(2'S,3'S)-ethyl 3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-glucopyranoside | 197644-79-4

• 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 3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-glucopyranoside
• 英文别名: (2S,3S,4aR,5R,7S,8R,8aR)-7-ethylsulfanyl-5-(hydroxymethyl)-2,3-dimethoxy-2,3-dimethyl-5,7,8,8a-tetrahydro-4aH-pyrano[3,4-b][1,4]dioxin-8-ol
• CAS: 197644-79-4
• 化学式: C₁₄H₂₆O₇S
• 分子量: 338.422
• InChiKey: DGBRPKBQNNXXFX-BIMSSTTISA-N

物化性质

• 沸点：
  485.1±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2'S,3'S)-ethyl 3,4-di-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thio-β-D-glucopyranoside 在 Grubbs catalyst first generation 、 platinum(IV) oxide 吡啶 、 三氟甲磺酸 、 四丁基氟化铵 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 37.25h， 生成 (2''S,3''S) 3-O-(2'-O-benzyl-3',4'-di-O-(2'',3''-dimethoxybutane-2'',3''-diyl)-α-D-glucopyranosyl)-5,6'-di-O-(butane-1,4-diyl)-1,2-O-isopropylidene-α-D-ribofuranoside
  参考文献：
  名称：

  Cyclophostin的合成和生物学评估：腺苷A的5'，6''系绳类似物

  摘要：

  描述了5'-6''系腺苷A，即所谓的环磷蛋白14及其去腺苷酸类似物15的合成，构象分析和生物学评估。它们通过二烯烃28的闭环易位，中心结构单元33分别连续地偶联至6- N-苯甲酰腺嘌呤或炔丙醇，随后进行磷酸化和脱保护而制备。NMR光谱和分子动力学模拟表明，5'-6“-tether诱导从2'-的构象变化内/ SYN在1至3'-内型/抗在14。与环核糖蛋白15相比，低EC 50 / IC 50比反映出环磷蛋白14的Ca 2+释放出乎意料的小损失，这表明腺嘌呤与IP 3 R的相互作用在确定环磷酰胺14中起着决定性作用。腺苷A的高活性（1）。

  DOI：

  10.1016/s0040-4020(00)00480-4
• 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 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 (2'S,3'S)-ethyl 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

• β-Selective Glycosylation Using Axial-Rich and 2-<i>O</i>-Rhamnosylated Glucosyl Donors Controlled by the Protecting Pattern of the Second Sugar
  作者：Masafumi Bando、Yuri Kawasaki、Osamu Nagata、Yasunori Okada、Daiki Ikuta、Kazutada Ikeuchi、Hidetoshi Yamada

  DOI：10.1248/cpb.c20-00733

  日期：2021.1.1

  Herein, we describe two counterexamples of the previously reported β/α-selectivity of 96/4 for glycosylation using ethyl 2-O-[2,3,4-tris-O-tert-butyldimethylsilyl (TBS)-α-L-rhamnopyranosyl]-3,4,6-tris-O-TBS-thio-β-D-glucopyranoside as the glycosyl donor. Furthermore, we investigated the effects of protecting group on the rhamnose moieties in the glycosylation with cholestanol and revealed that β-selectivity originated from the two TBS groups at the 3-O and 4-O positions of rhamnose. In contrast, the TBS group at the 2-O position of rhamnose hampered the β-selectivity. Finally, the β/α-selectivity during the glycosylation was enhanced to ≥99/1. The results obtained herein suggest that the protecting groups on the sugar connected to the 2-O of a glycosyl donor with axial-rich conformation can control the stereoselectivity of glycosylation.

  本文描述了先前报道的β/α-选择性为96/4的两个反例，使用乙基2-O-[2,3,4-三-O-叔丁基二甲基硅基(TBS)-α-L-鼠李糖吡喃糖苷]-3,4,6-三-O-TBS-硫代-β-D-葡萄糖吡喃糖苷作为糖基供体进行糖基化。此外，我们研究了胆固醇醇糖基化中鼠李糖部分保护基的影响，并揭示了β-选择性源于鼠李糖的3-O和4-O位置上的两个TBS基团。相比之下，鼠李糖2-O位置上的TBS基团阻碍了β-选择性。最终，糖基化过程中的β/α-选择性提高至≥99/1。本文获得的结果表明，与轴向富集构象的糖基供体的2-O相连的糖上的保护基可以控制糖基化的立体选择性。
• 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。