(3S,4R,5S,6S,7R)-3-(tert-butyldimethylsilyloxy)-5,7-((R)-benzylidenedioxy)-4,6-dimethyl-1-octene-2-yl-trifluoromethanesulfonate

Base Information

Chemical Name:(3S,4R,5S,6S,7R)-3-(tert-butyldimethylsilyloxy)-5,7-((R)-benzylidenedioxy)-4,6-dimethyl-1-octene-2-yl-trifluoromethanesulfonate
CAS No.:251099-49-7
Molecular Formula:C₂₄H₃₇F₃O₆SSi
Molecular Weight:538.701
Hs Code.:

Synonyms:(3S,4R,5S,6S,7R)-3-(tert-butyldimethylsilyloxy)-5,7-((R)-benzylidenedioxy)-4,6-dimethyl-1-octene-2-yl-trifluoromethanesulfonate

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Chemical Property of (3S,4R,5S,6S,7R)-3-(tert-butyldimethylsilyloxy)-5,7-((R)-benzylidenedioxy)-4,6-dimethyl-1-octene-2-yl-trifluoromethanesulfonate

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Technology Process of (3S,4R,5S,6S,7R)-3-(tert-butyldimethylsilyloxy)-5,7-((R)-benzylidenedioxy)-4,6-dimethyl-1-octene-2-yl-trifluoromethanesulfonate

There total 15 articles about (3S,4R,5S,6S,7R)-3-(tert-butyldimethylsilyloxy)-5,7-((R)-benzylidenedioxy)-4,6-dimethyl-1-octene-2-yl-trifluoromethanesulfonate 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: 88.0%

: 37595-74-7
N,N-phenylbistrifluoromethane-sulfonimide

: 251099-47-5
(3S,4R,5S,6S,7R)-3-(tert-butyldimethylsilyloxy)-5,7-((R)-benzylidenedioxy)-4,6-dimethyloctan-2-one

: 251099-49-7
(3S,4R,5S,6S,7R)-3-(tert-butyldimethylsilyloxy)-5,7-((R)-benzylidenedioxy)-4,6-dimethyl-1-octene-2-yl-trifluoromethanesulfonate

Guidance literature:: (3S,4R,5S,6S,7R)-3-(tert-butyldimethylsilyloxy)-5,7-((R)-benzylidenedioxy)-4,6-dimethyloctan-2-one; With potassium hexamethylsilazane; at -78 ℃;

N,N-phenylbistrifluoromethane-sulfonimide; at -78 ℃;
DOI:10.1021/ja992370x

Reference yield:

: 184528-64-1
(2S,3S)-3,4-(di(tert-butyldimethylsilyloxy))-2-methyl-butanal

: 251099-49-7
(3S,4R,5S,6S,7R)-3-(tert-butyldimethylsilyloxy)-5,7-((R)-benzylidenedioxy)-4,6-dimethyl-1-octene-2-yl-trifluoromethanesulfonate

Guidance literature:: Multi-step reaction with 9 steps

1.1: TiCl₄ / CH₂Cl₂ / 49 h / -78 - -30 °C

2.1: O₃; pyridine / methanol / -78 °C

2.2: Me₂S / methanol / 6 h / 20 °C

3.1: 89 percent / tetramethylammonium triacetoxyborohydride / acetonitrile; acetic acid / 26 h / -20 - 0 °C

4.1: 89 percent / CSA / 12 h / 20 °C

5.1: 96 percent / HF*py; pyridine / tetrahydrofuran / 3.67 h / 0 - 20 °C

6.1: 95 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2.67 h / 0 - 20 °C

7.1: CH₂Cl₂; diethyl ether / 0.25 h / -78 °C

8.1: 516 mg / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 4.5 h / 0 - 20 °C

9.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C

9.2: 88 percent / tetrahydrofuran; toluene / 1 h / -78 °C

With pyridine; camphor-10-sulfonic acid; titanium tetrachloride; potassium hexamethylsilazane; Dess-Martin periodane; pyridine hydrogenfluoride; ozone; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetic acid; toluene; acetonitrile;
DOI:10.1021/ja020853m

Reference yield:

: 251099-43-1
(2S,3R,4S,5S,6R)-2-(tert-butyldimethylsilyloxy)-4,6-((R)-benzylidenedioxy)-3,5-dimethylheptanol

: 251099-49-7
(3S,4R,5S,6S,7R)-3-(tert-butyldimethylsilyloxy)-5,7-((R)-benzylidenedioxy)-4,6-dimethyl-1-octene-2-yl-trifluoromethanesulfonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 95 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2.67 h / 0 - 20 °C

2.1: CH₂Cl₂; diethyl ether / 0.25 h / -78 °C

3.1: 516 mg / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 4.5 h / 0 - 20 °C

4.1: potassium bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C

4.2: 88 percent / tetrahydrofuran; toluene / 1 h / -78 °C

With pyridine; potassium hexamethylsilazane; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1021/ja020853m