7226-27-9Relevant articles and documents
Bio-based aromatic polyesters from a novel bicyclic diol derived from d-mannitol
Lavilla,De Ilarduya, A. Martinez,Alla,Garcia-Martin,Galbis,Munoz-Guerra
, p. 8257 - 8266 (2012)
2,4:3,5-Di-O-methylene-d-mannitol, abbreviated as Manx, is a d-mannitol-derived compound with the secondary hydroxyl groups acetalized with formaldehyde. The bicyclic structure of Manx consists of two fused 1,3-dioxane rings, with two primary hydroxyl gro
Bifunctional acyclic nucleoside phosphonates: synthesis of chiral 9-{3-hydroxy[1,4-bis(phosphonomethoxy)]butan-2-yl} derivatives of purines
Vrbkova, Silvie,Dracinsky, Martin,Holy, Antonin
, p. 2233 - 2247 (2008/02/11)
We report herein a general method for the synthesis of new types of chiral acyclic nucleoside four-carbon bisphosphonates. The alkylation of 2-amino-6-chloropurine and adenine was performed with (2S,3S)- or (2R,3R)-1,4-[bis(diisopropoxyphosphoryl)methoxy]]-3-[(methylsulfonyl)oxy]butan-2-yl benzoate. Alkylations provided (2R,3R) or (2S,3S) N9-substituted nucleobases, which were further converted to other derivatives. These conversions included either a modification of the nucleobase or transformation of the bisphosphonate chain. Subsequent deprotection of the diisopropyl esters with bromotrimethylsilane provided the resulting (2R,3R)- or (2S,3S)-bisphosphonic acids.
Phenylboronic acid as a labile protective agent: the selective derivatisation of 1,2,3-triols
Bhaskar, Vijaya K.,Duggan, Peter J.,Humphrey, David G.,Krippner, Guy Y.,McCarl, Victoria,Offermann, Daniel A.
, p. 1098 - 1102 (2007/10/03)
The ability of phenylboronic acid to act as a labile protective agent for open-chain 1,2,3-triols is demonstrated in the highly selective terminal derivatisation of D-mannitol and an antiviral sialic acid derivative. Protection, derivatisation and deprotection are carried out in a single pot, yielding analytically pure products in moderate yield, without the need for chromatography or formal recrystallisation steps. In both classes of compound, the selectivity of protection is found to be complementary to existing methods, providing access to relatively uncommon 1,6-diesters and the 1,6-bis(benzyl ether) of D-mannitol, and 9-o-acylsialic acid derivatives.