2-((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-(t-butyldimethylsiloxy)octahydropyrano[3,2-b]pyran-2-yl)acetoaldehyde

Base Information

Chemical Name:2-((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-(t-butyldimethylsiloxy)octahydropyrano[3,2-b]pyran-2-yl)acetoaldehyde
CAS No.:1338566-14-5
Molecular Formula:C₃₁H₄₄O₆Si
Molecular Weight:540.772
Hs Code.:

Synonyms:2-((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-(t-butyldimethylsiloxy)octahydropyrano[3,2-b]pyran-2-yl)acetoaldehyde

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Chemical Property of 2-((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-(t-butyldimethylsiloxy)octahydropyrano[3,2-b]pyran-2-yl)acetoaldehyde

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Technology Process of 2-((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-(t-butyldimethylsiloxy)octahydropyrano[3,2-b]pyran-2-yl)acetoaldehyde

There total 6 articles about 2-((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-(t-butyldimethylsiloxy)octahydropyrano[3,2-b]pyran-2-yl)acetoaldehyde 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: 97.0%

: 1338566-13-4
ethyl ((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-(t-butyldimethylsiloxy)octahydropyrano[3,2-b]pyran-2-yl)acetate

: 1338566-14-5
2-((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-(t-butyldimethylsiloxy)octahydropyrano[3,2-b]pyran-2-yl)acetoaldehyde

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; Inert atmosphere;
DOI:10.1021/jo302267f

Reference yield:

: 436153-70-7
[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-methanol

: 1338566-14-5
2-((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-(t-butyldimethylsiloxy)octahydropyrano[3,2-b]pyran-2-yl)acetoaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1: n-butyllithium / tetrahydrofuran / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / Inert atmosphere

3: 4-methyl-morpholine / dichloromethane / Inert atmosphere

4: sodium hydrogencarbonate; methyl iodide; water / [D₃]acetonitrile / Inert atmosphere

5: samarium diiodide / tetrahydrofuran; methanol / 0 °C / Inert atmosphere

6: 2,6-dimethylpyridine / dichloromethane / 0 °C / Inert atmosphere

7: diisobutylaluminium hydride / dichloromethane / -78 °C / Inert atmosphere

With 4-methyl-morpholine; 2,6-dimethylpyridine; n-butyllithium; samarium diiodide; tetrabutyl ammonium fluoride; water; diisobutylaluminium hydride; sodium hydrogencarbonate; methyl iodide; In tetrahydrofuran; methanol; dichloromethane; [D₃]acetonitrile;
DOI:10.1021/jo302267f

Reference yield:

: 1338566-08-7
(2S,3R,5S,6R)-5-(benzyloxy)-6-((benzyloxy)methyl)-2-((1,3-dithian-2-yl)methyl)tetrahydro-2H-pyran-3-ol

: 1338566-14-5
2-((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-(t-butyldimethylsiloxy)octahydropyrano[3,2-b]pyran-2-yl)acetoaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1: 4-methyl-morpholine / dichloromethane / Inert atmosphere

2: sodium hydrogencarbonate; methyl iodide; water / [D₃]acetonitrile / Inert atmosphere

3: samarium diiodide / tetrahydrofuran; methanol / 0 °C / Inert atmosphere

4: 2,6-dimethylpyridine / dichloromethane / 0 °C / Inert atmosphere

5: diisobutylaluminium hydride / dichloromethane / -78 °C / Inert atmosphere

With 4-methyl-morpholine; 2,6-dimethylpyridine; samarium diiodide; water; diisobutylaluminium hydride; sodium hydrogencarbonate; methyl iodide; In tetrahydrofuran; methanol; dichloromethane; [D₃]acetonitrile;
DOI:10.1021/jo302267f