2,3,4-tri-O-benzoyl-D-xylopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate | 484002-04-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-benzoyl-D-xylopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate
• 英文别名: [(3R,4S,5R)-4,5-dibenzoyloxy-6-[N-phenyl-C-(trifluoromethyl)carbonimidoyl]oxyoxan-3-yl] benzoate
• CAS: 484002-04-2
• 化学式: C₃₄H₂₆F₃NO₈
• 分子量: 633.578
• InChiKey: LPUXSHUZHKFVRW-VZTHRJCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  46
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzoyl-D-xylopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate 、 diosgenin-3-yl 2,3-di-O-acetyl-6-O-(2,3,4-tri-O-benzoyl-L-arabpyranosyl)-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到diosgenin-3-yl 2,3-di-O-acetyl-6-O-(2,3,4-tri-O-benzoyl-L-arabpyranosyl)-D-glucopyranoside
  参考文献：
  名称：

  Glycosyl Trifluoroacetimidates. 2. Synthesis of Dioscin and Xiebai Saponin I

  摘要：

  Two trisaccharide steroidal saponins, dioscin (1) and Xiebai saponin 1 (2) with various bioactivities, were efficiently synthesized using the newly developed glycosyl N-phenyl trifluoroacetimidates (10-13) as glycosylation donors. Thus, dioscin was synthesized in five steps and a 33% overall yield from diosgenin and glycosyl trifluoroacetimidates (10 and 11). Xiebai saponin I was synthesized in eight steps and a 32% overall yield from laxogenin and glycosyl trifluoroacetimidates (10, 12, and 13), whereupon, the rare steroid laxogenin was prepared from diosgenin in four steps and an overall 69% yield. All the glycosylation reactions involved in the present syntheses demonstrated that glycosyl trifluoroacetimidates were successful donors comparable to the corresponding glycosyl trichloroacetimidates.

  DOI：

  10.1021/jo026103c
• 作为产物：
  描述：

  2,2,2-三氟-N-苯基亚氨代乙酰氯 、 2,3,4-tri-O-benzoyl-L-arabinopyranose 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 2,3,4-tri-O-benzoyl-D-xylopyranosyl 1-(N-phenyl)-2,2,2-trifluoroacetimidate
  参考文献：
  名称：

  Synthesis of a typical N-acetylglucosamine-containing saponin, oleanolic acid 3-yl α-l-arabinopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→6)-2-acetamido-2-deoxy-β-d-glucopyranoside

  摘要：

  Oleanolic acid 3-yl alpha-L-arabinopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl-(1 --> 6)-2-acetamido-2-deoxy-beta-D-glucopyranoside, a cytotoxic saponin isolated from Acacia tenuifolia and Albizia subdimidiata with a typical structure of the N-acetylglucosamine-containing plant saponins, was synthesized. The synthesis adopted a stepwise glycosylation fashion employing glycosyl trifluoroacetimidates 5 and 9 and thioglycoside 12 as donors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00047-8

文献信息

• Chemo‐Enzymatic Synthesis of Long‐Chain Oligosaccharides for Studying Xylan‐Modifying Enzymes
  作者：Ignacio Álvarez‐Martínez、Colin Ruprecht、Deborah Senf、Hsin‐tzu Wang、Breeanna R. Urbanowicz、Fabian Pfrengle

  DOI：10.1002/chem.202203941

  日期：——

  Xylan biosynthesis: Starting from dixylosides, chemo-enzymatic syntheses of xylan dodecasaccharides using glycosynthase-mediated coupling reactions between glycosyl fluoride donors and thioglycoside acceptors were performed. These long-chain xylan oligosaccharides were incubated with xylan-modifying enzymes from plants, i. e., three glycosyltransferases and one acetyltransferase, and the reaction products

  木聚糖生物合成：从双木糖苷开始，使用糖基氟化物供体和硫苷受体之间的糖基合成酶介导的偶联反应，进行了木聚糖十二糖的化学酶促合成。这些长链木聚糖寡糖与来自植物的木聚糖修饰酶一起孵育，即。即，三种糖基转移酶和一种乙酰转移酶，反应产物通过 MALDI-MS 进行分析。
• Glycosyl Trifluoroacetimidates. 2. Synthesis of Dioscin and Xiebai Saponin I
  作者：Biao Yu、Houchao Tao

  DOI：10.1021/jo026103c

  日期：2002.12.1

  Two trisaccharide steroidal saponins, dioscin (1) and Xiebai saponin 1 (2) with various bioactivities, were efficiently synthesized using the newly developed glycosyl N-phenyl trifluoroacetimidates (10-13) as glycosylation donors. Thus, dioscin was synthesized in five steps and a 33% overall yield from diosgenin and glycosyl trifluoroacetimidates (10 and 11). Xiebai saponin I was synthesized in eight steps and a 32% overall yield from laxogenin and glycosyl trifluoroacetimidates (10, 12, and 13), whereupon, the rare steroid laxogenin was prepared from diosgenin in four steps and an overall 69% yield. All the glycosylation reactions involved in the present syntheses demonstrated that glycosyl trifluoroacetimidates were successful donors comparable to the corresponding glycosyl trichloroacetimidates.
• Synthesis of a typical N-acetylglucosamine-containing saponin, oleanolic acid 3-yl α-l-arabinopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→6)-2-acetamido-2-deoxy-β-d-glucopyranoside
  作者：Jiansong Sun、Xiuwen Han、Biao Yu

  DOI：10.1016/s0008-6215(03)00047-8

  日期：2003.4

  Oleanolic acid 3-yl alpha-L-arabinopyranosyl-(1 --> 2)-alpha-L-arabinopyranosyl-(1 --> 6)-2-acetamido-2-deoxy-beta-D-glucopyranoside, a cytotoxic saponin isolated from Acacia tenuifolia and Albizia subdimidiata with a typical structure of the N-acetylglucosamine-containing plant saponins, was synthesized. The synthesis adopted a stepwise glycosylation fashion employing glycosyl trifluoroacetimidates 5 and 9 and thioglycoside 12 as donors. (C) 2003 Elsevier Science Ltd. All rights reserved.