129519-27-3Relevant articles and documents
New monosaccharide derivatives and biological applications thereof
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Paragraph 0045, (2014/01/07)
The invention relates to monosaccharide derivatives of formula (I) wherein the dotted line represents a possible second bond, X is CH2, CHF, CF2, CHOH, O, S or NH, Y is P(O) (ORa) (ORb) or P(O) (ORa) (NRaRb), A1 is O, S, NRa, N(CO)Ra, N(SO)Ra or N(SO2)Ra, A2 and A3 are H, F, NRcRd, NRc(CO)Rd, NRc(SO)Rd, NRc(SO2)Rd and ORc and A2 may also be an oxime NORc, A4 is H, F or OH, W1 and W2 are as defined in the application, as are Ra, Rb, Rc and Rd, and their addition salts thereof with acids and bases, their preparation and their use in the antibacterial prevention and therapy, used alone or in association with antibacterials, antivirulence agents or drugs reinforcing the host innate immunity, and pharmaceutical compositions and associations containing them.
NEW MONOSACCHARIDE DERIVATIVES AND BIOLOGICAL APPLICATIONS THEREOF
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Page/Page column 20; 21, (2014/01/07)
The invention relates to monosaccharide derivatives formula (I) wherein the dotted line represents a possible second bond, X is CH2, CHF, CF2, CHOH, O, S or NH, Y is P (O) (ORa) (ORb) or P (O) (ORa) (NRaRb), A1 is O, S, NRa, N(CO)Ra, N(SO)Ra or N(SO2)Ra, A2 and A3 are H, F, NRcRd, NRc(CO)Rd, NRc(SO)Rd, NRc(SO2)Rd and ORC and A2 may also be an oxime NORc, A4 is H, F or OH, W1 and W2 are as defined in the application, as are Ra, Rb, Rc and Rd, and their addition salts thereof with acids and bases, their preparation and their use in the antibacterial prevention and therapy, used alone or in association with antibacterials, antivirulence agents or drugs reinforcing the host innate immunity, and pharmaceutical compositions and associations containing them.
Efficient synthesis of lactosaminylated core-2 O-glycans
Misra, Anup Kumar,Fukuda, Minoru,Hindsgaul, Ole
, p. 2667 - 2669 (2007/10/03)
A series of lactosaminylated oligosaccharides found in mucin type O-glycans was synthesized using a generalized block strategy. The synthesis involved the addition of a protected lactosamine donor to a partially protected T-disaccharide derivative. The nonreducing galactose residues of the deblocked oligosaccharide products could be removed by β-galactosidase from jack bean to produce the corresponding GlcNAc terminated compounds. A series of tri- to hexasaccharides was thus efficiently produced.
Synthesis of a fully protected glycooctaosyl serine isolated from blood group A human ovarian mucin
Macindoe,Nakahara,Ogawa
, p. 207 - 216 (2007/10/02)
N-(9-Fluorenylmethoxycarbonyl)-O-{[O-(2-acetamido-3,4,6-tri-O-acetyl- 2-deoxy-α-D-galactopyranosyl)-(1 → 3)-O-[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1 → 2)]-O-(4,6-di-O-acetyl-β-D-galactopyranosyl)-(1 → 3)-O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-gl
Synthesis of a selectively protected trisaccharide building block that is part of xylose-containing carbohydrate chains from N-glycoproteins
Kerekgyarto, Janos,Ven, Jos G. M. van der,Kamerling, Johannis P.,Liptak, Andras,Vliegenthart, Johannes F. G.
, p. 135 - 146 (2007/10/02)
The synthesis is reported of ethyl 4-O--3,6-di-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (16), a key intermediate in the synthesis of xylose-cont
Synthesis of N-Acetylallosamine-Derived Disaccharides
Maloisel, Jean-Luc,Vasella, Andrea
, p. 1491 - 1514 (2007/10/02)
The protected disaccharide 44, a precursor for the synthesis of allosamidin, was prepared from the glycosyl acceptor 8 and the donors 26-28, best yields being obtained with the trichloroacetimidate 28 (Scheme 6).Glycosidation of 8 or of 32 by the triacetylated, less reactive donors 38-40 gave the disaccharides 46 and 45, respectively, in lower yields (Scheme 7).Regioselective glycosidation of the diol 35 by the donors 38-40 gave 42, the axial, intramolecularly H-bonded OH-C(3) group reacting exclusively (Schmeme 5).The glycosyl acceptor 8 was prepared from 9 by reductive opening of the dioxolane ring (Scheme 3).The donors 26-28 were prepared from the same precursor 9 via the hemiacetal 25.To obtain 9, the known 10 was de-N-acetylated (-> 18), treated with phthalic anhydride (-> 19), and benzylated, leading to 9 and 23 (Schemes 2 and 3).Saponification of 23, followed by acetylation also gave 9.Depending upon the conditions, acetylation of 19 yielded a mixture of 20 and 21 or exclusively 20.Deacetylation of 20 led to the hydroxyphthalimide 22.De-N-acetylation of the 3-O-benzylated α-D-glycosides 11 and 15, which were both obtained from 10, was very sluggish and accompanied by partial reduction of the O-allyl to an O-propyl group (Scheme 2).The β-D-glycoside 30 behaved very similarly to 11 and 15.Reductive ring opening of 31, derived from 29, yielded the 3-O-acetylated acceptor 32, while the analogous reaction of the α-D-anomer 20 was accompanied by a rapid 3-O -> 4-O acyl migration (-> 34; Scheme 4).Reductive ring opening of 21 gave the diol 35.The triacetylated donors 38-40 were obtained from 20 by debenzylidenation, acetylation (-> 36), and deallylation (-> 37), followed by either acetylation (-> 38), treatment with Me3SiSEt (-> 39), or Cl3CCN (-> 40).
Synthesis of β-D-mannosides from β-D-glucosides via an intramolecular SN2 reaction at C-2
Gunther,Kunz
, p. 217 - 241 (2007/10/02)
The selective synthesis of β-D-mannosides was achieved by first synthesizing β-D-glucosides that carry an N-phenylcarbamoyl protecting group at O-3. These derivatives were transformed into the corresponding β-D-mannosides by intramolecular nucleophilic su
