D-Streptamine, O-5-amino-5,6-dideoxy-β-D-allofuranosyl-(1→5)-O-[2-amino-2,7-dideoxy-D-glycero-α-D-gluco-heptopyranosyl-(1→4)]-2-deoxy- synthesis

Yield:-

Steps:

Multi-step reaction with 10 steps
1.1: magnesium sulfate / (1S)-10-camphorsulfonic acid / acetone / 5 h / 20 °C
2.1: magnesium sulfate; Dess-Martin periodane / dichloromethane / 8 h / 20 °C
3.1: tetrahydrofuran / 2.5 h / -30 °C
4.1: pyridine / dmap / 0 - 20 °C
5.1: N,N,N,N,N,N-hexamethylphosphoric triamide; sodium azide / N,N-dimethyl-formamide / 20 - 70 °C
6.1: water; acetic acid / 70 °C
7.1: pyridine / dmap / 0 - 20 °C
8.1: N-Bromosuccinimide / water; acetone / -30 °C
8.2: 0 °C
9.1: dichloromethane / 0.17 h / -20 °C / 4 ? Molecular sieve
9.2: 1 h / -15 °C
10.1: ethanol; methylamine / 8 h
10.2: 0.17 h / 20 °C

References:

WO2012/66546,2012,A1