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. Author manuscript; available in PMC: 2013 Sep 12.
Published in final edited form as: J Am Chem Soc. 2012 Aug 31;134(36):14746–14749. doi: 10.1021/ja307266n

Table 2.

C-Glycosylation in competition with cyclization

graphic file with name nihms403797u2.jpg
Entrya TMSCH2C(Me)=CH2b 11/(5+6)c
1 2 (0.034) 0.06
2 4 (0.068) 0.18
3 8 (0.136) 0.40
4 12 (0.204) 0.55
5 15 (0.255) 0.69
6 20 (0.34) 0.87
7 30 (0.51) 1.40
a

Experimental conditions: TTBP (4 equiv), molecular sieves 4 Å, Tf2O (1.2 equiv) at − 72 °C;

b

equiv (conc, M);

c

Molar ratios were determined by UHPLC/UV/MS