Details

Autor(en) / Beteiligte

• Lloyd, Dina
• Bennett, Clay S.

Titel

An Improved Approach to the Direct Construction of 2‐Deoxy‐β‐Linked Sugars: Applications to Oligosaccharide Synthesis

Ist Teil von

• Chemistry : a European journal, 2018-05, Vol.24 (30), p.7610-7614

Ort / Verlag

Germany: Wiley Subscription Services, Inc

Erscheinungsjahr

2018

Link zum Volltext

Quelle

Wiley Online Library Journals Frontfile Complete

Beschreibungen/Notizen

• A next‐generation reagent‐controlled approach for the synthesis of 2,6‐dideoxy and 2,3,6‐trideoxy sugar donors in good yield and high β‐selectivity is reported. The use of p‐toluenesulfonyl chloride and potassium hexamethyldisilazide (KHMDS) greatly simplifies deoxy‐sugar glycoside construction, and can be used for gram‐scale glycosylation reactions. The development of this approach and its application to the construction of β‐linked deoxy‐sugar oligosaccharides are described. β‐max! An improved protocol for the direct synthesis of β‐linked deoxy‐sugars is described. A combination of p‐toluenesulfonyl chloride and potassium hexamethyldisilazide (KHMDS) can activate hemiacetal glycosyl donors for dehydrative glycosylations that can be performed on scales of up to several grams. The application to oligosaccharide synthesis is described.