2-((2R,4aR,6S,8R,8aS)-8-Benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxymethyl)-benzoic acid | 532959-26-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 2-((2R,4aR,6S,8R,8aS)-8-Benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxymethyl)-benzoic acid
• 英文别名: 2-[[(2R,4aR,6S,8R,8aS)-2-phenyl-8-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxymethyl]benzoic acid
• CAS: 532959-26-5
• 化学式: C₂₈H₂₈O₇
• 分子量: 476.526
• InChiKey: PPOCAGMGQCKTLF-DNAQHQBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 、 2-((2R,4aR,6S,8R,8aS)-8-Benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxymethyl)-benzoic acid 在 2,6-二叔丁基-4-甲基吡啶 、 三氟甲磺酸酐 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到methyl 2,3,6-tri-O-benzyl-4-O-(3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Recent advances in the synthesis of 2-deoxy-glycosides

  摘要：

  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.

  DOI：

  10.1016/j.carres.2009.07.013
• 作为产物：
  描述：

  2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl bromide 在 palladium on activated charcoal 4 A molecular sieve 、 camphor-10-sulfonic acid 、 ammonium acetate 、 氢气 、 sodium methylate 、 氰化汞 、 sodium hydride 、 mercury dibromide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 3.66h， 生成 2-((2R,4aR,6S,8R,8aS)-8-Benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxymethyl)-benzoic acid
  参考文献：
  名称：

  1-（2'-羧基）苄基2-脱氧糖苷在直接构建2-脱氧糖基键中作为糖基供体的双重立体选择性。

  摘要：

  DOI：

  10.1002/anie.200390139

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.
• Dual Stereoselectivity of 1-(2′-Carboxy)benzyl 2-Deoxyglycosides as Glycosyl Donors in the Direct Construction of 2-Deoxyglycosyl Linkages
  作者：Kwan Soo Kim、Jin Park、Yong Joo Lee、Yong Sung Seo

  DOI：10.1002/anie.200390139

  日期：2003.1.27