Synthesis of Lacto-N-neohexaose and Lacto-N-neooctaose Using the Dimethylmaleoyl Moiety as an Amino Protective Group
✍ Scribed by Mohamed R. E. Aly; El-Sayed I. Ibrahim; El-Sayed H. E. El-Ashry; Richard R. Schmidt
- Publisher
- John Wiley and Sons
- Year
- 2000
- Tongue
- English
- Weight
- 410 KB
- Volume
- 2000
- Category
- Article
- ISSN
- 1434-193X
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✦ Synopsis
The N-DMM-Protected lactosamine derivative 2 was readily neohexaose). Glycosylation of acceptor 10 with donor 4 furnished tetrasaccharide 16 which, employing standard transformed into the corresponding glycosyl donor 4 and into acceptor 5. A TMSOTf-catalyzed glycosidation afforded the procedures, gave acceptor 18. Glycosylation of 18 with donor 9 furnished, under standard conditions, octasaccharide 19. derived tetrasaccharide 6 which led to glycosyl donor 9. Reaction of 9 with lactose derivative 10 as acceptor gave the Cleavage of all protective groups and N-acetylation afforded the target molecule 1c (lacto-N-neooctaose). Both 1b and 1c desired hexasaccharide 11. Cleavage of all protective groups and N-acetylation afforded the target molecule 1b (lacto-N-were obtained in good overall yields.
taining the dimethylmaleoylamido group could also be gen-