(2S,3R)-6-methoxy-2-methyloxan-3-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2S,3R)-6-methoxy-2-methyloxan-3-ol
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: CWBJMXOKTZGNEH-GFCOJPQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-6-methoxy-2-methyloxan-3-ol 在 咪唑 、 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Direct Synthesis of 2-Deoxy-β-Glycosides via Anomeric O-Alkylation with Secondary Electrophiles

  摘要：

  An approach for direct synthesis of biologically significant 2-deoxy-beta-glycosides has been developed via O-alkylation of a variety of 2-deoxy-sugar-derived anomeric alkoxides using challenging secondary triflates as electrophiles. It was found a free hydroxyl group at C3 of the 2-deoxy-sugar-derived lactols is required in order to achieve synthetically efficient yields. This method has also been applied to the convergent synthesis of a 2-deoxy-beta-tetrasaccharide.

  DOI：

  10.1021/ja4116956
• 作为产物：
  描述：

  2-methoxy-6-methyl-3,4-dihydro-2H-pyran 在 sodium perborate 、 硼烷 作用下， 生成 (2S,3R)-6-methoxy-2-methyloxan-3-ol
  参考文献：
  名称：

  Perkin communications. Improved synthesis of secondary hydroperoxides from alcohols

  摘要：

  Secondary hydroperoxides have been prepared from secondary alcohols by conversion of the alcohol into its mesylate and subsequent reaction with anhydrous hydrazine followed by hydrogen peroxide and sodium peroxide.

  DOI：

  10.1039/p19910002597

文献信息

• Synthesis and DNA-binding affinity studies of glycosylated intercalators designed as functional mimics of the anthracycline antibiotics
  作者：Wei Shi、Robert S. Coleman、Todd L. Lowary

  DOI：10.1039/b909153j

  日期：——

  ide) via a propargyl linker. The DNA binding affinity of these twelve compounds has been evaluated by using both direct and indirect fluorescence measurements. Compared to Dauno and Dox, the DNA binding affinity of these analogues is weaker. However, both aromatic and aminosugar motifs are critical to DNA binding, with more influence coming from the structural features of the aromatic portion.

  蒽环类抗生素，如道诺霉素（道诺） 和阿霉素（多克斯）是众所周知的临床使用的癌症化疗药物，除其他机制外，它们与 DNA 结合，从而引发一系列生物反应，导致细胞死亡。然而，蒽环类药物具有心脏毒性，耐药性发展迅速，限制了其临床应用。我们在这里报告了一类新型功能性蒽环类药物模拟物的合成和 DNA 结合亲和力，该模拟物由与碳水化合物连接的芳香部分组成 ( 1-12 )。在目标中，芳香核由 2-苯基苯并[ b ]呋喃-3-基组成，2-苯基苯并[ b ]噻吩-3-基,1-甲苯磺酰基-2-苯基吲哚-3-基，或与三个氨基糖之一结合的 2-苯基吲哚-3-基（道诺糖胺,阿考斯胺， 或者4-氨基-2,3,4,6-十四氧基-α- L-吡喃己糖苷）通过炔丙基连接体。这十二种化合物的 DNA 结合亲和力已通过直接和间接荧光测量进行了评估。相比道诺和多克斯，这些类似物的DNA结合亲和力较弱。然而，无论是芳香族还是氨基糖基序对于
• Perkin communications. Improved synthesis of secondary hydroperoxides from alcohols
  作者：Dee Ann Casteel、Kyeong-Eun Jung

  DOI：10.1039/p19910002597

  日期：——

  Secondary hydroperoxides have been prepared from secondary alcohols by conversion of the alcohol into its mesylate and subsequent reaction with anhydrous hydrazine followed by hydrogen peroxide and sodium peroxide.
• Direct Synthesis of 2-Deoxy-β-Glycosides via Anomeric <i>O</i>-Alkylation with Secondary Electrophiles
  作者：Danyang Zhu、Kedar N. Baryal、Surya Adhikari、Jianglong Zhu

  DOI：10.1021/ja4116956

  日期：2014.2.26

  An approach for direct synthesis of biologically significant 2-deoxy-beta-glycosides has been developed via O-alkylation of a variety of 2-deoxy-sugar-derived anomeric alkoxides using challenging secondary triflates as electrophiles. It was found a free hydroxyl group at C3 of the 2-deoxy-sugar-derived lactols is required in order to achieve synthetically efficient yields. This method has also been applied to the convergent synthesis of a 2-deoxy-beta-tetrasaccharide.