- Synthesis of sphingadienine-type glucocerebrosides
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Sphinga-4,8-dienine derivatives were synthesized from a vinyl-epoxide 5 via three routes. First, reaction of 5 with 2-dodecenyl cyanocuprate afforded a 1:1 mixture of (4E,8E)- and (4E,8Z)-sphingadienine derivatives in high yield. Second, the (4E,8E)-isome
- Murakami, Teiichi,Shimizu, Toshimi,Taguchi, Kazuhiro
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p. 533 - 545
(2007/10/03)
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- Glycosyl Imidates, 35. - Synthesis of a Cerebroside Having a (4E,8E)-Sphingadienine Moiety from Tetragonia tetragonoides with Antiulcerogenic Activity
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The natural cerebroside 1a possessing antiulcerogenig activity and its diastereomer 1b were readily synthesized by the azidosphingosine glycosylation method.The requied (4E,8E)-azidosphingadienine 12 was obtained from (4E)-tetradecenyl bromide (7) and 2,4-O-benzylidene-D-threose (9) by Wittig reaction, subsequent azide introduction and benzylidene group removal.For the glucosylation the corresponding 3-O-benzoyl derivative 15 was prepared; it provided with the trichloroacetimidate 16 as glucosyl donor the desired β-D-glucopyranosyl derivative 17 in high yield.Deprotection and azido group reduction afforded compound 19 with a free amino group.N-Acylation with both enantiomers of 2-hydroxypalmitic acid (using the derivatives 20 a,b) yielded after deacetylation compounds 1a and 1b, respectively.
- Baer, Thomas,Schmidt, Richard R.
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p. 669 - 674
(2007/10/02)
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- Synthesis of Sphingosine Relatives, VII. - Synthesis fo Anti-Ulcerogenic Cerebrosides Isolated from Tetragonia tetragonoides
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The synthesis of (2S,3R,4E,8E,2'R)-1-O-(β-D-glucopyranosyl)-N-(2'-hydroxyhexadecanoyl)-4,8-sphingadienine (1a) and its (8Z) isomer (1b) was accomplished by employing (R)-2-aminohexadecanoic acid, D-glucose, and (S)-serine as chiral sources.
- Mori, Kenji,Kinsho, Takeshi
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p. 807 - 814
(2007/10/02)
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