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. Author manuscript; available in PMC: 2016 Aug 19.
Published in final edited form as: J Am Chem Soc. 2015 Aug 7;137(32):10336–10345. doi: 10.1021/jacs.5b06126

Table 4.

O-Mannosylation with Donor 18.

Entry Nucleophile Equiv (M conc) β-gly/cycl α-gly/cycl
40/(30+31)c 41/(30+31)c
1a iPrOH 1 (0.019) 0.27 0.27
2a iPrOH 2 (0.038) 0.95 0.85
3a iPrOH 2.5 (0.048) 1.11 1.08
4a iPrOH 3 (0.057) 1.27 1.20
5a iPrOH 4 (0.076) 1.60 1.39
6a iPrOH 5 (0.095) 1.75 1.67
7a iPrOH 7.5 (0.143) 1.84 1.73
8a iPrOH 10 (0.190) 1.87 1.78
a

Experimental conditions: TTBP (10 equiv), β-pinene (30 equiv), molecular sieves 4 Å, Tf2O (1.2 equiv) at − 60 °C;

b

Molar ratios were determined by UHPLC/UV/MS