methyl 3,6-dideoxy-2-O-(4-methoxybenzyl)-4-O-methoxymethyl-α-D-threo-hex-5-enopyranoside | 226885-90-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 3,6-dideoxy-2-O-(4-methoxybenzyl)-4-O-methoxymethyl-α-D-threo-hex-5-enopyranoside
• 英文别名: (2S,3S,5S)-2-methoxy-5-(methoxymethoxy)-3-[(4-methoxyphenyl)methoxy]-6-methylideneoxane
• CAS: 226885-90-1
• 化学式: C₁₇H₂₄O₆
• 分子量: 324.374
• InChiKey: AWMSFSXIMGSCRP-ULQDDVLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3,6-dideoxy-2-O-(4-methoxybenzyl)-4-O-methoxymethyl-α-D-threo-hex-5-enopyranoside 在 吡啶 、 silver trifluoromethanesulfonate 、 mercury(II) trifluoroacetate 、 sodium hydride 、 溶剂黄146 、 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 silver carbonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 生成 (-)-(6S,7aR)-6-(2',3',4',5'-tetra-O-acetyl-β-D-glucopyranosyl)oxy-7,7a-dihydrobenzofuran-2(4H)-one
  参考文献：
  名称：

  Enantioselective synthesis of phyllanthurinolactone, a leaf-closing substance of Phyllanthus urinaria L., and its analogs toward the development of molecular probes

  摘要：

  We report enantioselective synthesis of phyllanthurinolactone (1), a leaf-closing substance of Phyllanthus urinaria L., and its analogs with sugars other than D-glucose. Structure-activity relationship study using them revealed that the structure of the sugar moiety did not affect their bioactivity at all. This result is very important for the development of molecular probes based on the structure of 1. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.129
• 作为产物：
  描述：

  methyl 2,3-anhydro-4,6-O-benzilidene-α-D-mannopyranoside 在 咪唑 、 lithium aluminium tetrahydride 、 potassium tert-butylate 、 水 、 碘 、 sodium hydride 、 溶剂黄146 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 methyl 3,6-dideoxy-2-O-(4-methoxybenzyl)-4-O-methoxymethyl-α-D-threo-hex-5-enopyranoside
  参考文献：
  名称：

  Enantioselective synthesis of phyllanthurinolactone, a leaf-closing substance of Phyllanthus urinaria L., and its analogs toward the development of molecular probes

  摘要：

  We report enantioselective synthesis of phyllanthurinolactone (1), a leaf-closing substance of Phyllanthus urinaria L., and its analogs with sugars other than D-glucose. Structure-activity relationship study using them revealed that the structure of the sugar moiety did not affect their bioactivity at all. This result is very important for the development of molecular probes based on the structure of 1. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.05.129

文献信息

• Total synthesis of paniculide A from d-glucose
  作者：Seiji Amano、Noriaki Takemura、Masami Ohtsuka、Seiichiro Ogawa、Noritaka Chida

  DOI：10.1016/s0040-4020(99)00096-4

  日期：1999.3

  chiral total synthesis of paniculide A (1), a highly oxygenated sesquiterpene possessing a bisabolane skeleton, starting from D-glucose is described. The two different approaches, both involved Ferrier's carbocyclization reaction to construct the cyclohexane unit in 1, were explored. The first approach, employing the carbocyclization of bicyclic substrate furnished the formal total synthesis. The second

  描述了以D-葡萄糖为原料的手性全合成Paniculide A（1），它是一种具有双水硼烷骨架的高度氧化的倍半萜烯。探索了两种不同的方法，均涉及Ferrier的碳环化反应以构建1中的环己烷单元。采用双环底物的碳环化的第一种方法提供了正式的全合成。第二种方法旨在抑制在第一种方法中观察到的不良副反应，该方法采用了单环底物的碳环化和克莱森重排以形成立体选择性碳-碳键。成功全合成1 揭示了Ferrier的碳环化和Claisen重排相结合对于具有环己烷单元的高度氧化的天然产物的手性合成的有效性。
• Enantioselective synthesis of phyllanthurinolactone, a leaf-closing substance of Phyllanthus urinaria L., and its analogs toward the development of molecular probes
  作者：Yoshifumi Urakawa、Takanori Sugimoto、Hirotaka Sato、Minoru Ueda

  DOI：10.1016/j.tetlet.2004.05.129

  日期：2004.7

  We report enantioselective synthesis of phyllanthurinolactone (1), a leaf-closing substance of Phyllanthus urinaria L., and its analogs with sugars other than D-glucose. Structure-activity relationship study using them revealed that the structure of the sugar moiety did not affect their bioactivity at all. This result is very important for the development of molecular probes based on the structure of 1. (C) 2004 Elsevier Ltd. All rights reserved.