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

Base Information

Chemical Name:(3S,4R,5S,6S,7R)-3-(tert-butyldimethylsilyloxy)-5,7-((R)-benzylidenedioxy)-4,6-dimethyloctan-2-one
CAS No.:251099-47-5
Molecular Formula:C₂₃H₃₈O₄Si
Molecular Weight:406.638
Hs Code.:

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

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Chemical Property of (3S,4R,5S,6S,7R)-3-(tert-butyldimethylsilyloxy)-5,7-((R)-benzylidenedioxy)-4,6-dimethyloctan-2-one

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Technology Process of (3S,4R,5S,6S,7R)-3-(tert-butyldimethylsilyloxy)-5,7-((R)-benzylidenedioxy)-4,6-dimethyloctan-2-one

There total 14 articles about (3S,4R,5S,6S,7R)-3-(tert-butyldimethylsilyloxy)-5,7-((R)-benzylidenedioxy)-4,6-dimethyloctan-2-one 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: 98.0%

: (3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-((2R,4S,5S,6R)-5,6-dimethyl-2-phenyl-[1,3]dioxan-4-yl)-pentan-2-ol

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

Guidance literature:: With Dess-Martin periodane;
DOI:10.1021/ja992370x

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 8 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

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

Reference yield:

: 251099-41-9
(2S,3R,4S,5S,6R)-1,2-(di(tert-butyldimethylsilyloxy))-4,6-((R)-benzylidenedioxy)-3,5-dimethylheptane

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

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / HF*py; pyridine / tetrahydrofuran / 3.67 h / 0 - 20 °C

2: 95 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2.67 h / 0 - 20 °C

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

4: 516 mg / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 4.5 h / 0 - 20 °C

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