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. Author manuscript; available in PMC: 2012 Apr 15.
Published in final edited form as: J Org Chem. 2011 Mar 18;76(8):2532–2547. doi: 10.1021/jo102382r

TABLE 4.

Facioselectivities of dideoxypentenoside epoxidation by DMDO

dideoxypentenoside react conda epoxide α:β
graphic file with name nihms281802t33.jpg 20 A graphic file with name nihms281802t34.jpg 20:1
graphic file with name nihms281802t35.jpg 21 A graphic file with name nihms281802t36.jpg 10:1b
graphic file with name nihms281802t37.jpg 26 A graphic file with name nihms281802t38.jpg 2:3
graphic file with name nihms281802t39.jpg 27 A graphic file with name nihms281802t40.jpg <1:2
graphic file with name nihms281802t41.jpg xylal (28) A graphic file with name nihms281802t42.jpg 5:1
B 4:1c
graphic file with name nihms281802t43.jpg arabinal (29) A graphic file with name nihms281802t44.jpg >20:1
a

Reaction conditions: (A) DMDO (3 equiv), −55 °C, 2 days; (B) DMDO (2 equiv) 0 °C, 1 hour.

b

Ref. 10.

c

Ref. 7.