Convenient Synthesis of 1,4-Dideoxy-1,4-imino-D-ribitol from D-Ribose

Scheme 1

Synthesis of DRB (1). Reagents and conditions: (i) (COCl)₂, DMF, CH₂Cl₂, 97%; (ii) KOH, H₂O, then, 3 M HCl, quant; (iii) TBSCl, imidazole, CH₂Cl₂, 91%; (iv) NaBH₄, MeOH, 95%; (v) MsCl, pyridine, 85%; (vi) PhCH₂NH₂ (BnNH₂), toluene, 86%; (vii) 1 M HCl, quant; and (viii) H₂, 10% Pd/C, H₂O, quant.