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. 2018 Mar 19;140(13):4632–4638. doi: 10.1021/jacs.8b00669

Scheme 4. Stereoselective Synthesis of Branched Alpha Nonasaccharide 1.

Scheme 4

(a) TMSI, Ph3P=O, DCM, rt, 27: 91%, α:β = 11:1; 32: 68%; 44: 67%. (b) 0.2 M HCl/HFIP, DCM/HFIP, 28: 85%; 31: 85%; 33: 83%; 43: 88%. (c) TMSOTf, DMF, 0 °C, 30: 81%. (d) TfOH, DMF, 0 °C, 34: 81%; 36: 91%; 38: 93%; 40: 91%; 42: 80%. (e) DDQ, DCM/H2O, 35: 84%; 37: 75%; 39: 66%; 41: 70%. (f) Pd(OH)2/C, H2 (3.5 atm), THF/H2O/t-BuOH, 61%.