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Additive-Free Gold(III)-Catalyzed Stereoselective Synthesis of 2-Deoxyglycosides Using Phenylpropiolate Glycosides as Donors.
Chem Asian J. 2019 Dec 13; 14(24):4651-4658.CA

Abstract

Stereoselective synthesis of deoxyglycosides has been achieved from benchtop stable and easily synthesizable deoxy-phenylpropiolate glycosides (D-PPGs) using gold(III) salt as catalyst under external additive-free conditions. Under a simple catalytic system, D-PPGs reacted with a variety of sugar and non-sugar acceptors to produce majorly α-stereoselective O/N-deoxyglycosides in good to excellent yields and regenerate easily separable and reusable phenylpropiolic acid. Deoxy-PPGs containing armed and disarmed groups survived well under the optimized reaction conditions. In addition, the orthogonal nature of D-PPGs was showcased, and 1,1'-linked trehalose-type sugar was also synthesized.

Authors+Show Affiliations

Department of Chemistry, Indian Institute of Technology Patna, Bihta, 801106, Bihar, India.Department of Chemistry, Indian Institute of Technology Patna, Bihta, 801106, Bihar, India.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

31381256

Citation

Shaw, Mukta, and Amit Kumar. "Additive-Free Gold(III)-Catalyzed Stereoselective Synthesis of 2-Deoxyglycosides Using Phenylpropiolate Glycosides as Donors." Chemistry, an Asian Journal, vol. 14, no. 24, 2019, pp. 4651-4658.
Shaw M, Kumar A. Additive-Free Gold(III)-Catalyzed Stereoselective Synthesis of 2-Deoxyglycosides Using Phenylpropiolate Glycosides as Donors. Chem Asian J. 2019;14(24):4651-4658.
Shaw, M., & Kumar, A. (2019). Additive-Free Gold(III)-Catalyzed Stereoselective Synthesis of 2-Deoxyglycosides Using Phenylpropiolate Glycosides as Donors. Chemistry, an Asian Journal, 14(24), 4651-4658. https://doi.org/10.1002/asia.201900888
Shaw M, Kumar A. Additive-Free Gold(III)-Catalyzed Stereoselective Synthesis of 2-Deoxyglycosides Using Phenylpropiolate Glycosides as Donors. Chem Asian J. 2019 Dec 13;14(24):4651-4658. PubMed PMID: 31381256.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Additive-Free Gold(III)-Catalyzed Stereoselective Synthesis of 2-Deoxyglycosides Using Phenylpropiolate Glycosides as Donors. AU - Shaw,Mukta, AU - Kumar,Amit, Y1 - 2019/08/13/ PY - 2019/07/01/received PY - 2019/08/05/revised PY - 2019/8/6/pubmed PY - 2019/8/6/medline PY - 2019/8/6/entrez KW - bifunctional donors KW - deoxy-phenylpropiolate KW - reusable and recyclable leaving group KW - stereoselective glycosylation SP - 4651 EP - 4658 JF - Chemistry, an Asian journal JO - Chem Asian J VL - 14 IS - 24 N2 - Stereoselective synthesis of deoxyglycosides has been achieved from benchtop stable and easily synthesizable deoxy-phenylpropiolate glycosides (D-PPGs) using gold(III) salt as catalyst under external additive-free conditions. Under a simple catalytic system, D-PPGs reacted with a variety of sugar and non-sugar acceptors to produce majorly α-stereoselective O/N-deoxyglycosides in good to excellent yields and regenerate easily separable and reusable phenylpropiolic acid. Deoxy-PPGs containing armed and disarmed groups survived well under the optimized reaction conditions. In addition, the orthogonal nature of D-PPGs was showcased, and 1,1'-linked trehalose-type sugar was also synthesized. SN - 1861-471X UR - https://www.unboundmedicine.com/medline/citation/31381256/Additive_Free_Gold_III__Catalyzed_Stereoselective_Synthesis_of_2_Deoxyglycosides_Using_Phenylpropiolate_Glycosides_as_Donors_ L2 - https://doi.org/10.1002/asia.201900888 DB - PRIME DP - Unbound Medicine ER -
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