All Library Books, journals and Electronic Records Telegrafenberg

feed icon rss

Your email was sent successfully. Check your inbox.

An error occurred while sending the email. Please try again.

Proceed reservation?

Proceed order?

  • 1
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1994 (1994), S. 659-664 
    ISSN: 0170-2041
    Keywords: Glycosylations ; Protecting groups ; Benzoyl, 2-chloroacetoxymethyl- ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The application of the 2-(chloroacetoxymethyl)benzoyl (CAMB) group to the O-protection of position 2 in glycosyl donors is described. Saponification of the phthalide and subsequent chloroacetylation of 2-(hydroxymethyl)benzoic acid (1) gave 2-(chloroacetoxymethyl)benzoic acid (2). Treatment of 2 with thionyl chloride afforded the acyl chloride 3. Acylation of O-2 of 1,3,4,6-tetra-O-acetyl-α-D-glucopyranose (4a), galactopyranose (4b) and of the amino group of 1,3,4,6-tetra-O-acetyl-2-amino-2-deoxy-β-D-glucopyranose (4c) afforded the fully protected pyranose derivatives 5a-c in high yields. Compounds 5a and 5b were converted with HBr in acetic acid into the corresponding 2-O-CAMB-protected bromides 6a, b in excellent yields. Silver trifluoromethanesulfonate promoted glycosylation of the latter with 2-hydroxyethyl benzoate yielded the β-glycosides 8a (74%) and 8b (69%). Direct activation of the glucosamine derivative 5c with ferric chloride gave the glucoside 8c (54%). Furthermore, the galactosyl bromide 6b was coupled with methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside (11) affording the 2′-O-CAMB-protected methyl glycoside disaccharide 12 (63%). Similarly, condensation of the glucosyl bromide 6a with 4a gave the β-(1→2)-linked disaccharide 13 (45%). Treatment of compounds 8a and 13 with thiourea resulted in the deblocked glycosides 9a and 14. Similar deprotection of 8b gave 2-benzoyloxyethyl 3,4,6-tri-O-acetyl-β-D-galactopyranoside (9b) and the 2-O-[2-(hydroxymethyl)benzoyl] derivative 10. Reaction of 8c with thiourea afforded solely the dechloroacetylated glucoside 9c.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    Location Call Number Expected Availability
    BibTip Others were also interested in ...
  • 2
    Publication Date: 1995-08-01
    Print ISSN: 0040-4039
    Electronic ISSN: 1873-3581
    Topics: Chemistry and Pharmacology
    Published by Elsevier
    Location Call Number Expected Availability
    BibTip Others were also interested in ...
Close ⊗
This website uses cookies and the analysis tool Matomo. More information can be found here...