(3S,4R,5S,6R)-3,5-dibenzyloxy-4,7-dihydroxy-6-(4-methoxybenzyl)oxyhept-1-ene | 669053-65-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3S,4R,5S,6R)-3,5-dibenzyloxy-4,7-dihydroxy-6-(4-methoxybenzyl)oxyhept-1-ene
• 英文别名: 1,2-dideoxy-6-O-(4-methoxybenzyl)-3,5-di-O-benzyl-D-gluco-hept-1-enitol；(2R,3S,4R,5S)-2-[(4-methoxyphenyl)methoxy]-3,5-bis(phenylmethoxy)hept-6-ene-1,4-diol
• CAS: 669053-65-0
• 化学式: C₂₉H₃₄O₆
• 分子量: 478.585
• InChiKey: XZZWCGSFCJGKSO-AMSOURPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,4R,5S,6R)-3,5-dibenzyloxy-4,7-dihydroxy-6-(4-methoxybenzyl)oxyhept-1-ene 在 2,2'-联苯二甲酸 、 diphenylammonium triflate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以79%的产率得到3,6-anhydro-5-O-benzyl-1,2-dideoxy-D-manno-hept-1-enitol
  参考文献：
  名称：

  Highly stereoselective synthesis of C-vinyl furanosides through acid-catalyzed SN2 inversion at the C-3 position of 1,2-dideoxy-hept-1-enitols

  摘要：

  A highly stereoselective synthesis of C-vinyl furamosides through the S(N)2 inversion at the C-3 position of the 1,2-dideoxy-hept-1-enitols is disclosed. Treatment of the 1,2-dideoxy-hept-1-enitols with diphenylammonium trifluoromethanesulfonate as the acid catalyst produced the C-vinyl furanosides (3,6-anhydro-1,2-dideoxy-hept-1-enitol derivatives) via a subsequent S(N)2 intramolecular debenzyloxyationcycloetherification reaction at the C-3 position. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.08.017
• 作为产物：
  描述：

  1-硫代-b-D-吡喃葡萄糖苷对甲苯酯 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 38.33h， 生成 (3S,4R,5S,6R)-3,5-dibenzyloxy-4,7-dihydroxy-6-(4-methoxybenzyl)oxyhept-1-ene
  参考文献：
  名称：

  The first construction of a 3,6-bridged ellagitannin skeleton with 1C4/B glucose core; synthesis of nonamethylcorilagin

  摘要：

  The synthesis of nonamethylcorilagin is described. In the synthesis, the intramolecular Ullmann coupling afforded the (R)-hexahydroxydiphenoyl part-a characteristic bridge structure of the target molecule-when the glucopyranose ring was opened in advance. This synthesis demonstrates the first synthetic approach to a 3,6-bridged ellagitannin skeleton whose conformation of the D-glucose core is C-1(4) or skew boat. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.006

文献信息

• 3, 6-O-BRIDGED PYRANOSE INVERSION COMPOUND AND PROCESS FOR PRODUCING B-O-PYRANOSIDE
  申请人：Yamada Hidetoshi

  公开号：US20100324275A1

  公开（公告）日：2010-12-23

  An object of the present invention is to provide a 3,6-O-bridged pyranose-inverted compound useful for being easy to produce β-O-pyranosides selectively. The 3,6-O-bridged pyranose-inverted compound according to the present invention is represented by General Formula (1): wherein R A and R B each represent hydrogen or are bonded to each other to form a benzene ring; one of R C and R D represents hydrogen and the other represents —OR 2 ; R 1 represents hydroxy or halogen; and R 2 and R 3 each represent a hydroxy-protecting group.

  本发明的一个目的是提供一种3,6-O-桥联吡喃糖倒置化合物，用于易于选择性地生产β-O-吡喃糖苷。根据本发明，3,6-O-桥联吡喃糖倒置化合物由通式（1）表示：其中RA和RB分别表示氢原子或结合在一起形成苯环；RC和RD中的一个表示氢原子，另一个表示—OR2；R1表示羟基或卤素；R2和R3各自表示一个羟基保护基团。
• Completely β-Selective Glycosylation Using 3,6-<i>O</i>-(<i>o</i>-Xylylene)-Bridged Axial-Rich Glucosyl Fluoride
  作者：Yasunori Okada、Noriaki Asakura、Masafumi Bando、Yoshiki Ashikaga、Hidetoshi Yamada

  DOI：10.1021/ja301480g

  日期：2012.4.25

  A completely β-selective glycosylation that does not rely on neighboring group participation is described. The novelty of this work is the design of the glycosyl donor locked into the axial-rich form by the o-xylylene bridge between the 3-O and 6-O of d-glucopyranose. The synthesized 2,4-di-O-benzyl-3,6-O-(o-xylyene)glucopyranosyl fluoride could efficiently react with various alcohols in a SnCl(2)-AgB(C(6)F(5))(4)

  描述了一种不依赖于相邻基团参与的完全 β 选择性糖基化。这项工作的新颖之处在于设计的糖基供体通过 d-吡喃葡萄糖的 3-O 和 6-O 之间的邻二甲苯桥锁定为富含轴向的形式。合成的 2,4-di-O-benzyl-3,6-O-(o-xylyene) 吡喃葡萄糖基氟可以有效地与 SnCl(2)-AgB(C(6)F(5))( 4）催化体系。通过使用酸性和碱性分子筛的比较实验揭示了由糖基化和异构化循环组成的机制。实现的完美立体控制归因于富含轴向的构象和由原位生成的 HB(C(6)F(5))(4) 引起的收敛异构化的协同作用。
• Total Synthesis of (−)-Corilagin
  作者：Hidetoshi Yamada、Kohei Nagao、Kazutoyo Dokei、Yusuke Kasai、Naoki Michihata

  DOI：10.1021/ja803111z

  日期：2008.6.18

  The synthesis of corilagin was achieved by the integration of the development of the oxidative coupling of the symmetrically protected gallates and the temporarily ring-opened synthetic route for the 3.6-hexahydroxydiphenoyl (HHDP) bridge. This is the first total synthesis of the C-1(4)/B-ellagitannins, which contain ring-flipped glucose.
• US8445652B2
  申请人：——

  公开号：US8445652B2

  公开（公告）日：2013-05-21
• Highly stereoselective synthesis of C-vinyl furanosides through acid-catalyzed SN2 inversion at the C-3 position of 1,2-dideoxy-hept-1-enitols
  作者：Hitoshi Tsuchiya、Noriaki Asakura、Yasunori Ikeda、Hidetoshi Yamada

  DOI：10.1016/j.carres.2008.08.017

  日期：2008.11

  A highly stereoselective synthesis of C-vinyl furamosides through the S(N)2 inversion at the C-3 position of the 1,2-dideoxy-hept-1-enitols is disclosed. Treatment of the 1,2-dideoxy-hept-1-enitols with diphenylammonium trifluoromethanesulfonate as the acid catalyst produced the C-vinyl furanosides (3,6-anhydro-1,2-dideoxy-hept-1-enitol derivatives) via a subsequent S(N)2 intramolecular debenzyloxyationcycloetherification reaction at the C-3 position. (C) 2008 Elsevier Ltd. All rights reserved.