Simple exploration of 83-87-4

83-87-4 (3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 10293747, aTetrahydropyrans compound, is more and more widely used in various fields.

83-87-4,83-87-4, (3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate is a Tetrahydropyrans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

1,2,3,4,6-penta-O-acetyl-D-glucopyranose (1.678g, 4.30mmol) dissolved in DCM (10.75mL) was added hydrogen bromide (33% in acetic acid, 2.97mL) dropwise at 0C. The reaction mixture was then allowed to warm to room temperature and stir for an additional 4h. The reaction was quenched with water and the aqueous layer was extracted with DCM. The organic layers were combined and washed with water, saturated aqueous NaHCO3, brine, and then dried with sodium sulfate and concentrated under reduced pressure to afford a clear viscous oil that was immediately added to a biphasic mixture of diphyllin (1.090g, 2.87mmol) and TBAB (0.933g, 2.89mmol) in CHCl3 (100mL) and aqueous NaOH (0.1M, 100mL) at 40C. The mixture was maintained at 40C overnight. After cooling to room temperature, the layers were separated and the aqueous layer was extracted three times with CHCl3. The combined organic layers were washed with brine, dried with sodium sulfate, and concentrated under reduced pressure. Flash chromatography (silica gel, 0.3%?1% MeOH in CHCl3) afforded compound 8a (1.928g, 95%) as a white solid:

83-87-4 (3R,4S,5R,6R)-6-(Acetoxymethyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 10293747, aTetrahydropyrans compound, is more and more widely used in various fields.

Reference£º
Article; Woodard, John L.; Huntsman, Andrew C.; Patel, Pratiq A.; Chai, Hee-Byung; Kanagasabai, Ragu; Karmahapatra, Soumendrakrishna; Young, Alexandria N.; Ren, Yulin; Cole, Malcolm S.; Herrera, Denisse; Yalowich, Jack C.; Kinghorn, A. Douglas; Burdette, Joanna E.; Fuchs, James R.; Bioorganic and Medicinal Chemistry; vol. 26; 9; (2018); p. 2354 – 2364;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics