborate; cerium(III) chloride; boron trifluoride diethyl etherate; N-ethyl-N,N-diisopropylamine; (S,S)-chloro[2,2'-[1,2-cyclohexanediylbis(nitrilomethylidyne)]bis-[4,6-bis(1,1-dimethylethyl)phenolato]]^(2-)-N,N',O,O'-manganese; In methanol; dichloromethane; 1.1: hetero-Diels-Alder cycloaddition / 2.1: Luche reduction;
DOI:10.1016/S0040-4039(02)00907-3

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 464914-21-4
1-{3-[3-(tert-butyl-dimethyl-silanyloxy)-2-(4-methoxy-benzyloxy)-5-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-pent-4-enyl]-oxiranyl}-3-(3-{6-[4-(4-methoxy-benzyloxy)-but-2-ynyl]-3,6-dihydro-2H-pyran-2-yl}-2-methyl-propyl)-but-3-en-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 88 percent / iPrNEt₂ / CH₂Cl₂ / 0 °C

2: 60 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / Heating

3: 75 percent / PPTS / ethanol

4: 94 percent / tBuOOH; (+)-DET; Ti(OiPr)4 / CH₂Cl₂ / -20 °C

5: 88 percent / Dess-Martin periodinane / CH₂Cl₂

6: 53 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; Grubbs catalyst first generation; diethyl (2R,3R)-tartrate; N,N-diethyl-N-isopropylamine; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; Dess-Martin periodane; In ethanol; dichloromethane; 4: Sharpless asymmetric epoxidation / 5: Dess-Martin oxidation;
DOI:10.1016/S0040-4039(02)00907-3