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. 2019 Feb 1;84(5):2415–2424. doi: 10.1021/acs.joc.8b02613

Table 2. Reaction of Glycals 9ad and 11ac with Model Glycosyide Acceptors 2a, 2e, or 2g.

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entry R1 R2 R3 product time (h) yield (%)a α/βb
1 9a Bn Bn Bn 10a 1 88d,e 21:1
2 9a Bn Bn Bn 10c 1 94 26:1
3 9a Bn Bn Bn 10e 2 84 30:1
4 9a Bn Bn Bn 10g 7 62 25:1
5 9a Bn Bn Bn 10h 7 68 20:1
6 9b TBS TBS TBS 11b 1 92 30:1
7 9c MOM MOM MOM 11c 1 71 20:1
8 9d Si(tBu)2 MOM 11d 1 82 20:1
9 11a Bn Bn Bn 12ac 17 54 30:1
10 11b O[Si(i-Pr)2]2 Bn 12b 17 78 30:1
11 11c O[Si(i-Pr)2]2 TIPS 12c 17 75 30:1
12 11c O[Si(i-Pr)2]2 TIPS 13 17 86 30:1
13 11c O[Si(i-Pr)2]2 TIPS 14 17 64 20:1
a

Isolated yield.

b

Determined by 1H NMR.

c

10% Ferrier product 12a′ also isolated.

d

Reaction did not proceed in the absence of catalyst.

e

Reaction with BF3.OEt2 afforded 10a (<35%) and a mixture of products and starting material.