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. Author manuscript; available in PMC: 2018 Jun 16.
Published in final edited form as: J Org Chem. 2017 Jun 2;82(12):6142–6152. doi: 10.1021/acs.joc.7b00746

Table 1.

Glycosylation Reactions

graphic file with name nihms881523u4.jpg
Entry Acceptor Product % Yield, α:β ratio 3JCH (Hz)
1 BnOH graphic file with name nihms881523t1.jpg
30
96%, α-only 30: 7.2
2 graphic file with name nihms881523t2.jpg
27
graphic file with name nihms881523t3.jpg
31αβ
87%, 6.7:1 31α: 6.4
3 graphic file with name nihms881523t4.jpg
26
graphic file with name nihms881523t5.jpg
32α,β
82%, 4.4:1 32α: 6.9
4 graphic file with name nihms881523t6.jpg
28
graphic file with name nihms881523t7.jpg
33α,β
75%, a4.5:1 33α: 7.2
33β: 0
5 graphic file with name nihms881523t8.jpg
29
graphic file with name nihms881523t9.jpg
34α,β
88%, 34α:34β:35α= 4.7:1:0.9 34α: 7.0
graphic file with name nihms881523t10.jpg
35
35α: 6,3
6 1-adamantanol graphic file with name nihms881523t11.jpg
36α,β
73%, 4.2:1 36α: 5.7
a

Glycosylation gave an 84% yield of an inseparable 4.5:1 α:β mixture of the disaccharides, which was saponified to give the products 33α and 33β.