Regioselectivity among six secondary hydroxyl groups: selective acylation of the least reactive hydroxyl groups of inositol

2012 ◽  
Vol 48 (18) ◽  
pp. 2448 ◽  
Author(s):  
Amol M. Vibhute ◽  
Adiyala Vidyasagar ◽  
Saritha Sarala ◽  
Kana M. Sureshan
Keyword(s):  
Hydroxyl Groups ◽  
Secondary Hydroxyl ◽  
Selective Acylation

ChemInform Abstract: Regioselectivity Among Six Secondary Hydroxyl Groups: Selective Acylation of the Least Reactive Hydroxyl Groups of Inositol

ChemInform ◽  
2012 ◽  
Vol 43 (27) ◽  
pp. no-no
Author(s):  
Amol M. Vibhute ◽  
Adiyala Vidyasagar ◽  
Saritha Sarala ◽  
Kana M. Sureshan
Keyword(s):  
Hydroxyl Groups ◽  
Secondary Hydroxyl ◽  
Selective Acylation

Selective transacylation reactions on 4-aryl-3,4-dihydropyrimidin-2-ones and nucleosides mediated by novel lipases

2005 ◽  
Vol 77 (1) ◽  
pp. 237-243 ◽  
Author(s):  
◽  
Ashok K. Prasad ◽  
Chandrani Mukherjee ◽  
Gaurav Shakya ◽  
Gautam K. Meghwanshi ◽  
...  
Keyword(s):  
Pseudomonas Aeruginosa ◽  
Hydroxyl Groups ◽  
Organic Media ◽  
Secondary Hydroxyl ◽  
Novozyme 435 ◽  
Selective Acylation

Different (±)-4-(3/4-acetoxyaryl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2-ones have been synthesized and subjected to enantioselective deacetylation reactions mediated by different lipases in organic media. Novozyme 435 in tetrahydrofuran:diisopropyl ether was found to be the catalyst of choice for efficient enantioselective deacetylation of dihydropyrimidinones under study. Further, we discovered that lipase isolated from Pseudomonas aeruginosa can be used for selective acylation of secondary hydroxyl groups in nucleosides. This observation can be very useful for selective manipulation of different hydroxyl groups in nucleosides.

Biocatalyst-mediated selective acylation and deacylation chemistry on the secondary hydroxyl/amine groups of nucleosides

2021 ◽  
pp. 1-17
Author(s):  
Amarendra Mohan Khan ◽  
Narinder Kumar Agnihotri ◽  
Vinay Kumar Singh ◽  
Subash Chandra Mohapatra ◽  
Divya Mathur ◽  
...  
Keyword(s):  
Secondary Hydroxyl ◽  
Selective Acylation ◽  
Amine Groups

ChemInform Abstract: Selective Acylation of Aliphatic Alcohols in the Presence of Phenolic Hydroxyl Groups.

ChemInform ◽  
2010 ◽  
Vol 31 (21) ◽  
pp. no-no
Author(s):  
Gowravaram Sabitha ◽  
Basi V. Subba Reddy ◽  
Garudammagari S. Kiran Kumar Reddy ◽  
Jhillu S. Yadav
Keyword(s):  
Aliphatic Alcohols ◽  
Phenolic Hydroxyl ◽  
Hydroxyl Groups ◽  
Selective Acylation ◽  
Phenolic Hydroxyl Groups

Conversion of hydroxyl groups into bromo groups in carbohydrates with inversion of configuration

1981 ◽  
Vol 59 (2) ◽  
pp. 339-343 ◽  
Author(s):  
Björn Classon ◽  
Per J. Garegg ◽  
Bertil Samuelsson
Keyword(s):  
Elevated Temperature ◽  
Hydroxyl Groups ◽  
Secondary Hydroxyl ◽  
Reaction Proceeds ◽  
One Step ◽  
High Yields

A novel reagent system is described for the efficient, one-step transformation of hydroxyl groups in carbohydrates to bromodeoxy groups. The reaction proceeds with inversion of configuration. The reagent system consists of triphenylphosphine, tribromoimidazole, and imidazole in toluene at elevated temperature. The carbohydrate need not be soluble in toluene. The examples given include substitution of isolated primary and secondary hydroxyl groups in otherwise protected carbohydrates as well as disubstitution involving one primary and one secondary position in hexopyranosides. High yields are obtained in the replacement of hydroxyl by bromine in the 2-position of 3,4,6-protected methyl α-D-gluco- and -mannopyranosides.

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