712. The reaction between 3,4,6-tri-O-acetyl-D-glucal and p-nitrophenol

Abstract

+0-44" +0.29" -0.03" (const.) Compound (11) (c 0.6) Time (hr.

Hybrids of sugars and aromatics: A Pd-catalyzed modular approach to chromans and isochromans

“…Starting from 2-bromoglucal 27, 2-bromogalactal 31 and diynols of type 23 we were able to make use of a Lewis-acid promoted Ferrier reaction resulting in a shift of the C@C double bond in the six-membered ring (Scheme 11). 23 We tried different amounts of BF 3 -etherate. It turned out that stoichiometric amounts of Lewis acid at room temperature and a long reaction time (20 h) are essential for a successful reaction.…”

Synthesis and anti-inflammatory activity of N-phthalimidomethyl 2,3-dideoxy- and 2,3-unsaturated glycosides

“…6 In our experiments, N-phthalimidomethyl 2,3-unsaturated sugars 3a, 3b, and 9 were synthesized through nucleophilic addition of N-hydroxymethyl phthalidomide 1 to 3,4,6-tri-O-acetyl-D D-galactal 2a, 3,4,6-tri-O-acetyl-D D-glucal 2b, or 3,6,2 0 ,3 0 ,4 0 6 0 -hexa-Oacetyl-D D-lactal 8 in the presence of boron trifluoride etherate, resulting in a Ferrier rearrangement (Scheme 1). 7 Although it is known that the 2,3-unsaturated sugars formed by this reaction are usually obtained as an anomeric mixtures, only the a-anomer was obtained in our work. The anomeric configurations of compound 3a, 3b, and 9 were confirmed by NMR spectroscopy.…”

Super‐Fluorinated Liquid Crystals: Towards the Limits of Polarity

“…There are several examples for chiral, THP-based liquid crystals where the synthesis starts from natural, chiral pool carbohydrate precursors. The methods reported so far for the preparation of liquid crystals based on racemic THP [11][12][13][14] often have only a rather limited structural scope.…”