(2R,3S,4S,5S)-2,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclooctanone

Base Information

Chemical Name:(2R,3S,4S,5S)-2,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclooctanone
CAS No.:330589-52-1
Molecular Formula:C₃₅H₄₆O₅Si
Molecular Weight:574.833
Hs Code.:

Synonyms:(2R,3S,4S,5S)-2,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclooctanone

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Chemical Property of (2R,3S,4S,5S)-2,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclooctanone

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Technology Process of (2R,3S,4S,5S)-2,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclooctanone

There total 3 articles about (2R,3S,4S,5S)-2,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclooctanone 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: 93.0%

: tert-Butyl-dimethyl-((E)-(1S,6R,7S,8S)-6,7,8-tris-benzyloxy-5-methoxy-cyclooct-4-enyloxy)-silane

: 330589-52-1
(2R,3S,4S,5S)-2,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclooctanone

Guidance literature:: With toluene-4-sulfonic acid; In tetrahydrofuran; water; for 0.5h;
DOI:10.1021/ol007047+

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 330589-52-1
(2R,3S,4S,5S)-2,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclooctanone

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 0.5 h / -20 °C

2: 93 percent / p-TsOH / tetrahydrofuran; H₂O / 0.5 h

With toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol007047+

Reference yield:

: (E)-(1S,6R,7S,8R)-6,7,8-Tris-benzyloxy-5-methoxy-cyclooct-4-enol

: 330589-52-1
(2R,3S,4S,5S)-2,3,4-Tris-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclooctanone

Guidance literature:: Multi-step reaction with 2 steps

1: 95 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 0.5 h / -20 °C

2: 93 percent / p-TsOH / tetrahydrofuran; H₂O / 0.5 h

With toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol007047+