Highly stereoselective Grignard reaction of an aldopyranose: A simple synthesis of 6-deoxy-D-idose from D-xylose.

Synthesis, crystal structure, and reactivity of a d-xylose based oxepine

“…3,4,5-tri-O-benzyl-D D -xylose was synthesized by the route of Tsuda et al 20 Into a flame dried round-bottom flask was added methyl triphenylphosphonium bromide (4.46 g, 12.5 mmol) and dry THF (30 mL) to make a white suspension, which was cooled to 0°C on an ice bath. n-Butyllithium O …”

“…Access to 21 suggests that it too may be used as a glycosyl donor in the preparation of additional septanosides. In all the examples (11,12,(15)(16)(17)(18)(19)(20)(21), the C-2 alcohol can also be selectively functionalized.…”

Synthesis and Evaluation of Lipophilic Aza‐C‐glycosides as Inhibitors of Glucosylceramide Metabolism

“…Starting from the D ‐xylose ( 57 ) derived 58 , the D ‐ xylo α‐allyl‐aza‐C‐glycoside 62 was synthesized by a similar sequence of reactions as described for 55 . Except now amino alcohol 60 , obtained from a stereoselective43 Grignard reaction on 59 , was cyclized to 61 by an intramolecular Mitsunobu reaction 44,45…”

Total syntheses of bioactive natural products from carbohydrates

“…The stereoselective synthesis of (À)-rosmarinecine (42) was converted to the triol 51, which contained already felicitously placed functional groups and an anomeric carbon of potential value for the stereoselective introduction of hydroxyl groups and carbon chain. Silylation to protect primary alcohols of 51 gave the corresponding disilyl furanoside, which was submitted to Grignard reaction with allylmagnesium bromide in ether to afford the single threo amimo alcohol 52 by chelation control approach [66,67]. Further manipulation of 52 gave (À)-rosmarinecine (42) through the lactam 53.…”