(2S,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-(iodomethyl)-6-methoxytetrahydro-2H-pyran | 176018-12-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-(iodomethyl)-6-methoxytetrahydro-2H-pyran
• 英文别名: methyl 2,3,4-tri-O-benzyl-6-deoxy-6-iodo-D-galactopyranoside；(2S,3R,4S,5R)-2-(iodomethyl)-6-methoxy-3,4,5-tris(phenylmethoxy)oxane
• CAS: 176018-12-5
• 化学式: C₂₈H₃₁IO₅
• 分子量: 574.456
• InChiKey: ZONZORQBUQHJKK-PBVUBXADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-(iodomethyl)-6-methoxytetrahydro-2H-pyran 在 吡啶 、 sodium tetrahydroborate 、 sodium iodide 、 锌 作用下， 以 六甲基磷酰三胺 为溶剂， 生成 3,4,5-tri-O-benzyl-1,2,6-trideoxy-6-iodo-L-lyxo-hex-1-enitol
  参考文献：
  名称：

  A New Synthesis of Carbapentofuranoses from Carbohydrates

  摘要：

  Carbafuranosides were synthesized in one step from various O-protected 1,2,6-trideoxydiodo-hex-1-enitols by cobalt catalyzed 5-exo radical-cyclization under molecular oxygen. Yields were fair to good with interesting selectivities. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01395-6
• 作为产物：
  描述：

  (4aR,7R,8R,8aR)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol 在 lithium aluminium tetrahydride 、 三氯化铝 作用下， 生成 (2S,3R,4S,5R)-3,4,5-tris(benzyloxy)-2-(iodomethyl)-6-methoxytetrahydro-2H-pyran
  参考文献：
  名称：

  离子液体中不饱和硝基的1,3-偶极环加成反应的研究

  摘要：

  已经研究了介质（非手性和手性离子液体）对D-半乳糖衍生的ω-不饱和硝酮的分子内1,3-偶极环加成反应的立体化学的影响，导致双环异恶唑烷。

  DOI：

  10.1080/15257770600793851

文献信息

• Stereoselective SmI2-mediated conversion of carbohydrates into cyclopentanols
  作者：J.J. CronjéGrové、Cedric W. Holzapfel、D.Bradley G. Williams

  DOI：10.1016/0040-4039(95)02380-1

  日期：1996.2

  Carbohydrate derivatives were employed as precursors in the synthesis of stereodefined cyclopentanols. This rapid conversion was effected by a zinc-assisted Grob-fragmentation, followed by a stereocontrolled SmI2-mediated cyclisation.

  碳水化合物衍生物被用作合成立体确定的环戊醇的前体。这种快速转化是通过锌辅助的Grob片段化，然后进行立体控制的SmI 2介导的环化作用来实现的。
• Stereoselective and regioselective one-pot synthesis of polyhydroxy bicyclic diazenes and hydrazones from methyl 6-deoxy-6-iodo-hexosides
  作者：Yunfeng Li、Yao Meng、Zhongjun Li、Xiangbao Meng

  DOI：10.1016/j.tet.2015.05.105

  日期：2015.8

  An efficient, stereoselective, and base-controlled procedure for the preparation of polyhydroxy bicyclic diazenes and polyhydroxy bicyclic hydrazones is described, starting from sugar-derived methyl 6-deoxy6-iodo-hexosides. The one-pot synthesis involves a three-step reaction, including ring-opening, condensation with tosylhydrazine, and intramolecular cycloaddition with terminal alkene, which affords important synthetic precursors of bicyclic diazenes and hydrazones. (C) 2015 Elsevier Ltd. All rights reserved.