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Volumn 119, Issue 24, 1997, Pages 5562-5566

Intramolecular aglycon delivery on polymer support: Gatekeeper monitored glycosylation

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; DISACCHARIDE; FLUORIDE; GLYCOSIDE; MANNOSIDE; OLIGOSACCHARIDE; POLYMER; TRISACCHARIDE;

EID: 0030791784     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja964093p     Document Type: Article
Times cited : (138)

References (37)
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    • 1H-NMR analysis in the presence of p-nitrobenzaldehyde as an internal standard. For details see Experimental Section
    • 1H-NMR analysis in the presence of p-nitrobenzaldehyde as an internal standard. For details see Experimental Section.
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    • note
    • 1H-NMR analysis of 12a and 12c revealed mixed acetal formation seems to be highly stereoselective, and only a single isomer was detectable. In analogy with nonpolymeric acetals derived from PMB derivatives, the configuration of the acetalic carbon was assigned to be S. (equation presented) Unusually low field shifting of H-1 signal (δ 5.58 for 12a and δ 5.63 for 12c) is characteristic of S isomers (Lergenmüller, M; Nukada, T. Kuramochi, K; Dan, A.; Ito, Y.; Ogawa, T. Unpublished data). Stereochemical considerations of mixed acetal formation will be reported in due course.
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    • Nearly theoretical amount of excess 10a could be recovered from the filtrate
    • Nearly theoretical amount of excess 10a could be recovered from the filtrate.
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    • The reaction proceeds in a nearly identical efficiency in the absence of MeSSMe (entry 2). Careful inspection of TLC revealed the minor formation of 8a which was isolated in ca. 5% yield. This phenomenon might be due to partial cleavage of the acetal linkage under the reaction conditions
    • The reaction proceeds in a nearly identical efficiency in the absence of MeSSMe (entry 2). Careful inspection of TLC revealed the minor formation of 8a which was isolated in ca. 5% yield. This phenomenon might be due to partial cleavage of the acetal linkage under the reaction conditions.
  • 33
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    • 1H-NMR (see Supporting Information)
    • 1H-NMR (see Supporting Information).


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