195533-35-8

Upstream product

• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 2873-29-2 D-glucal triacetate 

Downstream Products

• 195533-47-2 [(2R,3S,6S)-3-(2-Bromo-allyloxy)-6-((E)-3-phenyl-allyloxy)-3,6-dihydro-2H-pyran-2-ylmethoxy]-tert-butyl-dimethyl-silane 
• 195533-40-5 (2R,3S,6S)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-6-((E)-3-phenyl-allyloxy)-3,6-dihydro-2H-pyran-3-ol 
• 1025985-01-6 (2R,3S,6S)-2-Hydroxymethyl-6-((E)-3-phenyl-allyloxy)-3,6-dihydro-2H-pyran-3-ol 

Relevant academic research and scientific papers

CeCl3·7H2O: A novel reagent for the synthesis of 2-deoxysugars from D-glycals

D-Glycals react smoothly with a variety of alcohols in a highly stereoselective manner in the presence of the CeCl3·7H2O-NaI reagent system in refluxing acetonitrile under neutral conditions to afford the corresponding 2-deoxy-α-glycopyranosides in high yields. In the absence of NaI, the glycals undergo Ferrier rearrangement under the influence of CeCl3·7H2O in refluxing acetonitrile to afford the corresponding 2,3-unsaturated hexopyranosides in good yields.

Scandium triflate catalyzed ferrier rearrangement: An efficient synthesis of 2,3-unsaturated glycopyranosides

Scandium(III) trifluoromethanesulfonate is found to catalyze efficiently the O-glycosidation of 3,4,6-tri-O-acetyl-D-glucal with various alcohols and phenols to afford the corresponding 2,3-unsaturated glycosides in excellent yields with good anomeric selectivity.

Palladium-Mediated Cyclization on Carbohydrate Templates. 2. Synthesis of Enantiopure Tricyclic Compounds

The bromo substituted unsaturated carbohydrates 3a-f were prepared from 3,4,6-tri-O-acetyl-D-glucal by Ferrier reaction with the appropriate allylic or homoallylic alcohol, deacetylation followed by monosilylation with TBDMSC1, and then alkylation with BrCH2CBr=CH2. The N- and C-analogues 4a,b were synthesized by palladium alkylation of the intermediate carbonate with TsNHCH2CBr=CH2 and (MeO2C)2,CHCH2CBr=CH2) respectively. Treatment of the unsaturated carbohydrates 3a, 4a, and 4b with a catalytic amount of Pd(OAc)2/PPh3 in CH3CN/H2O, in the presence of Bu4NHSO4 and NEt3, afforded the tricyclic compounds 5, 6, and 7, respectively. Under the same conditions, the analogue tricyclic compounds 8, 9, and 10 were formed starting from 3b-d. In the case of compounds 3e and 3f, the formation of the bicyclic glucal 11 via an already described β-alkoxyelimination was only observed. Moreover, trapping of the σ-alkylpalladium intermediate obtained from 3e with an external nucleophile yielded the 2-deoxy carbohydrate 12 and the 2,3-unsaturated sugar 13, using respectively sodium formate and sodium tetraphenylborate.