(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

Base Information

Chemical Name:(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
CAS No.:464914-10-1
Molecular Formula:C₂₈H₄₂O₆Si
Molecular Weight:502.723
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 6 articles about (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 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: 88.0%

: 464914-20-3
{(2S,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]-oxiranyl}-methanol

: 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

Guidance literature:: With Dess-Martin periodane; In dichloromethane;
DOI:10.1016/S0040-4039(02)00907-3

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 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

Guidance literature:: Multi-step reaction with 5 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

With titanium(IV) isopropylate; tert.-butylhydroperoxide; Grubbs catalyst first generation; diethyl (2R,3R)-tartrate; N,N-diethyl-N-isopropylamine; 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

Reference yield:

: 464914-19-0
(2E,7E)(5S,6S)-6-(tert-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-8-((2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-octa-2,7-dien-1-ol

: 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

Guidance literature:: Multi-step reaction with 2 steps

1: 94 percent / tBuOOH; (+)-DET; Ti(OiPr)4 / CH₂Cl₂ / -20 °C

2: 88 percent / Dess-Martin periodinane / CH₂Cl₂

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; Dess-Martin periodane; In dichloromethane; 1: Sharpless asymmetric epoxidation / 2: Dess-Martin oxidation;
DOI:10.1016/S0040-4039(02)00907-3