1-O-Acetyl-2,3,4,6-tetra-O-benzoyl-β-galactofuranose | 89825-84-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-O-Acetyl-2,3,4,6-tetra-O-benzoyl-β-galactofuranose
• 英文别名: 1-O-acetyl-2,3,5,6-tetra-O-benzoyl-β-D-galactose；1-O-acetyl-2,3,5,6-tetra-O-benzoyl-β-D-galactofuranose；1-O-acetyl-2,3,5,6-tetra-O-benzoyl-D-galactofuranose；[(2R)-2-[(2S,3S,4R,5S)-5-acetyloxy-3,4-dibenzoyloxyoxolan-2-yl]-2-benzoyloxyethyl] benzoate
• CAS: 89825-84-3
• 化学式: C₃₆H₃₀O₁₁
• 分子量: 638.628
• InChiKey: DHKYMCKGIPKWAT-RGLQZYTOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  47
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-O-Acetyl-2,3,4,6-tetra-O-benzoyl-β-galactofuranose 在 氨 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 2,3,5,6-tetra-O-benzoyl-β-D-galactofuranosyl trichloroacetimidate
  参考文献：
  名称：

  First synthesis of β-d-Galf-(1→3)-d-Galp—the repeating unit of the backbone structure of the O-antigenic polysaccharide present in the lipopolysaccharide (LPS) of the genus Klebsiella

  摘要：

  b-D-Galactofuranosyl-(1 --> 3)-D-galactopyranose (1), the repeating unit of the backbone structure of the O-antigenic polysaccharide present in the lipopolysaccharide (LPS) of the genus Klebsiella, has been efficiently synthesized using 1,2:5,6-di-O-isopropylidine-alpha-D-galactofuranose (3) as the glycosyl acceptor and 2,3,5,6-tetra-0-benzoyl-p-D-galactofuranosyl trichloroacetimidate (6) as the glycosyl donor with TMSOTf as catalyst by the well-known Schmidt glycosylation method. The preparation of 3 was improved by increasing the ratio of DMF to acetone and employing a solid-supported catalyst. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00076-4
• 作为产物：
  描述：

  ethyl 1-thio-α-D-galactofuranoside 在 mercury(II) diacetate 作用下， 以 吡啶 为溶剂， 反应 0.17h， 生成 1-O-Acetyl-2,3,4,6-tetra-O-benzoyl-β-galactofuranose
  参考文献：
  名称：

  A synthesis of 1,2-trans-related glycofuranosyl acetates

  摘要：

  DOI：

  10.1016/0008-6215(84)85117-4

文献信息

• The first chemical synthesis of UDP-α-D-galactofuranose
  作者：Yury E. Tsvetkov、Andrei V. Nikolaev

  DOI：10.1039/b000210k

  日期：——

  Uridine 5′-diphosphate α-D-galactofuranose, which is likely to be a biochemical donor of D-galactofuranosyl residues in Nature, is synthesized from α-D-galactofuranosyl phosphate and uridine 5′-monophosphate.

  尿苷5'-二磷酸α-D-半乳糖呋喃糖，可能是自然界中D-半乳糖呋喃糖残基的生物化学供体，由α-D-半乳糖呋喃糖磷酸和尿苷5'-单磷酸合成。
• Ferrier, Robert J.; Haines, Stephen R.; Gainsford, Graeme J., Journal of the Chemical Society. Perkin transactions I, 1984, # 8, p. 1683 - 1687
  作者：Ferrier, Robert J.、Haines, Stephen R.、Gainsford, Graeme J.、Gabe, Eric J.

  DOI：——

  日期：——
• Thiodisaccharides with galactofuranose or arabinofuranose as terminal units: Synthesis and inhibitory activity of an exo β-d-galactofuranosidase
  作者：Evangelina Repetto、Carla Marino、M. Laura Uhrig、Oscar Varela

  DOI：10.1016/j.bmc.2009.02.045

  日期：2009.4

  Thiodisaccharides having beta-D-Galf or alpha-L-Araf units as non-reducing end have been synthesized by the SnCl4- or MoO2Cl2-promoted thioglycosylation of per-O-benzoyl-D-galactofuranose (1), its 1-O-acetyl analogue 4, or per-O-acetyl-alpha-L-arabinofuranose (16) with 6-thioglucose or 6-thiogalactose derivatives. After convenient removal of the protecting groups, the free thiodisaccharides having the basic structure beta-D-Galf(1 -> 6)-6-thio-alpha-D-Glcp-OMe (5) or beta-D-Galf(1 -> 6)-6-thio-alpha-D-Galp-OMe (15) were obtained. The respective alpha-L-Araf analogues 18 and 20 were prepared similarly from 16. Alternatively, beta-D-Galf(1 -> 4)-4-thio- 3-deoxy-alpha-L-Xylp-OiPr was synthesized by Michael addition to a sugar enone of 1-thio-beta-D-Galf derivative, generated in situ from the glycosyl isothiourea derivative of 1. The free S-linked disaccharides were evaluated as inhibitors of the beta-galactofuranosidase from Penicillium fellutanum, being 15 and 20 the more active inhibitors against this enzyme. (c) 2009 Elsevier Ltd. All rights reserved.
• Ferrier, Robert J.; Haines, Stephen R., Journal of the Chemical Society. Perkin transactions I, 1984, # 8, p. 1675 - 1681
  作者：Ferrier, Robert J.、Haines, Stephen R.

  DOI：——

  日期：——