2-hydroxy-1-[3'-O-acetyl-4'-O-benzyl-2,6-dideoxy-β-D-mannopyranosyl]naphthalene | 1161782-31-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxy-1-[3'-O-acetyl-4'-O-benzyl-2,6-dideoxy-β-D-mannopyranosyl]naphthalene
• 英文别名: 2-hydroxy-1-(3'-O-acetyl-4'-O-benzyl-2,6-dideoxy-β-D-glucopyranosyl)naphthalene
• CAS: 1161782-31-5
• 化学式: C₂₅H₂₆O₅
• 分子量: 406.478
• InChiKey: ZNPRLVAJDBNBQV-KHRGITBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  64.99
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1,3-di-O-acetyl-4-O-benzyl-2,6-dideoxy-α-D-glucose 、 2-萘酚 在 三乙基硅烷 、 碘 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 0.25h， 以85%的产率得到2-hydroxy-1-[3'-O-acetyl-4'-O-benzyl-2,6-dideoxy-β-D-mannopyranosyl]naphthalene
  参考文献：
  名称：

  A Metal-Free β-Stereoselective Synthesis of 2-Deoxy-C-arylglycosides: Synthesis of 5-Aza Analogues of Aquayamycin

  摘要：

  标题：摘要 已开发了一种用于β-立体选择性合成2-去氧-C-芳基糖苷的便捷方案。该反应通过使用I2/Et3SiH在一步中激活糖醋酸酯以生成原位的糖基碘中间体，该中间体被萘酚捕获；随后进行类Fries的O到C糖苷重排，选择性地生成β-C-芳基糖苷。该方法适用于广泛的萘酚基团，并且其实用性已在合成5-氮杂环丙霉素类似物中得到证明。

  DOI：

  10.1055/a-1670-2290

文献信息

• Synthesis of orthogonally protected d-olivoside, 1,3-di-O-acetyl-4-O-benzyl-2,6-dideoxy-d-arabinopyranose, as a C-glycosyl donor
  作者：Hasnah Osman、David S. Larsen、Jim Simpson

  DOI：10.1016/j.tet.2009.03.092

  日期：2009.5

  1,3-Di-O-acetyl-4-O-benzyl-2,6-dideoxy-D-arabinopyranose (11) was synthesised from thiophenyl alpha-D-mannopyranoside (21) in an eight-step sequence. Tosylation of 21 and subsequent reaction with 2,2-dimethoxypropane gave tosylate 22, which upon treatment with lithium aluminium hydride furnished 6-deoxy glycoside 24 and by-product thiophenyl 6-deoxy-2-O-isopropyl-alpha-D-arabinopyranoside. The X-ray crystal structure of the latter was determined. Benzylation of the 4-hydroxyl group of 24 and Subsequent protecting group manipulation gave D-rhamnosyl bromide 29, which on treatment with zinc-copper couple gave the orthogonally protected D-rhamnal 30. Triphenylphosphine hydrogen bromide catalysed addition of acetic acid to 30 furnished the target molecule 11. The scandium(III) triflate promoted reaction of 11 and 2-naphthol gave the corresponding C-glycoside 36 in 86% yield. Crown Copyright (C) 2009 Published by Elsevier Ltd. All rights reserved.