(2S,3R,4S,5S,6R)-2-(tert-butyldimethylsilyloxy)-4,6-((R)-benzylidenedioxy)-3,5-dimethylheptanol

Base Information

Chemical Name:(2S,3R,4S,5S,6R)-2-(tert-butyldimethylsilyloxy)-4,6-((R)-benzylidenedioxy)-3,5-dimethylheptanol
CAS No.:251099-43-1
Molecular Formula:C₂₂H₃₈O₄Si
Molecular Weight:394.627
Hs Code.:

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

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

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

There total 11 articles about (2S,3R,4S,5S,6R)-2-(tert-butyldimethylsilyloxy)-4,6-((R)-benzylidenedioxy)-3,5-dimethylheptanol 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: 96.0%

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

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

Guidance literature:: With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 0 - 20 ℃; for 3.66667h;
DOI:10.1021/ja020853m

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

: 251099-39-5
(2R,3S,4S,5R,6S)-6,7-(di(tert-butyldimethylsilyloxy))-3,5-dimethylheptane-2,4-diol

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

Guidance literature:: Multi-step reaction with 2 steps

1: 89 percent / CSA / 12 h / 20 °C

2: 96 percent / HF*py; pyridine / tetrahydrofuran / 3.67 h / 0 - 20 °C

With pyridine; camphor-10-sulfonic acid; pyridine hydrogenfluoride; In tetrahydrofuran;
DOI:10.1021/ja020853m