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. Author manuscript; available in PMC: 2021 Apr 16.
Published in final edited form as: Angew Chem Int Ed Engl. 2020 Feb 25;59(16):6451–6458. doi: 10.1002/anie.201915913

Table 1.

Investigation of the impact of protective groups on β-selective di-aminofucosylation.

graphic file with name nihms-1552194-t0002.jpg
Entry Substrate Reaction Condition Yield α : β
1 graphic file with name nihms-1552194-t0003.jpg [p-TolSCl + AgOTf]a, DCM 89% 3 : 2
2 graphic file with name nihms-1552194-t0004.jpg [NIS + TfOH]b, DCM 92% 2 : 3
3 graphic file with name nihms-1552194-t0005.jpg [NIS + TfOH], DCM/MeCN = 9/1 90% 2 : 3
4 graphic file with name nihms-1552194-t0006.jpg [NIS + TfOH], DCM/MeCN = 1/1 25% α only
5 graphic file with name nihms-1552194-t0007.jpg [NIS], DCM 60% 5 : 1
6 graphic file with name nihms-1552194-t0008.jpg [NIS], DCM <5% N/A
7 graphic file with name nihms-1552194-t0009.jpg [p-TolSCl + AgOTf], DCM 30% α only
8 graphic file with name nihms-1552194-t0010.jpg [NIS + TfOH], DCM 80% 3 : 1
9 graphic file with name nihms-1552194-t0011.jpg [NIS + TfOH], DCM 91% 1 : 2
10 graphic file with name nihms-1552194-t0012.jpg [NIS + TfOH], DCM <5% N/A
11 graphic file with name nihms-1552194-t0013.jpg [p-TolSCl + AgOTf], DCM 60% 1 : 2.5c
[a]

[NIS + TfOH]: NIS, TfOH, 4Å MS, −78°C

[b]

[p-TolSCl + AgOTf]: p-TolSCl, AgOTf, 4Å MS, −78°C

[c]

Ratios determined from NMR spectra of the crude reaction mixtures