2-乙酰氨基-2-去氧-3,6-二-氧-苄基-α-D-吡喃葡萄糖烯丙基苷的合成工艺优化
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摘要
以N-乙酰氨基葡萄糖为原料,经烯丙基化、苯亚甲基化、苄基化和选择性开环等4步反应,合成了2-乙酰氨基-2-去氧-3,6-二-氧-苄基-α-D-吡喃葡萄糖烯丙基苷,总收率53.4%,其结构经~1H NMR,~(13)C NMR和LC-MS(ESI)确证。
Allyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-α-D-glucopyranoside was synthesized from N-acetyl-D-glucosamine via a four-step reaction of allylation, benzylidenation, benzylation and selective ring opening reaction with an overall yield of 53.4%. The structure of was confirmed by ~1H NMR, ~(13)C NMR and LC-MS(ESI).
Allyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-α-D-glucopyranoside was synthesized from N-acetyl-D-glucosamine via a four-step reaction of allylation, benzylidenation, benzylation and selective ring opening reaction with an overall yield of 53.4%. The structure of was confirmed by ~1H NMR, ~(13)C NMR and LC-MS(ESI).
引文
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[2] CUI Y Q, SHEN R W. Effect of N-acetyl gucosamine on osteoblastic actitvity and expression bone morphogenetic protein in fracture healing[J].Chin J Clin Rehabilit,2006,10(5):158-160.
[3] 李慧,曹秀明,季宇彬,等. N-乙酰氨基葡萄糖及D-氨基葡萄糖盐酸盐研究进展[J].黑龙江医药,2007,20(2):110-120.
[4] WU T J, ZHOU H P, JIN Z X, et al. Cardio protection of salidroside from ischemia/reperfusion injury by increasing N-acetyl glucosamine linkage to cellular proteins[J].Eur J Pharmacol,2009,613(1-3):93-99.
[5] BUTKINAREE C, PARK K, HART G W. O-linked β-N-acetyl glucosamine(O-GlcNAc):Extensive crosstalk with phosphorylation to regulate signaling and transcription in response to nutrients and stress[J].Biochimi Biophysi Acta(BBA)-General Subjects,2010,1800(2):96-106.
[6] 赵莹,吴小兰,刘俊康,等. N-乙酰氨基葡萄糖对乙醇致肝组织损伤的保护作用及其机制[J].吉林大学学报(医学版),2011,37(03):456-459.
[7] CHEN Y S, ADEYEYE J, BYSTRICKY P, et al. The capsule polysaccharide structure and biogenesis for non-O1 vibrio cholerae NRT36S:Genes are embedded in the LPS region[J].BMC Microbiol,2007,7:20-22.
[8] TOWNSENDR R, LEE Y C, WONG T C, et al. Binding of N-linked bovine fetuin glycopeptides to isolated rabbit hepatocytes:Gal/GalNAc Hepatic lectin discrimination between Gal/β(l,4) GlcNAc and Galβ(l,3) GlcNAc in a triantennary structure1[J].Biochemistry,1986,25:5716-5725.
[9] SUZUKI N, YAMAMOTO K. Molecular cloning of pigeon UDP-galactose:β-D-Galactoside α 1,4-Galactosyltransferase and UDP-galactose:β-D-Galactoside β 1,4-Galact-osyltransferase,two novel enzymes catalyzing the formation of Galα1-4Galβ1-4Galβ1-4GlcN-Ac sequence[J].Bio Chem,2010,285(8):5178-5187.
[10] FENG F, OKUYAMA K, NISHIMURA S I, et al. Chemo-enzymatic synthesis of fluorinated 2-N- acetamidosugar nucleotides using UDP-GlcNAc pyrophosphorylase[J].Org Biomol Chem,2004,2:1617-1623.
[11] NIETOP M, AUGULO J, REICHARDT N, et al. Effect of the substituents of the neighboring ring in the conformational equilibrium of iduronate in heparin-like trisaccharides[J].Chem Eur J,2012,18:16319-16331.