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Stereoselective synthesis of 2-deoxy-β-C-aryl/alkyl glycosides using Prins cyclization: Application in the synthesis of C-disaccharides and differently protected C-aryl glycosides.
Carbohydr Res. 2018 Oct; 468:64-68.CR

Abstract

2-Deoxy-β-C-aryl/alkyl glycosides were synthesized from di-O-pivaloyl protected homoallylic alcohol derived from D-mannitol with various aldehydes via the Prins cyclization. The salient features of this methodology are high yields and excellent stereoselectivity. This method has also been successfully applied to the synthesis of differently protected 2-deoxy-β-C-aryl glycosides and C-disaccharides. One of the 2-deoxy-β-C-aryl glycosides was utilized as a glycosyl acceptor in the glycosylation to synthesize an O-linked disaccharides.

Authors+Show Affiliations

Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016, India.Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016, India.Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016, India.Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016, India. Electronic address: vankar@iitk.ac.in.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

30153553

Citation

Dubbu, Sateesh, et al. "Stereoselective Synthesis of 2-deoxy-β-C-aryl/alkyl Glycosides Using Prins Cyclization: Application in the Synthesis of C-disaccharides and Differently Protected C-aryl Glycosides." Carbohydrate Research, vol. 468, 2018, pp. 64-68.
Dubbu S, Chennaiah A, Verma AK, et al. Stereoselective synthesis of 2-deoxy-β-C-aryl/alkyl glycosides using Prins cyclization: Application in the synthesis of C-disaccharides and differently protected C-aryl glycosides. Carbohydr Res. 2018;468:64-68.
Dubbu, S., Chennaiah, A., Verma, A. K., & Vankar, Y. D. (2018). Stereoselective synthesis of 2-deoxy-β-C-aryl/alkyl glycosides using Prins cyclization: Application in the synthesis of C-disaccharides and differently protected C-aryl glycosides. Carbohydrate Research, 468, 64-68. https://doi.org/10.1016/j.carres.2018.08.013
Dubbu S, et al. Stereoselective Synthesis of 2-deoxy-β-C-aryl/alkyl Glycosides Using Prins Cyclization: Application in the Synthesis of C-disaccharides and Differently Protected C-aryl Glycosides. Carbohydr Res. 2018;468:64-68. PubMed PMID: 30153553.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Stereoselective synthesis of 2-deoxy-β-C-aryl/alkyl glycosides using Prins cyclization: Application in the synthesis of C-disaccharides and differently protected C-aryl glycosides. AU - Dubbu,Sateesh, AU - Chennaiah,Ande, AU - Verma,Ashish Kumar, AU - Vankar,Yashwant D, Y1 - 2018/08/22/ PY - 2018/07/26/received PY - 2018/08/20/revised PY - 2018/08/20/accepted PY - 2018/8/29/pubmed PY - 2018/11/6/medline PY - 2018/8/29/entrez KW - C-Aryl/alkyl glycosides KW - Carbohydrates KW - D-mannitol KW - Glycosylation KW - Prins reaction SP - 64 EP - 68 JF - Carbohydrate research JO - Carbohydr. Res. VL - 468 N2 - 2-Deoxy-β-C-aryl/alkyl glycosides were synthesized from di-O-pivaloyl protected homoallylic alcohol derived from D-mannitol with various aldehydes via the Prins cyclization. The salient features of this methodology are high yields and excellent stereoselectivity. This method has also been successfully applied to the synthesis of differently protected 2-deoxy-β-C-aryl glycosides and C-disaccharides. One of the 2-deoxy-β-C-aryl glycosides was utilized as a glycosyl acceptor in the glycosylation to synthesize an O-linked disaccharides. SN - 1873-426X UR - https://www.unboundmedicine.com/medline/citation/30153553/Stereoselective_synthesis_of_2_deoxy_β_C_aryl/alkyl_glycosides_using_Prins_cyclization:_Application_in_the_synthesis_of_C_disaccharides_and_differently_protected_C_aryl_glycosides_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0008-6215(18)30443-9 DB - PRIME DP - Unbound Medicine ER -