Synthetic 6-O-methylglucose-containing polysaccharides (sMGPs): Design and synthesis

Journal of Organic Chemistry

Volumn 72, Issue 6, 2007, Pages 1941-1950

  Meppen, Malte ^a   Wang, Yonghui ^a   Cheon, Hwan Sung ^a   Kishi, Yoshito ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL PROPERTIES; GLYCOSIDATION; GLYCOSYL DONORS; PRECURSORS;

BIOACTIVITY; GLUCOSE; GLYCOSYLATION; OLIGOMERS; SYNTHESIS (CHEMICAL);

POLYSACCHARIDES;

6 O METHYLGLUCOSE CONTAINING POLYSACCHARIDE; ALPHA CYCLODEXTRIN; BETA CYCLODEXTRIN; GAMMA CYCLODEXTRIN; GLUCOSE DERIVATIVE; METHYL GROUP; POLYSACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; GLYCOSIDATION; MUKAIYAMA REACTION; REACTION ANALYSIS; STRUCTURE ANALYSIS;

CYCLODEXTRINS; DRUG DESIGN; GLYCOSYLATION; METHYLGLUCOSIDES; MOLECULAR MIMICRY; OLIGOSACCHARIDES; POLYSACCHARIDES;

EID: 33947227493     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061990v     Document Type: Article

References (47)

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35. 1H NMR and MS (MALDI-TOF) and was further confirmed by transforming them to the known acceptors 9a-c.
36. Following the same sequences as shown in Schemes 6 and 7, β-anomer enriched 9a-c were converted to the β-anomer enriched sMGP 14a-c. For details, see Supporting Information.
37. The profile of Mukaiyama glycosidation in the glucose series was different from that in the mannose series. However, considering the total number of glycosidic bonds present in the product as well as the starting materials, we were concerned with the possibility that the "truncated/ scrambled" products might be contaminated in the products in the gluco series as well. To address this issue, the glycosidation was purposely run for a prolonged time at 0 °C, and the product was subjected to mass spectrometry and size-exclusion chromatography, thereby showing that the product mixture thus obtained was indeed contaminated by a small amount of "truncated" oligomers. Interestingly, these oligomers were formed by cleavage of glycosidic bonds exclusively at the hexoses bearing benzyl protection groups, suggesting that electron-withdrawing groups on C2 hydroxyl groups destabilize carbocation formation and suppress the truncation. When the reaction was carried out at -30 °C, the process forming the truncated oligomers was completely suppressed.
38. 1H NMR analysis, the major byproduct appeared to be a benzyl glycoside of the donors.
39. 1H NMR spectrum was carried out. The absence of the doublet peak (J = 8.0 Hz) at 4.48 ppm demonstrated no contamination with the β-anomer at the newly introduced anomeric center. Similarly, the absence of the doublet (J = 8.0 Hz) at 4.45 ppm demonstrated no contamination with the β-propyl anomer at the reducing end.
40. For details, see Supporting Information.
41. 1H NMR analysis in comparison with the corresponding sMGP 14-mer series.
42. With use of the reported synthetic route, sMGP 6-, 7-, 8-, 10-, 12-, 14-, 16-, 18-, and 20-mers were synthesized. For details, see Supporting Information.
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