(S)-4-Benzyloxy-4-((2R,5R)-5-iodomethyl-tetrahydro-furan-2-yl)-butyraldehyde | 168037-43-2

• 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: (S)-4-Benzyloxy-4-((2R,5R)-5-iodomethyl-tetrahydro-furan-2-yl)-butyraldehyde
• 英文别名: (4S)-4-[(2R,5R)-5-(iodomethyl)oxolan-2-yl]-4-phenylmethoxybutanal
• CAS: 168037-43-2
• 化学式: C₁₆H₂₁IO₃
• 分子量: 388.245
• InChiKey: ODDGLJDYPKYRPT-OWCLPIDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-4-Benzyloxy-4-((2R,5R)-5-iodomethyl-tetrahydro-furan-2-yl)-butyraldehyde 在 sodium tetrahydroborate 、 偶氮二异丁腈 作用下， 以 乙醇 、 苯 为溶剂， 反应 25.0h， 生成 (S)-4-Benzyloxy-4-((2R,5S)-5-butyl-tetrahydro-furan-2-yl)-butan-1-ol
  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：

  trityl 4-O-benzyl-2,3,6,7,8,9-hexadeoxy-D-erythro-non-8-enopyranose 在 iodonium(di-γ-collidine) perchlorate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 0.17h， 生成 (S)-4-Benzyloxy-4-((2R,5S)-5-iodomethyl-tetrahydro-furan-2-yl)-butyraldehyde 、 (S)-4-Benzyloxy-4-((2R,5R)-5-iodomethyl-tetrahydro-furan-2-yl)-butyraldehyde
  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。