(2'S,3'S)-ethyl 2,6-di-O-benzyl-3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-glucopyranoside | 197644-80-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2'S,3'S)-ethyl 2,6-di-O-benzyl-3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-glucopyranoside
• 英文别名: Ethyl (2'S,3'S)-2,6-di-O-benzyl-3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-glucopyranoside；(2S,3S,4aR,5R,7S,8R,8aS)-7-ethylsulfanyl-2,3-dimethoxy-2,3-dimethyl-8-phenylmethoxy-5-(phenylmethoxymethyl)-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxine
• CAS: 197644-80-7
• 化学式: C₂₈H₃₈O₇S
• 分子量: 518.672
• InChiKey: UJVRZSOOOKLFRJ-IHOPFQFDSA-N

物化性质

• 熔点：
  78-80 °C
• 沸点：
  604.6±55.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  89.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2'S,3'S)-ethyl 2,6-di-O-benzyl-3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-glucopyranoside 在 三氟甲磺酸三甲基硅酯 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 四氯化锡 、 溶剂黄146 作用下， 以 1,4-二氧六环 、 吡啶 、 水 、 乙二醇 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 22.75h， 生成 1-((3-benzyloxycarbonylamino)-propyl)-2-O-acetyl-5-O-benzyl-3-O-(3',4'-di-O-acetyl-2',6'-di-O-benzyl-α-D-glucopyranosyl)-β-D-ribofuranoside
  参考文献：
  名称：

  Synthesis of Photoaffinity Derivatives of Adenophostin A

  摘要：

  DOI：

  10.1002/1099-0690(200009)2000:17<3085::aid-ejoc3085>3.0.co;2-a
• 作为产物：
  描述：

  ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 在 甲醇 、 camphor-10-sulfonic acid 、 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.25h， 生成 (2'S,3'S)-ethyl 2,6-di-O-benzyl-3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Potent Agonists of the d-myo-Inositol 1,4,5-Trisphosphate Receptor Based on Clustered Disaccharide Polyphosphate Analogues of Adenophostin A

  摘要：

  Clustered disaccharide analogues of adenophostin A (2), i.e. mono-, di-, and tetravalent derivatives 6-8, respectively, were synthesized and evaluated as novel ligands for the tetrameric D-myo-inositol 1,4,5-trisphosphate receptor (IP3R). The synthesis was accomplished via Sonogashira coupling of propargyl 2-O-acetyl-5-O-benzyl-3-O-(3,4-di-O-acetyl-2,6-di-O-benzyl-alpha-D-glucopyranosyl)-beta-D-ribofuranoside (16) with iodobenzene 18, 22, or 25, followed by deacetylation, phosphorylation, and deprotection. The abilities of the target compounds 6-8, as well as ribophostin 4, propylphostin 5, and IP3 (1), to evoke Ca2+ release from permeabilized hepatocytes or displacement of [H-3]IP3 from its receptor in hepatic membranes were compared. Although the binding affinities of 4-8 were similar, there were modest though significant differences in their potencies in Ca2+ release assays: tetraphostin 8 > IP3 similar to diphostin 7 > phenylphostin 6 > ribophostin 4 similar to propylphostin 5.

  DOI：

  10.1021/jm000957c

文献信息

• Synthesis of Clustered Disaccharide Polyphosphate Analogues of Adenophostin A
  作者：Martin de Kort、A.Rob P.M. Valentijn、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1016/s0040-4039(97)01811-x

  日期：1997.10

  Three new potential ligands for the IP3 receptor (i.e. compounds 5–7) were prepared by Sonogashira coupling of propargyl 2-O-acetyl-5-O-benzyl-3-O-(3,4-di-O-acetyl-2,6-di-O-benzyl-α-d- glycopyranosyl)-β-d-ribofuranoside (15) with iodobenzene, 1,2-diiodobenzene and 1,2,4,5-tetraiodobenzene, followed by deacetylation, phosphorylation and deprotection. © 1997 Elsevier Science Ltd.

  通过炔丙基2 - O-乙酰基-5- O-苄基-3- O-（3,4-二-O-乙酰基- ）的Sonogashira偶联，制备了IP 3受体的三个新的潜在配体（即化合物5-7）。2,6-二-O-苄基-α-d-吡喃葡萄糖基）-β-d-呋喃核糖苷（15）与碘苯，1,2-二碘苯和1,2,4,5-四碘苯，然后进行脱乙酰基化，磷酸化和脱保护。©1997爱思唯尔科学有限公司。
• Spirophostins: Conformationally Restricted Analogues of Adenophostin A
  作者：Martin de Kort、Anouk D. Regenbogen、A. Rob P. M. Valentijn、R. A. John Challiss、Yoriko Iwata、Shuichi Miyamoto、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1002/1521-3765(20000804)6:15<2696::aid-chem2696>3.0.co;2-y

  日期：2000.8.4

  The synthesis, biological evaluation, and molecular modeling of two conformationally restricted analogues of adenophostin A (1), denominated as spirophostin (3R)-10 and (3S)-11, as novel ligands for the D-myo-inositol 1,4,5-trisphosphate receptor (IP3R), is presented, These diastereoisomeric Spiroketals are synthesized by spiroketalization of D-glucose derivatives (2S)-15 and (2R)-16, separation of the protected isomers (3R)-19 and (3S)-20, followed by phosphorylation and deprotection, The spirophostins (3R)-10 and (3S)-11 display comparable biological activity, with a H-3-IP3-displacing and Ca2+-releasing potency less than IP3 and adenophostin A.