(2S,5S,6S)-5-((E)-2-Benzenesulfonyl-vinyl)-6-[(R)-3-bromo-2-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-2-tert-butyl-5-methyl-[1,3]dioxan-4-one

Base Information

Chemical Name:(2S,5S,6S)-5-((E)-2-Benzenesulfonyl-vinyl)-6-[(R)-3-bromo-2-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-2-tert-butyl-5-methyl-[1,3]dioxan-4-one
CAS No.:190730-66-6
Molecular Formula:C₂₇H₄₁BrO₆SSi
Molecular Weight:601.674
Hs Code.:

(2S,5S,6S)-5-((E)-2-Benzenesulfonyl-vinyl)-6-[(R)-3-bromo-2-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-2-tert-butyl-5-methyl-[1,3]dioxan-4-one

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Chemical Property of (2S,5S,6S)-5-((E)-2-Benzenesulfonyl-vinyl)-6-[(R)-3-bromo-2-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-2-tert-butyl-5-methyl-[1,3]dioxan-4-one

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Technology Process of (2S,5S,6S)-5-((E)-2-Benzenesulfonyl-vinyl)-6-[(R)-3-bromo-2-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-2-tert-butyl-5-methyl-[1,3]dioxan-4-one

There total 9 articles about (2S,5S,6S)-5-((E)-2-Benzenesulfonyl-vinyl)-6-[(R)-3-bromo-2-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-2-tert-butyl-5-methyl-[1,3]dioxan-4-one 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:

: 630-19-3
pivalaldehyde

: 190730-66-6
(2S,5S,6S)-5-((E)-2-Benzenesulfonyl-vinyl)-6-[(R)-3-bromo-2-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-2-tert-butyl-5-methyl-[1,3]dioxan-4-one

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / i-PrOSiMe₃, TMSOTf / CH₂Cl₂ / 1.) -78 deg C, 0.5 h, 2.) -15 deg C, 8 h

2: 1.) hexamethyldisilazane, BuLi / 1.) THF, pentane, -78 deg C, 40 min, 2.) THF, -78 deg C, 9 h; -78 deg C to room temperature, 1 h

With n-butyllithium; isopropoxytrimethylsilane; trimethylsilyl trifluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane;
DOI:10.1016/S0040-4020(97)00412-2

Reference yield:

: 190730-59-7
(R)-4-Bromo-3-(tert-butyl-dimethyl-silanyloxy)-pent-4-en-1-ol

: 190730-66-6
(2S,5S,6S)-5-((E)-2-Benzenesulfonyl-vinyl)-6-[(R)-3-bromo-2-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-2-tert-butyl-5-methyl-[1,3]dioxan-4-one

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / Dess-Martin periodinane / CH₂Cl₂ / 2.5 h / Ambient temperature

2: 1.) i-Pr₂NEt, Bu₂BOTf, 3.) aq. H₂O₂

3: 71 percent / LiOH*H₂O, aq. H₂O₂ / tetrahydrofuran / 5 h / Ambient temperature

4: 90 percent / i-PrOSiMe₃, TMSOTf / CH₂Cl₂ / 1.) -78 deg C, 0.5 h, 2.) -15 deg C, 8 h

5: 1.) hexamethyldisilazane, BuLi / 1.) THF, pentane, -78 deg C, 40 min, 2.) THF, -78 deg C, 9 h; -78 deg C to room temperature, 1 h

With lithium hydroxide; n-butyllithium; isopropoxytrimethylsilane; trimethylsilyl trifluoromethanesulfonate; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(97)00412-2

Reference yield:

: 190847-56-4
(R)-4-Bromo-3-(tert-butyl-dimethyl-silanyloxy)-pent-4-enal

: 190730-66-6
(2S,5S,6S)-5-((E)-2-Benzenesulfonyl-vinyl)-6-[(R)-3-bromo-2-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-2-tert-butyl-5-methyl-[1,3]dioxan-4-one

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) i-Pr₂NEt, Bu₂BOTf, 3.) aq. H₂O₂

2: 71 percent / LiOH*H₂O, aq. H₂O₂ / tetrahydrofuran / 5 h / Ambient temperature

3: 90 percent / i-PrOSiMe₃, TMSOTf / CH₂Cl₂ / 1.) -78 deg C, 0.5 h, 2.) -15 deg C, 8 h

4: 1.) hexamethyldisilazane, BuLi / 1.) THF, pentane, -78 deg C, 40 min, 2.) THF, -78 deg C, 9 h; -78 deg C to room temperature, 1 h

With lithium hydroxide; n-butyllithium; isopropoxytrimethylsilane; trimethylsilyl trifluoromethanesulfonate; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; N-ethyl-N,N-diisopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane;
DOI:10.1016/S0040-4020(97)00412-2