Table 1 Reaction development and the control experimenta

From: Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl ortho−2,2-dimethoxycarbonylcyclopropylbenzoate donors

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Entry

Derivation from standard condition

Yields of 3a (%)

Yields of recovered donor (%)

Yields of 4 (%)

1

None

96

-

99

2

No Sc(OTf)3

0

>95

0

3

Bi(OTf)3 as the catalyst

65

40

58

4

Zn(OTf)2 or Ca(OTf)2/nBu4NPF6 or B(C6F5)3 as catalyst

0

>95

0

5

TfOH as catayst

complex mixture

-

NA

6

TMSOTf as catalyst

<5

>95

<5

7

Ph3PAuNTf2 as catalyst

0

>95

0

8

4 Å MS instead of 5 Å MS

33

68

30

9

CH2Cl2 as the solvent

99

-

99

10

PhCH3 or PhCF3 or Et2O as solvent

96–97

-

>95

11b

glucose pentabenzoate 5 as donor

trace

>95

NA

  1. aUnless otherwise specified, all reactions were performed with 1.2 equiv of 1a, 1.0 equiv of 2a (0.05 mmol) in the presence of the catalyst (0.1 equiv) and 5 Å MS in corresponding solvent (0.05 M, 1 mL) for 2–5 h at room temperature. The yield for 3a was based on 2a, and the yields for 4 and the recovered donor were based on the 1a. bCH2Cl2 was used as the solvent. Bz Benzoyl, Me Methyl, Tf Trifluoromethanesulfonyl, DCE 1,2-dichloroethane, nBu n-Butyl, TMS Trimethylsilyl, Ph Phenyl, MS Molecular sieve, Et Ethyl, NA Not applicable.