| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1344503 | Tetrahedron: Asymmetry | 2011 | 7 Pages |
The synthesis of four deuterated sialic acids and their 1,7-lactones has been performed in two ways, one based on sialic acid classical chemistry, and the other involving a direct exchange of the unlabeled acyl group of N-acetylneuraminic acid with a labeled one mediated by a perfluorinated amide. The final lactonization is promoted by benzyloxycarbonyl chloride.
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(2R,4S,5R,6R,7S,8R)-2-Benzyloxycarbonyl-β-N-[2H3]-acetyl-neuraminic acid 1,7-lactoneC19H20D3NO10[α]D25=+16.5 (c 1, CH3OH)Source of chirality: natural sialic acidAbsolute configuration: (2R,4S,5R,6R,7S,8R)
(2R,4S,5R,6R,7S,8R)-2-Benzyloxycarbonyl-N-[2H3]-acetyl-β-[3,3-2H2]-neuraminic acid 1,7-lactoneC19H18D5NO10[α]D25=+17.2 (c 1, CH3OH)Source of chirality: natural sialic acidAbsolute configuration: (2R,4S,5R,6R,7S,8R)
(2R,4S,5R,6R,7S,8R)-2-Benzyloxycarbonyl-N-[2H2]-glycolyl-β-neuraminic acid 1,7-lactoneC19H21D2NO11[α]D25=+9.0 (c 1, CH3OH)Source of chirality: natural sialic acidAbsolute configuration: (2R,4S,5R,6R,7S,8R)
(2R,4S,5R,6R,7S,8R)-2-Benzyloxycarbonyl-N-[2H2]-glycolyl-β-[3,3-2H2]-neuraminic acid 1,7-lactoneC19H19D4NO11[α]D25=+9.3 (c 1, CH3OH)Source of chirality: natural sialic acidAbsolute configuration: (2R,4S,5R,6R,7S,8R)
(2R,4S,5R,6R,7S,8R)-N-[2H3]-acetyl-β-neuraminic acid 1,7-lactoneC11H14D3NO8[α]D25=+25.0 (c 1, THF)Source of chirality: natural sialic acidAbsolute configuration: (2R,4S,5R,6R,7S,8R)
(2R,4S,5R,6R,7S,8R)-N-[2H3]-acetyl-β-[3,3-2H2]-β-neuraminic acid 1,7-lactoneC11H12D5NO8[α]D25=+27.0 (c 1, THF)Source of chirality: natural sialic acidAbsolute configuration: (2R,4S,5R,6R,7S,8R)
(2R,4S,5R,6R,7S,8R)-2-N-[2H2]-glycolyl-β-neuraminic acid 1,7-lactoneC11H15D2NO9[α]D25=+9.0 (c 1, THF)Source of chirality: natural sialic acidAbsolute configuration: (2R,4S,5R,6R,7S,8R)
(2R,4S,5R,6R,7S,8R)-N-[2H2]-glycolyl-β-[3,3-2H2]-neuraminic acid 1,7-lactoneC19H19D4NO11[α]D25=+9.3 (c 1, CH3OH)Source of chirality: natural sialic acidAbsolute configuration: (2R,4S,5R,6R,7S,8R)
(2R,4S,5R,6R,7S,8R)-N-[2H3]-acetyl-2-O-methyl ester-β-neuraminic acid methyl esterC13H20D3NO9[α]D25=-7.5 (c 1, CHCl3)Source of chirality: natural sialic acidAbsolute configuration: (2R,4S,5R,6R,7S,8R)
(2R,4S,5R,6R,7S,8R)-N-benzyloxy-[2H2]-acetyl-2-O-metyl-β-neuraminic acid methyl esterC20H27D2NO10[α]D25=-35.2 (c 1, H2O)Source of chirality: natural sialic acidAbsolute configuration: (2R,4S,5R,6R,7S,8R)
(2R,4S,5R,6R,7S,8R)-N-[2H2]-Glycolyl-2-O-metyl-β-neuraminic acid methyl esterC13H21D2NO10[α]D25=+7.1 (c 1, CH3OH)Source of chirality: natural sialic acidAbsolute configuration: (2R,4S,5R,6R,7S,8R)
(2R,4S,5R,6R,7S,8R)-N-[2H3]-Acetyl-neuraminic acidC11H16D3NO9[α]D25=-34.0 (c 1, H2O)Source of chirality: natural sialic acidAbsolute configuration: (2R,4S,5R,6R,7S,8R)
(2R,4S,5R,6R,7S,8R)-N-[2H3]-Acetyl-[3,3-2H2]-neuraminic acidC11H14D5NO9[α]D25=-33.2 (c 1, H2O)Source of chirality: natural sialic acidAbsolute configuration: (2R,4S,5R,6R,7S,8R)
(2R,4S,5R,6R,7S,8R)-N-[2H2]-Glycoyl-neuraminic acidC11H17D2NO10[α]D25=-36.1 (c 1, H2O)Source of chirality: natural sialic acidAbsolute configuration: (2R,4S,5R,6R,7S,8R)
(2R,4S,5R,6R,7S,8R)-N-[2H2]-Glycoyl-[3,3-2H2]-neuraminic acidC11H15D4NO10[α]D25=-35.0 (c 1, H2O)Source of chirality: natural sialic acidAbsolute configuration: (2R,4S,5R,6R,7S,8R)
(2R,4S,5R,6R,7S,8R)-2,4,7,8,9-Penta-O-acetyl-5-N-[2H3]-acetyl-β-neuraminic acid methyl esterC22H28D3NO14[α]D25=-18.3 (c 1, CHCl3)Source of chirality: natural sialic acidAbsolute configuration: (2R,4S,5R,6R,7S,8R)
(2R,4S,5R,6R,7S,8R)-2,4,7,8,9-Penta-O-acetyl-5-N-benzyloxy-[2H2]-acetyl-β-neuraminic acid methyl esterC29H35D2NO15[α]D25=-9.3 (c 1, CHCl3)Source of chirality: natural sialic acidAbsolute configuration: (2R,4S,5R,6R,7S,8R)
