Abstract
The reactions of diazomethane with methyl 4,6- O-benzylidene-3-deoxy-3- C-ethyl-α- D- arabino- and - ribo-hexopyranosid- 2-uloses ( 1 and 2) afford spiro-epoxides preponderantly, whereas the corresponding reactions of 1 and 2 with diazoethane give, exclusively, ring-expansion products. Compound 1 gives, preponderantly, heptoseptanosid-3-uloses with diazoethane and not the expected heptoseptanosid-2-uloses, thereby indicating that the nature of the ring-expansion products is controlled by steric rather than by electronic effects. It is shown that comparisons of pyranosid-ulose-diazoalkane reactions can provide new information about the stereochemical course of diazoalkane ring-expansion reactions. The reactions of 1 and 2 with diazoethane provide a route to higher sugars containing two R-C-H branch points.
Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a callDisclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.
