Mechanistic studies on the stereoselective formation of glycosyl iodides: first characterization of ¢l-D-glycosyl iodides (Record no. 45973)

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control field MX-MdCICY
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control field 20250625140656.0
040 ## - CATALOGING SOURCE
Transcribing agency CICY
090 ## - LOCALLY ASSIGNED LC-TYPE CALL NUMBER (OCLC); LOCAL CALL NUMBER (RLIN)
Classification number (OCLC) (R) ; Classification number, CALL (RLIN) (NR) B-11757
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Title Mechanistic studies on the stereoselective formation of glycosyl iodides: first characterization of ¢l-D-glycosyl iodides
490 0# - SERIES STATEMENT
Volume/sequential designation Carbohydrate Research, 300(2), p.119-125, 1997
520 3# - SUMMARY, ETC.
Summary, etc. Treatment of glycosyl acetates with one equivalent of iodotrimethylsilane at low temperature results in the quantitative formation of glycosyl iodides. Carbohydrates that possess a participating group at the C-2 position initially form /3-o-glycosyl iodides, which quickly equilibrate to the o~-iodo anomers. The /3 anomer of peracetylated glucose reacts faster than the ce anomer, presumably because the C-2 acetate can assist in displacing the silylated anomeric acetate. In contrast, the o~ anomer reacts faster than the /3 anomer in substrates lacking a participating group at C-2. For example, activation of 1-O-acetyl-2,3,4,6-tetra-Obenzyl-o~-D-glucopyranose leads to formation of the /3 iodide, while the corresponding /3 acetate produces the ce iodide. Although the /3 iodides quickly equilibrate to the o~ anomers, they can be prepared in sizable quantities at low temperatures where equilibration is slow. This report describes the first stereoselective formation and characterization of /3-D-glycosyl iodides.
650 14 - SUBJECT ADDED ENTRY--TOPICAL TERM
Topical term or geographic name entry element GLYCOSYL IODIDES
650 14 - SUBJECT ADDED ENTRY--TOPICAL TERM
Topical term or geographic name entry element BETA-D-GLYCOSYL IODIDES
650 14 - SUBJECT ADDED ENTRY--TOPICAL TERM
Topical term or geographic name entry element NMR CHARACTERIZATION
700 12 - ADDED ENTRY--PERSONAL NAME
Personal name Gervay, J.
700 12 - ADDED ENTRY--PERSONAL NAME
Personal name Nguyen, T.N.
700 12 - ADDED ENTRY--PERSONAL NAME
Personal name Hadd, M.J.
856 40 - ELECTRONIC LOCATION AND ACCESS
Uniform Resource Identifier <a href="https://drive.google.com/file/d/1l0Z2Pnyh3PspuRw1zOg99as0ng-c47Ua/view?usp=drivesdk">https://drive.google.com/file/d/1l0Z2Pnyh3PspuRw1zOg99as0ng-c47Ua/view?usp=drivesdk</a>
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Source of classification or shelving scheme Clasificación local
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  Clasificación local     Ref1 CICY CICY Documento préstamo interbibliotecario 25.06.2025   B-11757 25.06.2025 25.06.2025 Documentos solicitados