87791-17-1Relevant academic research and scientific papers
Use of N-pivaloyl imidazole as protective reagent for sugars
Santoyo-Gonzalez, Francisco,Uriel, Clara,Calvo-Asin, Jose A.
, p. 1787 - 1792 (2007/10/03)
N-Pivaloyl imidazole was prepared and used as a selective protective reagent of different monosaccharides (D-glucose, D-mannose, D-galactose, 2- acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-β-D-glucopyranosyl azide) and lactose. A variety of pivalates were obtained with moderate or good regioselectivity.
Synthesis and utilization of saccharide intermediates
Becker,Galili
, p. 129 - 141 (2007/10/02)
A new method has been developed for preparation of partially pivaloylated saccharides in one step from readily available starting materials. These intermediates were used in the synthesis of disaccharides and a glucosteroid. A new method has been developed for preparation of partially pivaloylated saccharides in one step from readily available starting materials. These intermediates were used in the synthesis of disaccharides and a glucosteroid.
A novel synthesis of protected glucose intermediates
Becker,Galili
, p. 4775 - 4778 (2007/10/02)
The 1,2,4,6-Tetra-O-pivaloyl-D-gluco-pyranose 3 and 1,2,3,6-Tetra-O-pivaloyl-D-gluco-pyranose 4 have been prepared in one step from anhydrous glucose and pivaloyl chloride. These new intermediates can be converted into the corresponding esters, or used in the synthesis of a disaccharide in good yield. Thus, 2,3,6-Tri-O-pivaloyl-gluco-pyranose 10 can be prepared from 4, and used for preparation of β-gluco derivatives via the corresponding trichloroacetimidate 12.
Syntheses of partially pivaloylated D-glucopyranoses: New substrates for the esterase from rabbit serum
Ljevakovic,Tomic,Tomasic
, p. 107 - 115 (2007/10/02)
The selective pivaloylation (pivaloyl chloride-pyridine) of D-glucopyranose proceeds by two pathways after initial 6-pivaloylation, namely, successive esterification of (a) positions 1, 3, 4, and 2 (major pathway) and (b) positions 2, 1, 4, and 3 (minor pathway). Numerous di- (3 and 4), tri- (5-9), and tetra-pivalates (10-12) have been prepared and characterised. On treatment of the 2,6-dipivalate (4) with rabbit serum or partially purified esterase II, PivO-6 was hydrolysed selectively, whereas the 1,6-dipivalate (3) underwent partial 1 → 2 acyl migration to give 4 and enzymic de-esterification of 3 and 4 occurred simultaneously. The selective pivaloylation (pivaloyl chloride-pyridine) of D-glucopyranose proceeds by two pathways after initial 6-pivaloylation, namely, successive esterification of (a) positions 1, 3, 4, and 2 (major pathway) and (b) positions 2, 1, 4, and 3 (minor pathway). Numerous di- (3 and 4), tri- (5-9), and tetra-pivalates (10-12) have been prepared and characterised. On treatment of the 2,6-dipivalate (4) with rabbit serum or partially purified esterase II, PivO-6 was hydrolysed selectively, whereas the 1,6-dipivalate (3) underwent partial 1→2 acyl migration to give 4 and enzymic de-esterification of 3 and 4 occurred simultaneously.
