2,6-anhydro-1,3,4,5-tetra-O-benzyl-7,8,9-trideoxy-D-glycero-L-galacto-non-7,8-dienitol | 140397-44-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-anhydro-1,3,4,5-tetra-O-benzyl-7,8,9-trideoxy-D-glycero-L-galacto-non-7,8-dienitol
• 英文别名: (2R,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-2-(phenylmethoxymethyl)-6-propa-1,2-dienyloxane
• CAS: 140397-44-0
• 化学式: C₃₇H₃₈O₅
• 分子量: 562.706
• InChiKey: QTKAIUIQJUXIAG-GDWCTEMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,6-anhydro-1,3,4,5-tetra-O-benzyl-7,8,9-trideoxy-D-glycero-L-galacto-non-7,8-dienitol 在 sodium tetrahydroborate 、 臭氧 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 异丙醇 为溶剂， 反应 24.0h， 生成 (2',3',4',6'-tetra-O-benzyl-β-D-galactopyranosyl)methyl alcohol
  参考文献：
  名称：

  一种合成α-和β- c-糖基醛的有效方法

  摘要：

  描述了从单一碳水化合物前体合成α-和β- C-糖基醛的实用方法。

  DOI：

  10.1016/s0040-4039(00)77703-3
• 作为产物：
  描述：

  1-O-acetyl-2,3,4,6-tetra-O-benzyl-α-D-galactopyranose 、 炔丙基三甲基硅烷 在 三氟甲磺酸三甲基硅酯 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以87%的产率得到2,6-anhydro-1,3,4,5-tetra-O-benzyl-7,8,9-trideoxy-D-glycero-L-galacto-non-7,8-dienitol
  参考文献：
  名称：

  Ultrasound-assisted synthesis of C-glycosides

  摘要：

  A significant rate enhancement was observed in the preparation of allyl and allenyl-C-glycosides from glycosyl acetate or methyl O-glycoside precursors when ultrasound irradiation was employed as an energy source. The C-glycosides were obtained in 77-96% yields in <20 min using TMSOTf as promoter. These results show that sonication provides rapid and efficient access to useful C-glycoside-based building blocks. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.113

文献信息

• Synthesis of Novel Donor Mimetics of UDP-Gal, UDP-GlcNAc, and UDP-GalNAc as Potential Transferase Inhibitors
  作者：Andreas Schäfer、Joachim Thiem

  DOI：10.1021/jo990766l

  日期：2000.1.1

  For the enzymatic transfer of galactose, N-acetylglucosamine, and N-acetylgalactosamine, UDP-Gal (1), UDP-GlcNAc (2), and UDP-GalNAc (3) are employed, and UDP serves as a feedback inhibitor. In this paper the synthesis of the novel UDP-sugar analogues 4, 5, and 6 as potential transferase inhibitors is described. Compounds 4-6 feature C-glycosidic hydroxymethylene linkages between the sugar and nucleoside

  对于半乳糖，N-乙酰氨基葡糖和N-乙酰半乳糖胺的酶促转移，使用UDP-Gal（1），UDP-GlcNAc（2）和UDP-GalNAc（3），并且UDP用作反馈抑制剂。在本文中，描述了作为潜在转移酶抑制剂的新型UDP-糖类似物4、5和6的合成。与天然衍生物1-3中的异头氧相反，化合物4-6在糖和核苷部分之间具有C-糖苷羟基亚甲基键。
• Synthesis and Conformational Analysis of (α-D-Galactosyl)phenylmethane and α-,β-Difluoromethane Analogues: Interactions with the Plant Lectin Viscumin
  作者：Maria Kolympadi、Marco Fontanella、Chiara Venturi、Sabine André、Hans-Joachim Gabius、Jesús Jiménez-Barbero、Pierre Vogel

  DOI：10.1002/chem.200801394

  日期：2009.3.9

  To bend about: The conformations of three phenyl‐C‐galactosides in solution were evaluated by using theoretical calculations and NMR spectroscopic studies. The α‐CF2 derivative (see scheme) showed significant flexibility of the pyranose ring and around the pseudoanomeric center, whereas the other two analogues more closely resemble the natural galactosides. Regardless, all three compounds bind to a

  弯腰：通过使用理论计算和NMR光谱研究评估了溶液中三种苯基C-半乳糖苷的构象。α-CF 2衍生物（参见方案）显示吡喃糖环和围绕pseudoanomeric中心的显著灵活性，而其它两个类似物更接近于天然半乳糖苷。无论如何，所有这三种化合物都与植物凝集素结合。
• Ultrasound-assisted synthesis of C-glycosides
  作者：Dilip V. Jarikote、Ciaran O’Reilly、Paul V. Murphy

  DOI：10.1016/j.tetlet.2010.10.113

  日期：2010.12

  A significant rate enhancement was observed in the preparation of allyl and allenyl-C-glycosides from glycosyl acetate or methyl O-glycoside precursors when ultrasound irradiation was employed as an energy source. The C-glycosides were obtained in 77-96% yields in <20 min using TMSOTf as promoter. These results show that sonication provides rapid and efficient access to useful C-glycoside-based building blocks. (C) 2010 Elsevier Ltd. All rights reserved.
• An efficient method for the synthesis of α- and β-c-glycosyl aldehydes
  作者：William R. Kobertz、Carolyn R. Bertozzi、Mark D. Bednarski

  DOI：10.1016/s0040-4039(00)77703-3

  日期：1992.2

  A practical method for the synthesis of α- and β-C-glycosyl aldehydes from a single carbohydrate precursor is described.

  描述了从单一碳水化合物前体合成α-和β- C-糖基醛的实用方法。