Stereodivergent approach in the protected glycal synthesis of L-vancosamine, L-saccharosamine, L-daunosamine and L-ristosamine involving a ring-closing metathesis step

• Pierre-Antoine Nocquet,
• Aurélie Macé,
• Frédéric Legros,
• Jacques Lebreton,
• Gilles Dujardin,
• Sylvain Collet,
• Arnaud Martel,
• Bertrand Carboni and
• François Carreaux

Beilstein J. Org. Chem. 2018, 14, 2949–2955, doi:10.3762/bjoc.14.274

• structures 3-amino-2-deoxy sugars [1]. For instance, N,N-dimethyl-L-vancosamine is an essential component of pluramycin antibiotics such as kidamycin and pluramycin A via a C-glycosidic linkage (Figure 1). For constructing aryl C-glycoside bonds, glycal derivatives are versatile synthetic intermediates

Intramolecular glycosylation

• Xiao G. Jia and
• Alexei V. Demchenko

Beilstein J. Org. Chem. 2017, 13, 2028–2048, doi:10.3762/bjoc.13.201

• ). With primary glycosyl acceptors, such as 66 (Scheme 16), yields were slightly diminished due to the formation of the homocoupling products. Secondary alcohol acceptors were even less efficient showing a high substrate specificity of this approach. Other donor series including 2-azido and 2-deoxy sugars

N-Alkyl derivatives of diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside; synthesis and antimicrobial activity

• Agata Walczewska,
• Daria Grzywacz,
• Dorota Bednarczyk,
• Małgorzata Dawgul,
• Andrzej Nowacki,
• Wojciech Kamysz,
• Beata Liberek and
• Henryk Myszka

Beilstein J. Org. Chem. 2015, 11, 869–874, doi:10.3762/bjoc.11.97

• summarized and presented. We have studied different glycosyl donors, different amine group protections, different solvents and promoters to find the best way to obtain 7. The presented compilation is informative for all those interested in the glycosidation of 2-amino-2-deoxy sugars. Results and Discussion

Indium-mediated allylation in carbohydrate synthesis: A short and efficient approach towards higher 2-acetamido-2-deoxy sugars

• Christopher Albler,
• Ralph Hollaus,
• Hanspeter Kählig and
• Walther Schmid

Beilstein J. Org. Chem. 2014, 10, 2230–2234, doi:10.3762/bjoc.10.231

Branching out at C-2 of septanosides. Synthesis of 2-deoxy-2-C-alkyl/aryl septanosides from a bromo-oxepine

• Supriya Dey and
• Narayanaswamy Jayaraman

Beilstein J. Org. Chem. 2012, 8, 522–527, doi:10.3762/bjoc.8.59

• bond formation with alkyl and aryl substituents. Keywords: C–C bond formations; 2-deoxy sugars; organometallic reactions; septanosides; unsaturated sugars; Introduction Septanoses and septanosides are unnatural, seven-membered cyclic sugars [1]. Methods of preparation and the exploration of the

Part 1. Reduction of S-alkyl- thionocarbonates and related compounds in the presence of trialkylboranes/air

• Jean Boivin and
• Van Tai Nguyen

Beilstein J. Org. Chem. 2007, 3, No. 45, doi:10.1186/1860-5397-3-45

• reduction. In this context, the Surzur-Tanner/Giese rearrangement was particularly illustrative. [22][23][24][25] The 2 → 1 migration of the acyloxy group in glycosyl radicals is well documented and allows an easy preparation of 2-deoxy-sugars. At 20°C in 1,2-dichloroethane, a 50/50 mixture of the "regular