ISSN:
0009-2940
Keywords:
Chemistry
;
Inorganic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Description / Table of Contents:
Branched Chain Sugars, II. Synthesis of L-Streptose and D-HamameloseReaction of 5-deoxy-1,2-O-isopropylidene-β-L-threo-pentofuranos-3-ulose (5) with 2-lithio-1,3-dithiane (2) gives the branched chain sugar 6. Mercuric oxide and boron trifluoride etherate hydrolyze 6 to 5-deoxy-3-C-formyl-1,2-O-isopropylidene-β-L-lyxofuranose (8). Acid hydrolysis of 8 yields L-streptose (9 + 10). Methyl 3,4-O-isopropylidene-β-D-erythro-pento-pyranosid-2-ulose (16) reacts with 2-lithio-1,3-dithiane (2) to form the dithiane sugar 17 which is hydrolyzed to the formyl sugar 19. 19 is converted by reduction and hydrolysis to methyl D-hamameloside (21). Synthesis of further branched chain 1,6-anhydrohexopyranoses is reported.
Notes:
5-Desoxy-1.2-O-isopropyliden-β-L-threo-pentofuranos-3-ulose (5) reagiert mit 2-Lithio-1.3-dithian (2) zum verzweigten Zucker 6, der mit BF3/HgO in 5-Desoxy-3-C-formyl-1.2-O-isopropyliden-β-L-lyxofuranose (8) gespalten werden kann. Saure Hydrolyse von 8 liefert L-Streptose (9 + 10). Methyl-3.4-O-isopropyliden-β-D-erythro-pentopyranosid-2-ulose (16) reagiert mit 2-Lithio-1.3-dithian (2) zum Dithian-Zucker 17, dessen Spaltung den Formyl-Zucker 19 ergibt, der durch Reduktion und Hydrolyse in Methyl-D-hamamelosid (21) übergeführt werden kann. Die Darstellung weiterer verzweigter 1.6-Anhydro-hexopyranosen wird beschrieben.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/cber.19721050623
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