o-Nitrophenylethylene glycol as photoremovable protective group for aldehydes and ketones: syntheses, scope, and limitations

D Gravel, J Hebert, D Thoraval

Index: Gravel, D.; Herbert, J.; Thoraval, D. Canadian Journal of Chemistry, 1983 , vol. 61, p. 400 - 410

Full Text: HTML

Citation Number: 58

Abstract

The preparation of o-nitrophenylethylene glycol is described along with its application as a photolabile protective group for aldehydes and ketones. Formation of the acetals and ketals is achieved in good to high yields in the usual manner and deprotection is carried out in fair to high yield, by photolysis at 350 nm in an inert solvent such as benzene. Because of the particular nature of the present protective group, its stability to basic and acidic conditions ...

 Related Synthetic Route
2-NITROSTYRENE OXIDE) Structure

39830-70-1

2-NITROSTYRENE ...

~77%

1-(2-Nitrophenyl)-1,2-ethanediol Structure

51673-59-7

1-(2-Nitropheny...

2′-Nitroacetophenone Structure

577-59-3

2′-Nitroacetophenone

~%

1-(2-Nitrophenyl)-1,2-ethanediol Structure

51673-59-7

1-(2-Nitropheny...

2-Bromo-2'-nitroacetophenone Structure

6851-99-6

2-Bromo-2'-nitr...

~%

1-(2-Nitrophenyl)-1,2-ethanediol Structure

51673-59-7

1-(2-Nitropheny...

2-Nitrobenzaldehyde Structure

552-89-6

2-Nitrobenzaldehyde

~%

1-(2-Nitrophenyl)-1,2-ethanediol Structure

51673-59-7

1-(2-Nitropheny...

(3S,8S,10R,13S,14S,17S)-10,13-dimethyl-17-(2-methyl-4-(2-nitrophenyl)-1,3-dioxolan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate Structure

51673-56-4

(3S,8S,10R,13S,...

~81%

3β-acetoxy-pregn-5-en-20-one Structure

1778-02-5

3β-acetoxy-preg...

1-(2-Nitrophenyl)-1,2-ethanediol Structure

51673-59-7

1-(2-Nitropheny...

Acetone Structure

67-64-1

Acetone

~92%

2,2-dimethyl-4-(2-nitrophenyl)-1,3-dioxolane Structure

62635-29-4

2,2-dimethyl-4-...

2-Nitrobenzaldehyde Structure

552-89-6

2-Nitrobenzaldehyde

~%

2,2-dimethyl-4-(2-nitrophenyl)-1,3-dioxolane Structure

62635-29-4

2,2-dimethyl-4-...

2′-Nitroacetophenone Structure

577-59-3

2′-Nitroacetophenone

~%

2,2-dimethyl-4-(2-nitrophenyl)-1,3-dioxolane Structure

62635-29-4

2,2-dimethyl-4-...

2-NITROSTYRENE OXIDE) Structure

39830-70-1

2-NITROSTYRENE ...

~%

2,2-dimethyl-4-(2-nitrophenyl)-1,3-dioxolane Structure

62635-29-4

2,2-dimethyl-4-...

2-Bromo-2'-nitroacetophenone Structure

6851-99-6

2-Bromo-2'-nitr...

~%

2,2-dimethyl-4-(2-nitrophenyl)-1,3-dioxolane Structure

62635-29-4

2,2-dimethyl-4-...

(2R,4R)-4-(2-nitrophenyl)-2-(4-nitrophenyl)-1,3-dioxolane Structure

51673-10-0

(2R,4R)-4-(2-ni...

~83%

4-Nitrobenzaldehyde Structure

555-16-8

4-Nitrobenzaldehyde

2-Bromo-2'-nitroacetophenone Structure

6851-99-6

2-Bromo-2'-nitr...

~85%

2-NITROSTYRENE OXIDE) Structure

39830-70-1

2-NITROSTYRENE ...

2′-Nitroacetophenone Structure

577-59-3

2′-Nitroacetophenone

~%

2-NITROSTYRENE OXIDE) Structure

39830-70-1

2-NITROSTYRENE ...

diazomethane Structure

186581-53-3

diazomethane

2-Nitrobenzaldehyde Structure

552-89-6

2-Nitrobenzaldehyde

~59%

2′-Nitroacetophenone Structure

577-59-3

2′-Nitroacetophenone

2-NITROSTYRENE OXIDE) Structure

39830-70-1

2-NITROSTYRENE ...

(8R,9S,10R,13S,14S,17S)-10,13-dimethyl-4'-(2-nitrophenyl)-1,2,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol Structure

85674-79-9

(8R,9S,10R,13S,...

~31%

Testosterone Structure

58-22-0

Testosterone

5-Androsten-17beta-ol-3-one Structure

571-25-5

5-Androsten-17b...

2-(2-nitrophenyl)-1,4-dioxaspiro[4.5]decane Structure

51673-53-1

2-(2-nitropheny...

~82%

Cyclohexanone Structure

108-94-1

Cyclohexanone


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