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

Base Information

Chemical Name:(2S,3R,4S,5S,6R)-2-(tert-butyldimethylsilyloxy)-4,6-((R)-benzylidenedioxy)-3,5-dimethylheptanal
CAS No.:251099-45-3
Molecular Formula:C₂₂H₃₆O₄Si
Molecular Weight:392.611
Hs Code.:

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

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

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

There total 12 articles about (2S,3R,4S,5S,6R)-2-(tert-butyldimethylsilyloxy)-4,6-((R)-benzylidenedioxy)-3,5-dimethylheptanal 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: 95.0%

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

: 251099-45-3
(2S,3R,4S,5S,6R)-2-(tert-butyldimethylsilyloxy)-4,6-((R)-benzylidenedioxy)-3,5-dimethylheptanal

Guidance literature:: With pyridine; Dess-Martin periodane; In dichloromethane; at 0 - 20 ℃; for 2.66667h;
DOI:10.1021/ja020853m

Reference yield:

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

: 251099-45-3
(2S,3R,4S,5S,6R)-2-(tert-butyldimethylsilyloxy)-4,6-((R)-benzylidenedioxy)-3,5-dimethylheptanal

Guidance literature:: Multi-step reaction with 6 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

With pyridine; camphor-10-sulfonic acid; titanium tetrachloride; Dess-Martin periodane; 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

: 251099-45-3
(2S,3R,4S,5S,6R)-2-(tert-butyldimethylsilyloxy)-4,6-((R)-benzylidenedioxy)-3,5-dimethylheptanal

Guidance literature:: Multi-step reaction with 3 steps

1: 89 percent / CSA / 12 h / 20 °C

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

3: 95 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2.67 h / 0 - 20 °C

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