3-oxa-5-chloropentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside | 212896-41-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-oxa-5-chloropentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: 5-chloro-3-oxapentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• CAS: 212896-41-8
• 化学式: C₁₈H₂₈ClNO₁₀
• 分子量: 453.874
• InChiKey: SLHJZADCDQQWCG-DUQPFJRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.09
• 重原子数：
  30.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  135.69
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3-oxa-5-chloropentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-chloro-3-oxapentyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Chemoenzymatic synthesis of spacer-linked oligosaccharides for the preparation of neoglycoproteins

  摘要：

  In the present work, the combination of chemical and enzymatic methods to obtain neoglycoproteins is described. Three bovine serum albumin (BSA)-conjugates, BSA-[GalNAc alpha-], BSA-[Gal(beta 1-3)GalNAc(alpha-], and BSA-[Neu5Ac(alpha 2-3)Gal(beta 1-3)GalNAc(alpha-], were prepared, alpha GalNAc derivatives were galactosylated employing crude P-galactosidase from bovine testes. The use of oversaturated donor solutions (pNP beta Gal) enhanced the yields up to 60%. This method was verified using divalent structures as accepters, that rendered di- and tri-galactosylated products. Further treatment of the disaccharides with CMP-Neu5Ac and alpha 2-3 sialyltransferase from pork liver led to formation of trisaccharides. Finally, mono-, di-, and trisaccharides were coupled to BSA employing a thiolic group introduced into the protein for Michael addition to a maleinimide group in the spacer-ann of the saccharide components. The results were monitored by HPLC and MALDI-TOF. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00073-7
• 作为产物：
  描述：

  2-氯乙氧基乙醇 、 2-乙酰氨基-3,4,6-三-O-乙酰-2-脱氧-α-D-吡喃葡萄糖酰基氯 在 3 A molecular sieve 、 mercury(II) iodide 作用下， 以 1,2-二氯乙烷 为溶剂， 以62%的产率得到3-oxa-5-chloropentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis and modification of spacered glycosides of N-acetylglucosamine

  摘要：

  DOI：

  10.1007/bf02254805

文献信息

• Zemlyakov; Kur'yanov; Sidorova, Russian Journal of Bioorganic Chemistry, 1998, vol. 24, # 8, p. 551 - 558
  作者：Zemlyakov、Kur'yanov、Sidorova、Chirva

  DOI：——

  日期：——