(1S,2R,3S,4R)-1-O-benzyl-2-O-tert-butyldimethylsilyl-4-vinyl-cyclopentane-1,2,3-triol

Base Information

Chemical Name:(1S,2R,3S,4R)-1-O-benzyl-2-O-tert-butyldimethylsilyl-4-vinyl-cyclopentane-1,2,3-triol
CAS No.:1410003-48-3
Molecular Formula:C₂₀H₃₂O₃Si
Molecular Weight:348.558
Hs Code.:

Synonyms:(1S,2R,3S,4R)-1-O-benzyl-2-O-tert-butyldimethylsilyl-4-vinyl-cyclopentane-1,2,3-triol

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Chemical Property of (1S,2R,3S,4R)-1-O-benzyl-2-O-tert-butyldimethylsilyl-4-vinyl-cyclopentane-1,2,3-triol

Chemical Property:

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Technology Process of (1S,2R,3S,4R)-1-O-benzyl-2-O-tert-butyldimethylsilyl-4-vinyl-cyclopentane-1,2,3-triol

There total 10 articles about (1S,2R,3S,4R)-1-O-benzyl-2-O-tert-butyldimethylsilyl-4-vinyl-cyclopentane-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:

: (2R,3S)-2-O-tert-butyl-dimethylsilyl-3-O-benzyl-7-bromo-2,3-dihydroxy-hept-5E-enal

: (1S,2R,3R)-1-O-benzyl-2-O-tert-butyldimethylsilyl-4-vinyl-cyclopentane-1,2,3-triol

: 1410003-48-3
(1S,2R,3S,4R)-1-O-benzyl-2-O-tert-butyldimethylsilyl-4-vinyl-cyclopentane-1,2,3-triol

: 1410003-52-9
(1S,2R,3S,4S)-1-O-benzyl-2-O-tert-butyldimethylsilyl-4-vinyl-cyclopentane-1,2,3-triol

Guidance literature:: With tin(II) chloride dihdyrate; zinc; In tetrahydrofuran; at 15 - 20 ℃; for 18h;
DOI:10.1016/j.tetasy.2012.09.007

Reference yield:

: 1239889-27-0
(4S,5R)-4-O-benzyl-5,6-di-O-tert-butyldimethylsilyl-4,5,6-trihydroxy-hex-1-ene

: 1410003-48-3
(1S,2R,3S,4R)-1-O-benzyl-2-O-tert-butyldimethylsilyl-4-vinyl-cyclopentane-1,2,3-triol

Guidance literature:: Multi-step reaction with 8 steps

1.1: ozone / dichloromethane / -78 °C

1.2: -78 - 20 °C

2.1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.2: 4.75 h / 0 - 20 °C

3.1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1.5 h / -78 °C

4.1: triethylamine / dichloromethane / 3 h / 0 - 20 °C

5.1: sodium hydrogencarbonate; sodium bromide / acetone / 25 °C

6.1: hydrogenchloride; water / chloroform / 36 h / 20 °C

7.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C

8.1: ammonium chloride; zinc / tetrahydrofuran; water / Saturated solution

With hydrogenchloride; water; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; ammonium chloride; Dess-Martin periodane; ozone; triethylamine; sodium bromide; zinc; In tetrahydrofuran; hexane; dichloromethane; chloroform; water; acetone;
DOI:10.1016/j.tetasy.2012.09.007

Reference yield:

: 1410003-39-2
(5S,6R)-5-O-benzyl-6-O-tert-butyl-dimethylsilyl-1-bromo-5,6,7-trihydroxy-hept-2E-ene

: 1410003-48-3
(1S,2R,3S,4R)-1-O-benzyl-2-O-tert-butyldimethylsilyl-4-vinyl-cyclopentane-1,2,3-triol

Guidance literature:: Multi-step reaction with 2 steps

1: Dess-Martin periodane / dichloromethane / 0 - 20 °C

2: ammonium chloride; zinc / tetrahydrofuran; water / Saturated solution

With ammonium chloride; Dess-Martin periodane; zinc; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.tetasy.2012.09.007