The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation

• Rituparna Das and
• Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2025, 21, 369–406, doi:10.3762/bjoc.21.27

• Rituparna Das Balaram Mukhopadhyay SWEET Lab, Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Kolkata, Mohanpur, Nadia 741246, India 10.3762/bjoc.21.27 Abstract Stereoselective glycosylations are one of the most challenging tasks of synthetic

Total synthesis of the O-antigen repeating unit of Providencia stuartii O49 serotype through linear and one-pot assemblies

• Tanmoy Halder and
• Somnath Yadav

Beilstein J. Org. Chem. 2021, 17, 2915–2921, doi:10.3762/bjoc.17.199

• stereoselective glycosylations. The work provides an access to the trisaccharide repeating unit of the O-polysaccharide of Providencia stuartii O49 with the stereospecific α-p-methoxyphenyl glycoside. Structure of the repeating unit of the lipopolysaccharide of Providencia stuartii O49 serotype. Retrosynthetic

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

Convergent synthesis of the pentasaccharide repeating unit of the biofilms produced by Klebsiella pneumoniae

• Arin Gucchait,
• Angana Ghosh and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2019, 15, 431–436, doi:10.3762/bjoc.15.37

• using a set of stereoselective glycosylations of a number of suitably functionalized monosaccharide derivatives 2, 3 [14], 4, 5 [15], 6 [16] and 7 [17], which were prepared from the commercially available reducing monosaccharides using a number of functional group manipulations reported earlier (Figure

TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals

• Mei-Yuan Hsu,
• Yi-Pei Liu,
• Sarah Lam,
• Su-Ching Lin and
• Cheng-Chung Wang

Beilstein J. Org. Chem. 2016, 12, 1758–1764, doi:10.3762/bjoc.12.164

• and high susceptibility to hydrolysis, which are the main obstacles to constructing glycosidic linkages stereoselectively [8]. Some approaches, such as the AgPF6-DTBMS [9] and preactivation approach [10], can directly yield stereoselective glycosylations. Indirect methods that utilize auxiliary groups

Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols

• Tamashree Ghosh,
• Abhishek Santra and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2013, 9, 974–982, doi:10.3762/bjoc.9.112

• ][2][3][4][5]. Due to their thermal and chemical stability, they have been used as stable intermediates for functional-group transformations as well as stereoselective glycosylations. Thioglycosides can be transformed into various other glycosyl donors [6][7][8][9][10] (e.g., sulfoxide, sulfone

Acceptor-influenced and donor-tuned base-promoted glycosylation

• Stephan Boettcher,
• Martin Matwiejuk and
• Joachim Thiem

Beilstein J. Org. Chem. 2012, 8, 413–420, doi:10.3762/bjoc.8.46

• ; however, regioselective and stereoselective glycosylations remain difficult and alternative concepts are welcome, and should be considered and studied. Recently regioselective and β-stereospecific glycosylations employing saccharide oxyanions have been presented. Initial studies on base-promoted

Benzyne arylation of oxathiane glycosyl donors

• Martin A. Fascione and
• W. Bruce Turnbull

Beilstein J. Org. Chem. 2010, 6, No. 19, doi:10.3762/bjoc.6.19

• ; stereoselective glycosylations; Introduction Carbohydrates play important roles in many biological processes including tumour metastasis [1][2], bacterial and viral recognition [3][4][5], and the immunological response [6][7][8]. In order to obtain pure samples of oligosaccharides for biological studies

• -stereoselective glycosylations. b) Modified strategy for stereoselective glycosylations using oxathiane ketal glycosyl donors 5. Benzyne generation from 1-ABT. Oxathiane donor synthesis. Arylation/acetate glycosylation of oxathiane glycosyl donors. Supporting Information Supporting Information File 1 features