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Volumn 6, Issue 1, 2000, Pages 172-186

1,2-Diacetals in synthesis: Total synthesis of a glycosylphosphatidylinositol anchor of Trypanosoma brucei

Author keywords

1,2 diacetals; Glycosylations; GPI anchors; Inositols; Oligosaccharides

Indexed keywords

ACETAL DERIVATIVE; BUTANE; GLUCOSAMINE; GLYCOSYLPHOSPHATIDYLINOSITOL; GLYPICAN; INOSITOL; INOSITOL DERIVATIVE; OLIGOSACCHARIDE; SELENIUM; THIOGLYCOSIDE;

EID: 0033985424     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(20000103)6:1<172::aid-chem172>3.3.co;2-x     Document Type: Article
Times cited : (93)

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    • note
    • The structure of side product 12 was determined by x-ray crystallography after benzylation of the hydroxyl group.
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    • note
    • -1.
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    • note
    • The analogous thiophenyl compound 29 was chosen for the large scale synthesis of bromide 33 as a result of the higher crystallinity of the intermediates and over 10 mmol of 29 was prepared under the same reaction conditions and in comparable yields.
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    • note
    • Minor amounts of the undesired β-isomer were readily separated at this stage.
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    • note
    • 9 and 46 were always freshly prepared because migration of the chloroacetate to the 3-hydroxyl was observed upon prolonged standing even at -20°C.
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    • note
    • The corresponding fluoride was also prepared and shown to be too unreactive for synthetic use.
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    • note
    • It should be noted that TPS deprotection of 47 with HF · pyridine was slow and low yielding while TBAF treatment led to removal of the chloroacetate groups.
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    • note
    • 3 solutions should therefore never be evaporated to dryness!


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.