tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-threo-dodeca-8Z-enopyranoside | 167901-88-4

• 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: tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-threo-dodeca-8Z-enopyranoside
• 英文别名: (2R,3R,6R)-2-[(Z)-hept-3-enyl]-6-[(2-methylpropan-2-yl)oxy]-3-phenylmethoxyoxane
• CAS: 167901-88-4
• 化学式: C₂₃H₃₆O₃
• 分子量: 360.537
• InChiKey: WXITURSIZVQICH-IFINOFHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-threo-dodeca-8Z-enopyranoside 在 2,4,6-三甲基吡啶 、 盐酸 、 4 Angstroem MS 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.42h， 生成 trityl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-threo-dodeca-8Z-enopyranoside
  参考文献：
  名称：

  PYRANOSIDE ALKENE TEMPLATES FOR THE SYNTHESIS OF CIS-2,5-DISUBSTITUTED TETRAHYDROFURAN SUBUNITS OF THE ACETOGENINS

  摘要：

  The iodoetherification reaction of t-butyl and trityl glycosides of C6 allylated-2,3-dideoxy-D-erythro- and D-threo-pyranosides was examined as part of a model study aimed at the synthesis of the 2,5-disubstituted tetrahydrofuran subunits found in the acetogenin group of natural products. In general, the t-butyl glycosides gave moderate, and the trityl derivatives, excellent stereoselectivity for the cis THF product.

  DOI：

  10.1081/car-120014903
• 作为产物：
  描述：

  tert-butyl 4-O-benzyl-2,3,6,7,8,9-hexadeoxy-α-D-threo-non-8-enopyranoside 在 sodium hexamethyldisilazane 、 臭氧 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 2.0h， 生成 tert-butyl 4-O-benzyl-2,3,6,7,8,9,10,11,12-nonadeoxy-α-D-threo-dodeca-8Z-enopyranoside
  参考文献：
  名称：

  PYRANOSIDE ALKENE TEMPLATES FOR THE SYNTHESIS OF CIS-2,5-DISUBSTITUTED TETRAHYDROFURAN SUBUNITS OF THE ACETOGENINS

  摘要：

  The iodoetherification reaction of t-butyl and trityl glycosides of C6 allylated-2,3-dideoxy-D-erythro- and D-threo-pyranosides was examined as part of a model study aimed at the synthesis of the 2,5-disubstituted tetrahydrofuran subunits found in the acetogenin group of natural products. In general, the t-butyl glycosides gave moderate, and the trityl derivatives, excellent stereoselectivity for the cis THF product.

  DOI：

  10.1081/car-120014903

文献信息

• cis-2,5-Disubstituted tetrahydrofurans from pyranosides: A novel example of remote stereocontrol by the aglycone
  作者：Huiping Zhang、Phyllis Wilson、Weifang Shan、Zheming Ruan、David R. Mootoo

  DOI：10.1016/0040-4039(94)02342-9

  日期：1995.1

  A stereoselective methodology, based on neighboring group participation by the acetal ring oxygen, is described for the preparation of highly functionalizable cis-2,5-disubstituted tetrahydrofurans from C6 alkenyl branched pyranosides.

  描述了一种基于乙缩醛环氧的邻近基团参与的立体选择性方法，用于从C6烯基支链吡喃糖苷制备高度可官能化的cis-2,5-二取代四氢呋喃。
• PYRANOSIDE ALKENE TEMPLATES FOR THE SYNTHESIS OF <i>CIS</i>-2,5-DISUBSTITUTED TETRAHYDROFURAN SUBUNITS OF THE ACETOGENINS
  作者：Huiping Zhang、Darrin Dabideen、Galyna Pushchinska、David R. Mootoo

  DOI：10.1081/car-120014903

  日期：2002.1.10

  The iodoetherification reaction of t-butyl and trityl glycosides of C6 allylated-2,3-dideoxy-D-erythro- and D-threo-pyranosides was examined as part of a model study aimed at the synthesis of the 2,5-disubstituted tetrahydrofuran subunits found in the acetogenin group of natural products. In general, the t-butyl glycosides gave moderate, and the trityl derivatives, excellent stereoselectivity for the cis THF product.