(2R,4aR,6S,7R,8S,8aR)-7-[(2S,3R,4R,5S,6R)-3-iodo-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-6-methoxy-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine | 871948-28-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4aR,6S,7R,8S,8aR)-7-[(2S,3R,4R,5S,6R)-3-iodo-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-6-methoxy-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 871948-28-6
• 化学式: C₄₈H₅₁IO₁₀
• 分子量: 914.831
• InChiKey: JRURPUCYVYGEHU-MOTNTRQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  59
• 可旋转键数：
  17
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  、 methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 作用下， 以69%的产率得到(2R,4aR,6S,7R,8S,8aR)-7-[(2S,3R,4R,5S,6R)-3-iodo-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-6-methoxy-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
  参考文献：
  名称：

  Highly reactive 2-deoxy-2-iodo-d-allo and d-gulo pyranosyl sulfoxide donors ensure β-stereoselective glycosylations with steroidal aglycones

  摘要：

  高度立体选择性合成具有d-xylo和d-ribo构型的具有挑战性的类固醇2-去氧-β-糖苷，通过低温激活2-去氧-2-碘基葡萄糖苷磺酰氧化物实现。

  DOI：

  10.1039/c8ra06619a

文献信息

• Recent advances in the synthesis of 2-deoxy-glycosides
  作者：Dianjie Hou、Todd L. Lowary

  DOI：10.1016/j.carres.2009.07.013

  日期：2009.10

  Glycosides of 2-deoxy-sugars, monosaccharides in which the hydroxyl group at C-2 is replaced with a hydrogen atom, occur widely in natural products and therefore have been the subject of intense synthetic activity. The report summarizes recent advances in this area, with a particular focus on work published since an earlier review on the topic, in 2000 (Marzabadi, C. H.: Franck, R. W. Tetrahedron 2000, 56, 8385-8417). (C) 2009 Elsevier Ltd. All rights reserved.