Synthesis of the Anomers of Hepta‐O‐acetylcellobiosyl, ‐lactosyl, ‐maltosyl, and ‐melibiosyl Azide Synthesis and characterization by 13C‐NMR spectroscopy of the O‐acetylated 1,2‐cis and 1,2‐trans azides of cellobiose, lactose, maltose, and melibiose have been accomplished. 1,2‐trans Azides 1c, 2b–4b result from the stannic chloride catalyzed reaction of the β‐octa‐O‐acetates 1a–4a with trimethylsilyl azide, whereas the β‐chlorohepta‐O‐acetyldisaccharides 1d, 2c–4c afford, in an SN2 reaction in HMPT with lithium azide, the hitherto inaccessible 1,2‐cis azides 1e, 2d–4d.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry