2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl trichloroacetimidate | 176301-74-9

• 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: 2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl trichloroacetimidate
• 英文别名: [(2S,3S,4R,5S)-4,5-diacetyloxy-2-methyl-6-(2,2,2-trichloroethanimidoyl)oxythian-3-yl] acetate
• CAS: 176301-74-9
• 化学式: C₁₄H₁₈Cl₃NO₇S
• 分子量: 450.724
• InChiKey: TVQLTPXVIROHIN-PFFKSSDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl trichloroacetimidate 在 三氟化硼乙醚 、 乙酸肼 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 [(2R,3S,4R,5R)-5-azido-6-hydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-4-[(2R,3S,4R,5S,6S)-3,4,5-triacetyloxy-6-methylthian-2-yl]oxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  含5-硫-1-岩藻糖的血型抗原H 2型和Lewis X（Le x）的合成

  摘要：

  合成了两种血型抗原，分别是H型2和Lewis X三糖，它们含有5-硫基-1-岩藻糖而不是1-岩藻糖。使用2-叠氮基-2-脱氧乳糖衍生物11作为常见的二糖中间体。通过三氯乙亚氨酸酯方法对1，6-脱水-2-叠氮基-2-脱氧乳糖的衍生物的2'-OH和3-OH基团的5-硫-1-岩藻糖基化立体选择性地得到α-连接的三糖。

  DOI：

  10.1016/0040-4039(96)00124-4
• 作为产物：
  描述：

  1,2,3,4-tetra-O-acetyl-5-thio-L-fucose 在 乙酸肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Synthesis of 5-Thio-l-fucose-Containing Disaccharides, as Sequence-Specific Inhibitors, and 2‘-Fucosyllactose, as a Substrate of α-l-Fucosidases

  摘要：

  Four 5-thio-L-fucose-containing disaccharides having alpha(1-->6), alpha(1-->3), alpha(1-->4)GlcNAc, and alpha(1-->2-Gal linkages (compounds 1-4, respectively) were synthesized as potential alpha-L-fucosidase inhibitors. The glycosylation reactions using 2,3,4-tri-O-acetyl-5-thio-L-fucopyranosyl trichloroacetimidate as a glycosyl donor and BF3 . OEt(2) as a catalyst gave mainly alpha-linked disaccharides. Only alpha(1-->2)-linked disaccharide 4 showed inhibitory activity (K-i = 0.21 mM) against Bacillus alpha-L-fucosidase which hydrolyzes the Fuc alpha(1-->2) linkage specifically. The results suggested that sequence specificity of an enzyme could be estimated from the inhibitory activities of the compounds 1-4. In contrast, every disaccharide showed inhibitory activity (K-i = 30-91 mu M) against bovine epididymis alpha-L-fucosidase.

  DOI：

  10.1021/jo961725h

文献信息

• Efficient and stereoselective 1,2-cis glycoside formation of 5-thioaldopyranoses: glycosylation with peracetylated 5-thio-D- arabinopyranosyl and 5-thio-L-fucopyranosyl trichloroacetimidates
  作者：Hironobu Hashimoto、Masayuki Izumi

  DOI：10.1016/s0040-4039(00)74054-8

  日期：1993.7

  Trichloroacetimidate method was proved to be effective for 5-thio-D-arabinopyranosylation and 5-thio-L-fucopyranosylation of N-acetyl-D-glucosaminides and D-galactosides. In these 5-thioglycosylation the neighboring group participation of 2-0-acetyl function was not decisive of anomeric stereoselectivity to give 1,2-cis pseudodisaccharides predominantly. Allyl 2-O-(5-thio-alpha-L-fucopyranosyl)-beta-D-galactopyranoside showed potent inhibitory activity toward alpha-L-fucosidase (Ki = 30muM).
• Affinity of 5-thio-l-fucose-containing lewis X (LeX) trisaccharide analogs to anti-LeX monoclonal antibody
  作者：Osamu Tsuruta、Hideya Yuasa、Hironobu Hashimoto、Sadamu Kurono、Shin Yazawa

  DOI：10.1016/s0960-894x(99)00124-9

  日期：1999.4

  5-Thiofucose-containing Le(X) trisaccharide analogs Gal beta(1,4)5SFuc alpha(1,3)}GlcNAc-OMe (2) and Gal beta(1,4)5SFuc beta(1.3)}GlcNAc-OMe (4) were synthesized via 5-thiofucasylation of methyl 2-azido-lactoside derivative 6 by the trichloroacetimidate method. Inhibitory activity of these analogs for the binding of Le(X) to anti-Le(X) antibody was evaluated by enzyme immunoassay, indicating that anti-Le(X) strictly recognizes alpha-configuration of the fucose moiety and its binding pocket includes no advantageous region, such as hydrophobic area, for recognizing the ring sulfur atom of 5-thiofucosyl Le(X) analog 2. (C) 1999 Elsevier Science Ltd. All rights reserved.