Toward the synthesis of fine chemicals from lactose: preparation of D-xylo and L-lyxo-aldohexos-5-ulose derivatives.
نویسندگان
چکیده
The transformation of (5R)-2,6-di-O-benzyl-5-C-methoxy-beta-D-galactopyranosyl-(1-->4)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (8) into partially protected derivatives of D-xylo- and L-lyxo-aldohexos-5-ulose has been reported, applying appropriate epimerisation methods to its 3'-O- and 4'-O-protected alcoholic derivatives.
منابع مشابه
Useful access to enantiomerically pure protected inositols from carbohydrates: the aldohexos-5-uloses route
The intramolecular aldol condensation of aldohexos-5-ulose derivatives of the D-xylo and L-ribo stereoseries has been studied. Only one of the four possible inososes was isolated from both stereoseries in reasonable yields (30-38%). The results obtained, together with the previous findings for the L-arabino and L-lyxo stereoseries, allowed for the rationalisation of a mechanism of the reaction ...
متن کاملATTEMPTED SYNTHESIS OF 5' - DEOXY - 5' - PHOSPHONO - ISOCYTIDINE SYNTHESIS OF PHOSPHONIC ACID DERIVATIVES OF ACYCLO - NUCLEOSIDES. PREPARATION OF 1- ?- D- ARABINOFURANOSYL PYRIMIDINES
The synthesis of 5' - deoxynucleoside 5' - phosphonates which contains a 5' - CP bond in place of the 5' -COP bond of the naturally occuring nucleotides is described. The preparation of phosphonate derivatives of acyclo - nucleosides and a simple method for the conversion of 1-? -D-ribofuranosyl pyrimidines to the corresponding 1-? -D-arabinofuranosyl pyrimidines are also explained
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The synthesis of 3,5-di-O-benzyl-D-pinitol has been stereoselectively accomplished through intramolecular aldolization of 2,6-di-O-benzyl-4-O-methyl-L-lyxo-hexos-5-ulose followed by reduction with NaBH(OAc)3. Computational analysis [DFT calculations at the B3LYP/6-31G(d) level] suggests that D-pinitol in water largely prefers the conformation corresponding to the C4 one of a α-L-rhamnopyranosid...
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Pyrano [2,3-d] pyrimidinone derivatives have received considerable interest from the pharmaceutical industry due to their wide range of interesting biological and therapeutic properties. Nano Al2O3 was found to be a highly efficient solid acid catalyst for the preparation of pyrano [2,3-d] pyrimidinone derivatives from the reaction of barbituric acid, aryl aldehyde and mal...
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ورودعنوان ژورنال:
- Carbohydrate research
دوره 344 6 شماره
صفحات -
تاریخ انتشار 2009