(2S,3S,4S,5S)-1,2-O-dibenzyl-4,5-epoxy-5-(trimethylsilyl)pentane-1,2,3-triol

Base Information

Chemical Name:(2S,3S,4S,5S)-1,2-O-dibenzyl-4,5-epoxy-5-(trimethylsilyl)pentane-1,2,3-triol
CAS No.:176909-83-4
Molecular Formula:C₂₂H₃₀O₄Si
Molecular Weight:386.563
Hs Code.:

Synonyms:(2S,3S,4S,5S)-1,2-O-dibenzyl-4,5-epoxy-5-(trimethylsilyl)pentane-1,2,3-triol

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Chemical Property of (2S,3S,4S,5S)-1,2-O-dibenzyl-4,5-epoxy-5-(trimethylsilyl)pentane-1,2,3-triol

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Technology Process of (2S,3S,4S,5S)-1,2-O-dibenzyl-4,5-epoxy-5-(trimethylsilyl)pentane-1,2,3-triol

There total 5 articles about (2S,3S,4S,5S)-1,2-O-dibenzyl-4,5-epoxy-5-(trimethylsilyl)pentane-1,2,3-triol 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:

: 176909-82-3
(E)-(3R,4S)-4,5-Bis-benzyloxy-1-trimethylsilanyl-pent-1-en-3-ol

: 176909-83-4
(2S,3S,4S,5S)-1,2-O-dibenzyl-4,5-epoxy-5-(trimethylsilyl)pentane-1,2,3-triol

Guidance literature:: With titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; 4 A molecular sieve; In dichloromethane; toluene; at -22 - -20 ℃; for 19h;
DOI:10.1016/0957-4166(96)00072-9

Reference yield:

: 119046-51-4
(2S,3S,4S)-1-O-benzyl-3,4-epoxy-4-(trimethylsilyl)butane-1,2-diol

: 176909-83-4
(2S,3S,4S,5S)-1,2-O-dibenzyl-4,5-epoxy-5-(trimethylsilyl)pentane-1,2,3-triol

Guidance literature:: Multi-step reaction with 3 steps

1: 99 percent / tetrabutylammonium bromide, 50percent aq. NaOH / benzene / 16 h / Ambient temperature

2: 1.) BuLi, 3.) methanolic HClO₄, 4.) thiophenol, AIBN

3: molecular sieves 4 Angstroem, L-(+)-DIPT, Ti(Oi-Pr)4, TBHP / CH₂Cl₂; toluene / 19 h / -22 - -20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; n-butyllithium; perchloric acid; 2,2'-azobis(isobutyronitrile); L-(+)-diisopropyl tartrate; 4 A molecular sieve; tetrabutylammomium bromide; thiophenol; In dichloromethane; toluene; benzene;
DOI:10.1016/0957-4166(96)00072-9

Reference yield:

: 138722-29-9
(2S,3S)-1-O-benzyl-2,3-epoxy-3-(trimethylsilyl)propane-1-ol

: 176909-83-4
(2S,3S,4S,5S)-1,2-O-dibenzyl-4,5-epoxy-5-(trimethylsilyl)pentane-1,2,3-triol

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) BuLi, 3.) thiophenol, AIBN

2: 85 percent / molecular sieves 4 Angstroem, L-(+)-DIPT, Ti(Oi-Pr)4, TBHP / CH₂Cl₂; toluene / 21 h / -22 - -20 °C

3: 99 percent / tetrabutylammonium bromide, 50percent aq. NaOH / benzene / 16 h / Ambient temperature

4: 1.) BuLi, 3.) methanolic HClO₄, 4.) thiophenol, AIBN

5: molecular sieves 4 Angstroem, L-(+)-DIPT, Ti(Oi-Pr)4, TBHP / CH₂Cl₂; toluene / 19 h / -22 - -20 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; n-butyllithium; perchloric acid; 2,2'-azobis(isobutyronitrile); L-(+)-diisopropyl tartrate; 4 A molecular sieve; tetrabutylammomium bromide; thiophenol; In dichloromethane; toluene; benzene;
DOI:10.1016/0957-4166(96)00072-9