phenyl 2,3,5,6-tetra-O-acetyl-1-thio-β-D-galactofuranoside | 207131-41-7

• 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: phenyl 2,3,5,6-tetra-O-acetyl-1-thio-β-D-galactofuranoside
• 英文别名: [(2R)-2-acetyloxy-2-[(2S,3S,4R,5S)-3,4-diacetyloxy-5-phenylsulfanyloxolan-2-yl]ethyl] acetate
• CAS: 207131-41-7
• 化学式: C₂₀H₂₄O₉S
• 分子量: 440.471
• InChiKey: VHJGZKPLSNVZIE-CXQPBAHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,5,6-tetra-O-acetyl-1-thio-β-D-galactofuranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成 phenyl-1-thio-β-D-galactofuranoside
  参考文献：
  名称：

  A General and Diastereoselective Synthesis of 1,2-cis-Hexofuranosides from 1,2-trans-Thiofuranosyl Donors

  摘要：

  DOI：

  10.1002/(sici)1099-0690(200004)2000:8<1423::aid-ejoc1423>3.0.co;2-9
• 作为产物：
  描述：

  苯硫酚 、 1,2,3,5,6-penta-O-acetyl-D-galactofuranose 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以81%的产率得到phenyl 2,3,5,6-tetra-O-acetyl-1-thio-β-D-galactofuranoside
  参考文献：
  名称：

  A General and Diastereoselective Synthesis of 1,2-cis-Hexofuranosides from 1,2-trans-Thiofuranosyl Donors

  摘要：

  DOI：

  10.1002/(sici)1099-0690(200004)2000:8<1423::aid-ejoc1423>3.0.co;2-9

文献信息

• Photodegradation of Target Oligosaccharides by Light-Activated Small Molecules
  作者：Daisuke Takahashi、Shingo Hirono、Chigusa Hayashi、Masayuki Igarashi、Yoshio Nishimura、Kazunobu Toshima

  DOI：10.1002/anie.201005161

  日期：2010.12.27

  Shine on, shine on: The designed anthraquinone/boronic acid hybrid 1 selectively caused the degradation of oligosaccharides that have a β‐D‐galactofuranoside residue, which is a unique component in mycobacterial cell walls. Degradation was achieved using long‐wavelength UV radiation in the absence of any additives and under neutral conditions.

  发光，发光：设计的蒽醌/硼酸杂化物1选择性降解具有β- D-半乳糖呋喃糖苷残基的寡糖，这是分枝杆菌细胞壁中的独特成分。在没有任何添加剂的情况下，在中性条件下，使用长波紫外线辐射可实现降解。
• Sulfur atom configuration of sulfinyl galactofuranosides determines different reactivities in glycosylation reactions
  作者：Vincent Ferrières、Jérôme Joutel、Rachel Boulch、Myriam Roussel、Loı̈c Toupet、Daniel Plusquellec

  DOI：10.1016/s0040-4039(00)00887-x

  日期：2000.7

  Sulfinyl β-d-galactofuranosides 3(R,S) and 9(R,S) were used as new hexofuranosyl donors in glycosylation reactions. Activation by trifluoromethanesulfonic anhydride involved different reaction pathways depending on the stereochemistry at the sulfur atom. Experimental results underlined a more suitable reactivity of 3(R) and 9(R) versus 3(S) and 9(S), respectively, for the synthesis of β-d-galactofuranosides

  亚磺酰基β-d-半乳糖呋喃糖苷3（R，S）和9（R，S）被用作糖基化反应中的新的呋喃呋喃糖基供体。三氟甲磺酸酐的活化涉及不同的反应途径，这取决于硫原子的立体化学。实验结果强调了3（R）和9（R）分别比3（S）和9（S）更适合用于合成β-d-半乳糖呋喃糖苷。
• Synthesis of the starfish ganglioside AG2 pentasaccharide
  作者：Shinya Hanashima、Yoshiki Yamaguchi、Yukishige Ito、Ken-ichi Sato

  DOI：10.1016/j.tetlet.2009.08.071

  日期：2009.11

  This Letter reports the first synthesis of the AG2 pentasaccharide, using silylene-oxazolidinone double-locked sialic acid building blocks. The di-DTBS-protected sialic acid building block was easily prepared and readily activated with NIS and TfOH to provide the sialylated lactose unit in good yield with moderate selectivity. After obtaining the trisaccharide unit, the oxazolidinone-protected C4-OH on the sialic acid residue was readily deprotected by treatment with NaOMe. Coupling with the galactofuranosyl beta(1-3)galactopyranosyl fluoride building block produced the desired AG2 pentasaccharide in a highly stereoselective manner. Finally, the desired AG2 pentasaccharide was obtained in good yield following global deprotection. (C) 2009 Elsevier Ltd. All rights reserved.