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. 2017 Sep 21;139(40):14041–14044. doi: 10.1021/jacs.7b08898

Table 2. Reaction of Glycals 1b1f, 4a, 4b and 5 with Model Glycoside Acceptor 2a.

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entry R1 R2 R3 product (time (h)) yield (%)a α:βb
1 1b Bn Bn Ac 6b (0.7) 94 >30:1
2 1c Bn Bn TIPS 6c (3) 65 6:1
3 1d MOM MOM MOM 6d (6) 76 >30:1
4 1e TBS TBS TBS 6e (2) 78 >30:1
5 1f Ac Ac Ac 6f (−) N/A
6 4a O[Si(i-Pr)2]2 Bn 7a (3) 78 >30:1
7 4b O[Si(i-Pr)2]2 TIPS 7b (2) 83 >30:1
8 5 O[Si(i-Pr)2]2 8 (1) 91 5:1
a

Isolated yield.

b

Determined by 1H NMR. N/A = not applicable.