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- Ellervik, UlfLund University,Lunds universitet,Centrum för analys och syntes,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Centre for Analysis and Synthesis,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH (author)
Synthesis of lactam and acetamido analogues of sialyl Lewis x tetrasaccharide and Lewis x trisaccharide
- Article/chapterEnglish1998
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- 1998-11-24
- American Chemical Society (ACS),1998
- 16 s.
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- LIBRIS-ID:oai:lup.lub.lu.se:1037dd38-9a07-4ffe-abd4-40eeb1f679c4
- https://lup.lub.lu.se/record/1037dd38-9a07-4ffe-abd4-40eeb1f679c4URI
- https://doi.org/10.1021/jo981204pDOI
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- Language:English
- Summary in:English
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- Virtually complete regioselective galactosylation of the diol acceptor p-methoxyphenyl 6-O-benzyl-2-deoxy-2-tetrachlorophthalimido-β-D- glucopyranoside (15) with the donors ethyl 3,4-di-O-acetyl-6-O-benzyl-2- deoxy-2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1-thio-β-D- galactropyranoside (14), 4-methylphenyl 2,3-di-O-acetyl-4-azido-6-O-benzyl- 4-deoxy-1-thio-β-D-galactopyranoside (30), and 4-methylphenyl 2-O-acetyl-4- azido-6-O-benzyl-4-deoxy-3-O-(methoxyethanoyl)-1-thio-β-D-galactopyranoside (44) gave the lactose-diamine derivatives 16, 33, and 45, respectively. Fucosylation of the NHAc derivatives of 16 and 33 (17 and 34) with the donor 18 gave, after deprotection and N-acetylation, the 2-NHAc-Le(x) and 4-NHAc- Le(x) trisaccharides 3 and 5, respectively. Removal of the Troc group from the tetrasaccharide intermediate 23, followed by N-acetylation (→ 24), gave the NHAc-SLe(x) tetrasaccharide 2. Regioselective sialylation of the partially protected trisaccharide diols 21 and 37 with the sialyl donors 22 and 38 gave, after deprotection and lactamization, the SLe(x)-1'''→2'- lactam 1 and the SLe(x)-1'''→4'-lactam 4, respectively. The stannylidene acetal of the trisaccharide diol 21 was regioselectively 3-O-alkylated with tert-butyl bromoacetate; reductive removal of the Troc protecting group and addition of methanolic MeONa caused formation of a lactam ring. Compound 40 was thus obtained over four steps in an overall yield of 52%. Deprotection of 40 furnished the Le(x)-3,2-lactam 6 in 74% yield. Fucosylation of the lactose-diamine derivative 46 with donor 18 gave the N3-Le(x) trisaccharide derivative 47. The azido function of 47 was reduced with H2S, which caused spontaneous closure of a lactam ring. Removal of the protecting groups then gave the Le(x)-3,4-lactam 7. The total yields of 1, 2, 3, 4, 5, and 7 from the monosaccharide starting materials 14, 15, 18, 22, 30, 38, and 44 were 10%, 10%, 22%, 14%, 62%, and 28%, respectively.
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- Grundberg, HansLund University,Lunds universitet(Swepub:lu)ok2-hgr (author)
- Magnusson, GöranLund University,Lunds universitet(Swepub:lu)extLU-74 (author)
- Centrum för analys och syntesKemiska institutionen (creator_code:org_t)
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- In:Journal of Organic Chemistry: American Chemical Society (ACS)63:25, s. 9323-93380022-32631520-6904
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