(1S,3R,4S,5R,6R)-7,7-dichloro-4,5-bis(phenylmethoxy)-3-(phenylmethoxymethyl)-2-oxabicyclo[4.1.0]heptane | 162332-13-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R,4S,5R,6R)-7,7-dichloro-4,5-bis(phenylmethoxy)-3-(phenylmethoxymethyl)-2-oxabicyclo[4.1.0]heptane
• CAS: 162332-13-0
• 化学式: C₂₈H₂₈Cl₂O₄
• 分子量: 499.434
• InChiKey: MLWOPDONKKNNFH-ACFIUOAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,3R,4S,5R,6R)-7,7-dichloro-4,5-bis(phenylmethoxy)-3-(phenylmethoxymethyl)-2-oxabicyclo[4.1.0]heptane 在 吡啶 、 N-碘代丁二酰亚胺 、 lithium aluminium tetrahydride 、 palladium 10% on activated carbon 、 氢气 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 75.0h， 生成 benzyl 4,6-O-benzylidene-3-O-benzoyl-2-deoxy-2-C-(iodomethyl)-β-D-glucopyranoside
  参考文献：
  名称：

  针对碳水化合物酯酶家族4脱N-乙酰酶的单糖抑制剂

  摘要：

  碳水化合物酯酶家族4包含可改变肽聚糖和生物膜相关胞外多糖的毒力因子。尽管该酶家族很重要，但基于机理的有效抑制策略尚未出现。基于假定的四面体脱-N-乙酰化中间体的三齿结合模式，合成了在2和3位带有金属螯合基团的GlcNAc衍生物。这些支架包括2-C膦酸酯，2-C磺酰胺，2-硫代乙酰胺弹头以及在3-位带有巯基，胺和叠氮化物取代基的衍生物。对这些抑制剂针对代表性的肽聚糖脱乙酰酶（来自肺炎链球菌肺炎的Pgda）进行了测定，和代表性的生物膜相关胞外多糖脱乙酰基酶，PgaB从大肠杆菌。在评估的抑制剂中，3-硫代衍生物对Pgda的抑制作用弱到中等。最强的抑制剂是2,3-二甲氧基苄基-2-硫代乙酰胺-3-硫代-β- d-葡萄糖苷，其抑制能力显示出对金属浓度的出乎意料的依赖性，并且发现其具有部分混合抑制模式（K i  = 2.9 ±0.6μM）。

  DOI：

  10.1016/j.bmc.2018.10.008
• 作为产物：
  描述：

  3,4,6-三苄氧基-D-葡萄烯糖 在 sodium hydroxide 、 二甲基二环氧乙烷 作用下， 以 二氯甲烷 为溶剂， 生成 (1S,3R,4S,5R,6R)-7,7-dichloro-4,5-bis(phenylmethoxy)-3-(phenylmethoxymethyl)-2-oxabicyclo[4.1.0]heptane
  参考文献：
  名称：

  Cytotoxic effects of C-glycosides in HOS and HeLa cell lines

  摘要：

  Fifty-two C-glycosides were synthesized and their in-vitro antiproliferative activity screened against human cervical carcinoma (HeLa) and osteosarcoma (HOS) cell lines. Nine of them had growth inhibitions (GI(50) values) below 10 mu M, the Gglucopyranoside 38 being the most active against HeLa (5.4 mu M) and the dichlorocyclopropyl derivative 42 against HOS (1.6 mu M). Some preliminary structure-activity relationships were established. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.060

文献信息

• A New Procedure for Highly Regio‐ and Stereoselective Iodoacetoxylation of Protected Glycals and α‐1,2‐Cyclopropanated Sugars
  作者：David W. Gammon、Henok H. Kinfe、Dirk E. De Vos、Pierre A. Jacobs、Bert F. Sels

  DOI：10.1080/07328300701351524

  日期：2007.5.31

  less than 2 h at low temperatures to 2‐deoxy‐2‐iodoglycosyl acetates or novel 2‐deoxy‐2‐iodomethylglycosyl acetates using the simple, inexpensive reagent mixture of ammonium iodide, hydrogen peroxide, and acetic anhydride/acetic acid in acetonitrile. The protected glycals gave rise to 2‐deoxy‐2‐bromoglycosyl acetates when ammonium bromide was used instead of the iodide, although longer reaction times

  使用简单，廉价的方法，在低温下不到2小时的时间内，可以在不到2小时的时间内以高收率和高选择性将受保护的糖和α-1,2-环丙烷化的糖转化为2-脱氧-2-碘代糖基乙酸酯或新型2-脱氧-2-碘甲基糖基乙酸酯。碘化铵，过氧化氢和乙酸酐/乙酸在乙腈中的试剂混合物。当使用溴化铵代替碘化物时，尽管需要更长的反应时间并且选择性较差，但受保护的糖类会生成2-脱氧-2-溴代糖基乙酸酯。其他简单的烯烃，例如苯乙烯和茚，也被转化为它们相应的1,2-反-碘乙酸酯。
• Synthesis of 1,2-cyclopropanated sugars from glycals
  作者：R. Murali、C. V. Ramana、M. Nagarajan

  DOI：10.1039/c39950000217

  日期：——

  Syntheses of both forms of cyclopropanated sugars from glycals by (i) Simmons–Smith reaction and (ii) dichiorocarbene addition followed by dehalogenation are described.

  描述了通过(i) Simmons–Smith反应和(ii) 二氯甲烯添加后去卤化的方法合成两种形式的环丙烷糖。
• Studies Towards the Synthesis of the C29-C51 Fragment of Altohyrtin A
  作者：Eduardo Fernandez-Megia、Nelly Gourlaouen、Steven V. Ley、Gareth J. Rowlands

  DOI：10.1055/s-1998-3140

  日期：1998.9

  The synthesis of the highly substituted E and F pyran fragment 23 of altohyrtin A 1 from tri-O-benzyl-d-glucal 5 is described. The synthesis of a model compound 31 containing the altohyrtin A triene side-chain outlines the proposed strategy for the elaboration of the F pyran.

  本文介绍了从三-O-苄基-d-葡萄糖醛 5 中合成高度取代的阿尔托黄素 A 1 的 E 和 F 吡喃片段 23 的过程。含有阿托菌素 A 三烯侧链的模型化合物 31 的合成概述了拟议的 F 吡喃化合物的合成策略。
• Synthesis and Reactions of 1,2-Cyclopropanated Sugars
  作者：C. V. Ramana、R. Murali、M. Nagarajan

  DOI：10.1021/jo970948k

  日期：1997.10.1

  Diastereospecific cyclopropanation of glycals 1, 2, 3, 4, and 41 was carried out using either dihalocarbene addition or zinc-carbenoid addition to yield 1,2-cyclopropanated sugars. Dichloro- and dibromocarbenes added stereoselectively anti to the C-3 benzyloxy group, whereas (under Simmons-Smith conditions) the cyclopropanes were formed syn to the same substituent. The reactions of these 1,2-cyclopropanated sugars to provide either ring expanded glycosides or C-2-branched chain glycosides were explored. Solvolytic ring expansion of 1,2-dibromocyclopropanated sugars with K2CO3 in refluxing methanol yielded the corresponding chiral oxepins 20-22. Electrophilic ring openings of parent cyclopropanes (14 and 17 derived from glucal 1) were carried out with different electrophiles to give functionalized 2-deoxy-2-C-branched chain glycosides. The ring openings of 14 in different solvents resulted in both alpha- and beta-anomers, whereas 17 gave exclusively the alpha-anomer.
• Cytotoxic effects of C-glycosides in HOS and HeLa cell lines
  作者：Carlos A. Sanhueza、Carlos Mayato、Rubén P. Machı´n、José M. Padrón、Rosa L. Dorta、Jesús T. Vázquez

  DOI：10.1016/j.bmcl.2007.04.060

  日期：2007.7

  Fifty-two C-glycosides were synthesized and their in-vitro antiproliferative activity screened against human cervical carcinoma (HeLa) and osteosarcoma (HOS) cell lines. Nine of them had growth inhibitions (GI(50) values) below 10 mu M, the Gglucopyranoside 38 being the most active against HeLa (5.4 mu M) and the dichlorocyclopropyl derivative 42 against HOS (1.6 mu M). Some preliminary structure-activity relationships were established. (c) 2007 Elsevier Ltd. All rights reserved.