phenyl 2,3,4,6-tetra-O-benzyl-1-sulfinyl-α/β-D-glucopyranoside | 122795-89-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4,6-tetra-O-benzyl-1-sulfinyl-α/β-D-glucopyranoside
• 英文别名: Phenyl 2,3,4,6-tetra-O-benzyl-1-thio-D-glucopyranoside sulfoxide；2,3,4,6-tetra-O-benzyl-D-glucopyranosyl phenylsulfoxide；Phenyl 2,3,4,6-Tetra-O-benzyl-1-thio-D-glucopyranoside-s-oxide；Phenyl 2,3,4,6-tetra-O-benzyl-1-thio-D-glucopyranoside S-oxide；(3R,4S,5R,6R)-2-(benzenesulfinyl)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 122795-89-5
• 化学式: C₄₀H₄₀O₆S
• 分子量: 648.82
• InChiKey: SZCBPJJRURAJJH-MYRMYZCNSA-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：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  82.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  phenyl 2,3,4,6-tetra-O-benzyl-1-sulfinyl-α/β-D-glucopyranoside 在 palladium on activated charcoal 2,6-二叔丁基-4-甲基吡啶 、 环己烯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 acetosyringyl α-D-glucoside
  参考文献：
  名称：

  Effect of Phenolic Glycosides on Agrobacterium tumefaciens virH Gene Induction and Plant Transformation

  摘要：

  O-Aryl-D-glucoside (4-7) and D-xyloside (8-10) derivatives were synthesized and tested on Agrobacterium virH gene induction and plant transformation. alpha- or beta-Glycosides enhanced vir activity at concentrations above 250 muM. The highest vir activity was observed with beta-glucoside derivative 4 at 10 mM. A marked difference between phenol glucoside derivative 4 and the corresponding free phenol on the growth of transformants was observed. The regenerated transgenic tissues, after transformation on medium containing acetosyringyl beta-glucoside 4, grew at twice the rate of those on medium containing only free acetosyringone (AS). Compound 4 was less toxic for tobacco explants compared to the corresponding free phenol. However, the xyloside derivatives tested (8-10) were less effective for gene induction compared with corresponding free phenols.

  DOI：

  10.1021/np030281z
• 作为产物：
  描述：

  (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 sodium methylate 、 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 phenyl 2,3,4,6-tetra-O-benzyl-1-sulfinyl-α/β-D-glucopyranoside
  参考文献：
  名称：

  Wang, Yali; Zhang, Hong; Voelter, Wolfgang, Zeitschrift fur Naturforschung, B: Chemical Sciences, 1995, vol. 50, # 4, p. 661 - 666

  摘要：

  DOI：

文献信息

• Glycosylated steroid derivatives for transport across biological
  申请人：Trustees of Princeton University

  公开号：US05627270A1

  公开（公告）日：1997-05-06

  Novel glycosylated steroid derivatives for facilitating the transport of compounds across biological membranes, either in admixture or as conjugates, are disclosed. A novel process for efficient synthesis of these glycosylated steroid derivatives, using activated glycosyl sulfoxide intermediates is provided. Methods for the permeabilization of membranes and the enhancement of the activity of predetermined compounds are also provided.

  本发明揭示了一种用于促进化合物通过生物膜的传输的新型糖基化类固醇衍生物，可以作为混合物或结合物使用。本发明还提供了一种高效合成这些糖基化类固醇衍生物的新型方法，使用活性糖基亚砜中间体。本发明还提供了渗透化膜和增强预定化合物活性的方法。
• Tanikawa, Tetsuya; Fridman, Micha; Zhu, Wenjiang, Journal of the American Chemical Society, 2009, vol. 131, p. 5075 - 5083
  作者：Tanikawa, Tetsuya、Fridman, Micha、Zhu, Wenjiang、Faulk, Brian、Joseph, Isaac C.、et al.

  DOI：——

  日期：——
• KAHNE, DANIEL;WALKER, SUZANNE;CHENG, YUAN;ENGEN, DONNA VAN, J. AMER. CHEM. SOC., 111,(1989) N7, C. 6881-6882
  作者：KAHNE, DANIEL、WALKER, SUZANNE、CHENG, YUAN、ENGEN, DONNA VAN

  DOI：——

  日期：——
• Facial amphiphiles
  作者：Yuan Cheng、Douglas M. Ho、Craig R. Gottlieb、Daniel Kahne、Michael A. Bruck

  DOI：10.1021/ja00044a067

  日期：1992.8
• US5795870A
  申请人：——

  公开号：US5795870A

  公开（公告）日：1998-08-18