(2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(4-methoxy-phenyl)-tetrahydro-pyran-3-ol | 616239-54-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(4-methoxy-phenyl)-tetrahydro-pyran-3-ol
• 英文别名: (2R,3S,4R,5R,6R)-2-(4-methoxyphenyl)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 616239-54-4
• 化学式: C₃₄H₃₆O₆
• 分子量: 540.656
• InChiKey: HJMPQEJIEBIXEI-KKYNAJBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(4-methoxy-phenyl)-tetrahydro-pyran-3-ol 在 钯 氢气 作用下， 生成 1-methoxy-4-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)benzene
  参考文献：
  名称：

  Stereodirected Synthesis of Aryl α-C-Glycosides from 2-O-Arylsilyl-glucopyranosides

  摘要：

  An efficient procedure for the stereoselective synthesis of aryl (x-C-glycosides is presented. The key step of the method is the intramolecular delivery of the aryl group from a 2-O-aryldialkylsilyl substituent to the anomeric carbon by an electrophilic ipso-desilylation; this process leads exclusively to the product having the 1,2-cis configuration.

  DOI：

  10.1021/ol035529q
• 作为产物：
  描述：

  ((2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-pent-4-enyloxy-tetrahydro-pyran-3-yloxy)-diethyl-(4-methoxy-phenyl)-silane 在 iodonium di(2,4,6-trimethylpyridine) perchlorate 、 4 A molecular sieve 、 四丁基氟化铵 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 6.0h， 以74%的产率得到(2R,3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(4-methoxy-phenyl)-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  Stereodirected Synthesis of Aryl α-C-Glycosides from 2-O-Arylsilyl-glucopyranosides

  摘要：

  An efficient procedure for the stereoselective synthesis of aryl (x-C-glycosides is presented. The key step of the method is the intramolecular delivery of the aryl group from a 2-O-aryldialkylsilyl substituent to the anomeric carbon by an electrophilic ipso-desilylation; this process leads exclusively to the product having the 1,2-cis configuration.

  DOI：

  10.1021/ol035529q

文献信息

• Organo-zinc Promoted Diastereoselective <i>C</i>-Arylation of 1,2-Anhydrosugars from Arylboronic Acids
  作者：Madhu Babu Tatina、Anil Kumar Kusunuru、Debaraj Mukherjee

  DOI：10.1021/acs.orglett.5b02364

  日期：2015.9.18

  alpha-C-arylglycosides can be obtained through the addition of aryl zinc reagents to sugar epoxides. The required aryl zinc nudeophiles can be easily obtained from the corresponding boronic acids by B-Zn exchange and attack sugar 1,2 epoxides in a highly diastereoselective fashion to generate 1,2-cis-alpha-hexapyranosyl aryl glycosides under ligand-and base-free conditions.
• Stereodirected Synthesis of Aryl α-<i>C</i>-Glycosides from 2-<i>O</i>-Arylsilyl-glucopyranosides
  作者：Cyril Rousseau、Olivier R. Martin

  DOI：10.1021/ol035529q

  日期：2003.10.1

  An efficient procedure for the stereoselective synthesis of aryl (x-C-glycosides is presented. The key step of the method is the intramolecular delivery of the aryl group from a 2-O-aryldialkylsilyl substituent to the anomeric carbon by an electrophilic ipso-desilylation; this process leads exclusively to the product having the 1,2-cis configuration.