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Volumn 46, Issue 30, 2005, Pages 5043-5047

A concise synthesis of (3S,4S,5R)-1-(α-d-galactopyranosyl)-3- tetracosanoylamino-4,5-decanediol, a C-glycoside analogue of immunomodulating α-galactosylceramide OCH

Author keywords

C glycoside; CD1d; Ceramide; NKT cell ligand; OCH

Indexed keywords

1 (ALPHA DEXTRO GALACTOPYRANOSYL) 3 TETRACOSANOYLAMINO 4,5 DECANEDIOL; ALDEHYDE DERIVATIVE; ALPHA GALACTOSYLCERAMIDE; ANTIMALARIAL AGENT; ARABINOSE; CARBOHYDRATE DERIVATIVE; GALACTOSE; GLYCOSIDE; PHYTOSPHINGOSINE; UNCLASSIFIED DRUG;

EID: 20544439073     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.05.069     Document Type: Article
Times cited : (29)

References (36)
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    • 6b and more practical for 2a which completes in only 11 steps, however, it requires the commercially available phytosphingosine and is not expandable enough for analogue syntheses including 2b. Preparing commercially unavailable phytosphingosine derivatives for this route must require several additional steps, which makes this route less attractive for SAR purposes
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    • note
    • In this reaction, the starting α-ethynyl-galactopyranose 5 was usually recovered unchanged in over 15% yield.
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    • 20544449124 scopus 로고    scopus 로고
    • note
    • 3): δ 7.6-7.57 (m, 2H), 7.5-7.2 (m, 23H), 5.66 (dd, 1H, J = 8.9 Hz, 1.8 Hz), 4.90 (d, 1H, J = 11.4 Hz), 4.80 (dd, 1H, J = 6.0 Hz, 1.8 Hz), 4.77 (d, 1H, J = 11.7 Hz), 4.69 (d, 1H, J = 11.7 Hz), 4.68 (d, 1H, J = 11.7 Hz), 4.61 (d, 1H, J = 11.7 Hz), 4.55 (d, 1H, J = 11.4 Hz), 4.45 (d, 1H, J = 11.9 Hz), 4.37 (d, 1H, J = 11.9 Hz), 4.26 (dd, 1H, J = 8.9 Hz, 5.7 Hz), 4.11 (ddd, 1H, J = 13.6 Hz, 5.7 Hz, 3.2 Hz), 4.06 (dd, 1H, J = 9.8 Hz, 5.9 Hz), 3.96 (t, 3H, J = 6.4 Hz), 3.93-3.91 (m, 1H), 3.72 (dd, 1H, J = 9.8 Hz, 2.8 Hz), 3.57 (s, 3H), 3.5-3.4 (m, 2H), 1.75-1.55 (m, 2H), 1.55-1.5 (m, 1H), 1.40 (s, 3H), 1.32 (s, 3H), 1.3-1.1 (m, 5H), 0.81 (t, 3H, J = 6.8 Hz).
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    • note
    • The total chemical yield of 10a,b was decreased to 39% with a similar diastereomeric ratio when the magnesium acetylide of 5 was used in this reaction. The zinc acetylide derived from 5 produced only a trace of 10a,b.
  • 35
    • 20544461858 scopus 로고    scopus 로고
    • note
    • 8, 702.5884, found 702.5853.
  • 36
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    • note
    • The effect of 2b in several animal models of autoimmune disease is currently under investigation and will be reported elsewhere.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.