29780-94-7Relevant articles and documents
2,3,4,5-tetra-?-acetyl-1,6-di-?-(triphenylmethyl)-D- mannitol
Shalaby, M. Ashraf,Fronczek, Frank R.,Voll, Ronald J.,Watkins, Steven F.,Younathan, Ezzat S.
, p. 381 - 383 (1996)
The central six-C-atom chain of the title compound, C52H50O10, adopts a nearly planar extended conformation free from C//C, C//O and O//O 1,3-parallel interactions. The three torsion angles formed by these atoms have values of 177.4(2), 174.2(2) and -178.0(2)°. The bulky triphenylmethyl groups, which are oriented gauche to their neighboring acetoxy groups with O-C-C-O torsion angles of -69.8 (2) and -63.0 (2)°, cause no distortion of the bond lengths and bond angles of the sugar moiety.
Synthesis of allo - And epi -inositol via the NHC-catalyzed carbocyclization of carbohydrate-derived dialdehydes
Stockton, Kieran P.,Greatrex, Ben W.,Taylor, Dennis K.
, p. 5088 - 5096 (2014/06/23)
A synthesis of carbocyclic sugars from carbohydrate-derived dialdehydes using organocatalysis has been developed. Sorbitol, mannitol, and galactitol were converted via 1,6-tritylation, perbenzylation or permethylation, detritylation, and Swern oxidation into 2,3,4,5-tetra-O-alkyl-dialdoses that were cyclized via the benzoin reaction promoted by a triazolium carbene. Manno- and galacto-configured dialdehydes gave predominantly single inosose stereoisomers in up to 75% yield if the mixture was acetylated prior to isolation while the gluco-dialdehyde afforded a mixture of three stereoisomers in 61% overall yield. The inososes were stereospecifically reduced using sodium borohydride and then deprotected to give allo- and epi-inositol in good yield that confirmed the structural and stereochemical assignments.
New derivatives of D-mannaric and galactaric acids. Synthesis of a new stereoregular Nylon 66 analog from carbohydrate-based monomers having the D-manno configuration
Mancera, Manuel,Roffe, Isaac,Rivas, Manuel,Galbis, Juan A.
, p. 1115 - 1119 (2007/10/03)
2,3,4,5-Tetra-O-methyl-D-mannaric and galactaric acids and their bis(pentachlorophenyl) esters have been prepared as crystalline compounds, in good yields, from D-mannitol and galactitol, respectively. A new stereoregular polyamide, analogous to Nylon 66,