431981-79-2Relevant academic research and scientific papers
An improved synthetic route to the potent angiogenesis inhibitor benzyl manα(1→3)-Manα(1→3)-Manα(1→3) -Manα(1→2)-Man Hexadecasulfate
Liu, Ligong,Johnstone, Ken D.,Fairweather, Jon K.,Dredge, Keith,Ferro, Vito
experimental part, p. 546 - 552 (2010/01/16)
An improved synthetic route to α(1→3)/α(1→2)-linked mannooligosaccharides has been developed and applied to a more efficient preparation of the potent anti-angiogenic sulfated pentasaccharide, benzyl Manα(1→3)-Manα(1→3)-Manα(1→3) -Manα(1→2)-Man hexadecasu
An efficient and practical synthesis of α-(1→3)-linked mannohexaose and mannooctaose
Chen, Langqiu,Kong, Fanzuo
, p. 341 - 353 (2007/10/03)
α-(1→3)-Linked mannohexaose and mannooctaose as their methyl glycosides were synthesized from condensation of the corresponding α-(1→3)-linked di- (9) and tetrasaccharide donor (21) with the tetrasaccharide acceptor (23), respectively, followed by deacylation. The donor 21 and acceptor 23 were prepared readily from activation of C-1 of the tetrasaccharide 20 and deallylation of the tetrasaccharide 22, respectively. The tetrasaccharide 20 was prepared from oxidative cleavage of 1-O-p-methoxyphenyl of 19, which was obtained from coupling of 9 with 11. The tetrasaccharide 22 was obtained from condensation of the donor 13 with the acceptor 18. These disaccharides 9, 11, 13, and 18 were produced easily by simple chemical transformation using p-methoxyphenyl 3-O-allyl-α-D-mannopyranoside (1) and 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (6), and methyl 3-O-allyl-α-D-mannopyranoside (14) as the synthons.
Synthesis of α-Manp-(1→2)-α-Manp-(1→3)-α-Manp-(1→3)-Manp, the tetrasaccharide repeating unit of Escherichia coli O9a, and α-Manp-(1→2)-α-Manp-(1→2)-α-Manp-(1→3)- α-Manp-(1→3)-Manp, the pentasaccharide repeating unit of E. coli O9 and Klebsiella O3
Chen, Langqiu,Zhu, Yuliang,Kong, Fanzuo
, p. 383 - 390 (2007/10/03)
The tetrasaccharide repeating unit of Escherichia coli O9a, α-D-Manp-(1→2)-α-D-Manp-(1→3)-α-D-Manp- (1→3)-D-Manp, and the pentasaccharide repeating unit of E. coli O9 and Klebsiella O3, α-D-Manp-(1→2)-α-D-Manp-(1→2)-α-D-Manp- (1→3)-α-D-Manp-(1→3)-D-Manp, were synthesized as their methyl glycosides. Thus, selective 3-O-allylation of p-methoxyphenyl α-D-mannopyranoside via a dibutyltin intermediate gave p-methoxyphenyl 3-O-allyl-α-D-mannopyranoside (2) in good yield. Benzoylation (→3), then removal of 1-O-methoxyphenyl (→4), and subsequent trichloroacetimidation afforded the 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroacetimidate (5). Condensation of 5 with methyl 4,6-O-benzylidene-α-D-mannopyranoside (6) selectively afforded the (1→3)-linked disaccharide 7. Benzoylation of 7, debenzylidenation, benzoylation, and deallylation gave methyl 2,4,6-tri-O-benzoyl-α-D-mannopyranosyl-(1→3)-2,4,6-tri-O-benzoyl- α-D-mannopyranoside (11) as the disaccharide acceptor. Coupling of 11 with (1→2)-linked mannose disaccharide donor 17 or trisaccharide donor 21, followed by deacylation, furnished the target tetrasaccharide and pentasaccharide, respectively.
