(1S,2R,5R,6S)-5,6-(isopropylidenedioxy)-2-(trimethylsilylethynyl)-3-phenyl-sulfonylcyclohex-3-enol

Base Information

Chemical Name:(1S,2R,5R,6S)-5,6-(isopropylidenedioxy)-2-(trimethylsilylethynyl)-3-phenyl-sulfonylcyclohex-3-enol
CAS No.:205743-78-8
Molecular Formula:C₂₀H₂₆O₅SSi
Molecular Weight:406.575
Hs Code.:

Synonyms:(1S,2R,5R,6S)-5,6-(isopropylidenedioxy)-2-(trimethylsilylethynyl)-3-phenyl-sulfonylcyclohex-3-enol

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Chemical Property of (1S,2R,5R,6S)-5,6-(isopropylidenedioxy)-2-(trimethylsilylethynyl)-3-phenyl-sulfonylcyclohex-3-enol

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Technology Process of (1S,2R,5R,6S)-5,6-(isopropylidenedioxy)-2-(trimethylsilylethynyl)-3-phenyl-sulfonylcyclohex-3-enol

There total 5 articles about (1S,2R,5R,6S)-5,6-(isopropylidenedioxy)-2-(trimethylsilylethynyl)-3-phenyl-sulfonylcyclohex-3-enol 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: 63.0%

: 214278-38-3
5,6-exo-(isopropylidenedioxy)-2-phenylsulfonyl-7-oxabicyclo[2.2.1]hept-2-ene

: 1066-54-2
trimethylsilylacetylene

: 205743-78-8
(1S,2R,5R,6S)-5,6-(isopropylidenedioxy)-2-(trimethylsilylethynyl)-3-phenyl-sulfonylcyclohex-3-enol

Guidance literature:: trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; at 0 ℃; for 0.5h;

5,6-exo-(isopropylidenedioxy)-2-phenylsulfonyl-7-oxabicyclo[2.2.1]hept-2-ene; In tetrahydrofuran; toluene; at 0 ℃; for 0.0833333h;
DOI:10.1016/S0957-4166(99)00358-4

Reference yield: 61.0%

: 54655-07-1
lithium trimethylsilylacetylenide

: 214278-38-3
5,6-exo-(isopropylidenedioxy)-2-phenylsulfonyl-7-oxabicyclo[2.2.1]hept-2-ene

: 205743-78-8
(1S,2R,5R,6S)-5,6-(isopropylidenedioxy)-2-(trimethylsilylethynyl)-3-phenyl-sulfonylcyclohex-3-enol

Guidance literature:: In toluene; at 0 ℃;
DOI:10.1016/S0040-4039(98)00109-9

Reference yield:

: (1R,4S)-4,7,7-Trimethyl-3-oxo-2-oxa-bicyclo[2.2.1]heptane-1-carboxylic acid (1R,2R,3R,4S,5S,6R)-3-benzenesulfonyl-5,6-bis-benzyloxy-7-oxa-bicyclo[2.2.1]hept-2-yl ester

: 205743-78-8
(1S,2R,5R,6S)-5,6-(isopropylidenedioxy)-2-(trimethylsilylethynyl)-3-phenyl-sulfonylcyclohex-3-enol

Guidance literature:: Multi-step reaction with 4 steps

1.1: EtSH; BF₃*Et₂O / 0.25 h

2.1: 81 percent / p-TsOH / acetone / 0.5 h

3.1: 71 percent / aq. K₂CO₃ / tetrahydrofuran / 48 h / 20 °C

4.1: n-BuLi / tetrahydrofuran / 0.5 h / 0 °C

4.2: 63 percent / toluene; tetrahydrofuran / 0.08 h / 0 °C

With n-butyllithium; boron trifluoride diethyl etherate; potassium carbonate; toluene-4-sulfonic acid; ethanethiol; In tetrahydrofuran; acetone; 1.1: debenzylation / 2.1: cyclocondensation / 3.1: Elimination / 4.1: Metallation / 4.2: Ring cleavage;
DOI:10.1016/S0957-4166(99)00358-4