1,2-O-Isopropylidene-a-D-glucofuranose

A novel synthesis of D-glucose 6-phosphate (in 55% yield) has been reported it involves alcoholysis of the cyclic phosphate of catechol with 1,2-O-isopropylidene-a-D-glucofuranose, followed by acid hydrolysis of the so-formed phosphoric diester.192 The reagent... 

In contrast to the oxidation of acyclic polyhydric alcohols in benzene,508 treatment of 1,2-O-isopropylidene-a-D-glucofuranose with silver carbonate-on-Celite in boiling methanol led to selective oxidation of the primary hydroxyl group, with the formation of the al-duronic acid derivative in 68% yield.517... 

Bakke and Theander132 described an interesting, new synthesis of L-ascorbic acid by one-step oxidation of 1,2-O-isopropylidene-a-D-glucofuranose to l,2-0-isopropylidene-a-D-xyfo-5-hexulofuranurono-6,3-lactone hydrate (74), followed by hydrolysis of the isopropyli-dene group, and specific, borohydride reduction of the aldehyde group liberated. 

Hydrolysis of 5,6-anhydro-l,2-0-isopropylidene-a-D-glucofuranose with sodium hydroxide under controlled conditions can lead71-74 to both 3,5-anhydro-l,2-0-isopropylidene-/3-L-idofuranose and 3,6-anhydro-l,2-0-isopropylidene-a-D-glucofuranose, in addition to 1,2-O-isopropylidene-a-D-glucofuranose (see p. 130), whereas mild hydrolysis with 5 mM sulfuric acid can give up to 25% of 2,5-anhydro-L-idose (62), besides the expected D-glucose.195 This reaction must in-... 

An alternative synthesis468 of L-idonic acid is shown in Scheme 15. On oxidation with periodate, 1,2-O-isopropylidene-a-D-glucofuranose (56) yields the protected dialdose 91. When 91 is treated with hydrogen cyanide, a mixture (92) of the Q-gluco and L-tdo nitriles results, with the D-gluco nitrile preponderating. Hydrolysis affords L-iduronic... 

O-isopropylidene-a-D-glucofuranose by zinc methoxypropanol complex catalyst, J. Polym. Sci., Part A Polym. Chem., 22 (1984) 3593-3598. 

D. Horton and J.-H. Tsai, Preparation of derivatives of L-idose and L-iduronic acid from 1,2-O-isopropylidene-a-D-glucofuranose by way of acetylenic intermediates, Carbohydr. Res., 58 (1977) 89-108. 

Free Sugars and Simple Derivatives Thereof. — jJ-D-Arabinopyranose (n.d.), jJ-D-lyxopyranose (n.d.), 3-D-xylopyranose tetrabenzoate and 1,5-anhydro-2,3,4-tri-O-benzoylxylitol, a-D-glucopyranose (a refinement based on previously published n.d. data), 1,2-O-isopropylidene-a-D-glucofuranose, a-L-sorbopyranose (n.d.), d-deoxy-a-L-sorbofuranose," and a-D-mawno-heptulo-pyranose. ... 

Benzoyl, 5,6-di-Ac 5,6-Di-0-acetyl-3-O-benzoyl-1,2-O-isopropylidene-a-D-glucofuranose C20H24O9 408.404 Mp 77-78°. [ ]d -26.7 (CHCI3). 

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