Synthesis of the first deprotected indigo N-glycosides (blue sugars) by reductive glycosylation of dehydroindigo

Tetrahedron Letters

Volumn 47, Issue 32, 2006, Pages 5741-5745

  Hein, Martin ^a   Phuong, Nguyen Thi Bich ^a,b   Michalik, Dirk ^c   Görls, Helmar ^d   Lalk, Michael ^b   Langer, Peter ^a,c  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b UNIVERSITY OF GREIFSWALD   (Germany)

^c LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

^d FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

Dehydroindigo; Indigo; N Heterocycles; Regioselectivity

Indexed keywords

CARBOHYDRATE DERIVATIVE; GLUCOSE DERIVATIVE; GLYCOSIDE; IODINE DERIVATIVE; MANNOSE; RHAMNOSE;

ARTICLE; DEPROTECTION REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; GLYCOSYLATION; REDUCTION;

EID: 33745923540     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.06.021     Document Type: Article

References (15)

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12. 2 (800 mg, 10.25 mmol) and the reaction mixture was stirred at 70 °C until one main spot of blue colour could be detected by TLC (2-3 h). The pyridine and acetic anhydride were removed by distillation under reduced pressure and the residue was purified by column chromatography (EtOAc/toluene = 1:5 → 1:2) to give 5 (198 mg, 22%, α/β = 2:1) as a blue solid. An analytically pure sample of the α anomer was isolated by repeated crystallisation from methanol.
13. 13C NMR (125.8 MHz, DMSO) δ: 188.4 (C-3); 187.1 (C-10); 152.1 (C-14a); 151.9 (C-7a); 136.5 (C-13); 134.5 (C-6); 125.1 (C-9); 124.3 (C-11); 123.1 (C-2); 122.3 (C-4); 121.4 (C-3a); 121.1 (C-5); 120.6 (C-12); 119.9 (C-7); 119.3 (C-10a); 113.3 (C-14); 88.1 (C-15); 75.3 (C-19); 73.4 (C-17); 72.8 (C-16); 71.9 (C-18); 18.3 (C-20).{A figure is presented}
14. CCDC-293346 contains all crystallographic details of this publication and is available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, GB-Cambridge CB21EZ; Fax: +44 1223 336 033; or deposit@ccdc.cam.ac.uk.
15. +): 592.1688; found: 592.1682.{A figure is presented}