4-methyl-3-[(2S,3R,4S,5R,6R)-2-naphthalen-2-yloxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]sulfanylpent-3-en-2-one | 185836-62-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methyl-3-[(2S,3R,4S,5R,6R)-2-naphthalen-2-yloxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]sulfanylpent-3-en-2-one
• CAS: 185836-62-8
• 化学式: C₄₃H₄₄O₆S
• 分子量: 688.885
• InChiKey: YXQZSYGSQASUSI-NXOVYTTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  50
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  88.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-methyl-3-[(2S,3R,4S,5R,6R)-2-naphthalen-2-yloxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]sulfanylpent-3-en-2-one 在 镍 作用下， 以 乙醇 、 苯 为溶剂， 反应 1.0h， 以12 mg的产率得到2-naphthyl 3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Novel Bicylic Donors for the Synthesis of 2-Deoxy-β-Glycosides

  摘要：

  Novel bicyclic glycosyl donors have been prepared by the cycloaddition reaction of glycals with 3-thiono-2,4-pentanedione 17 followed by methylenation of the resulting ketone. Treatment of the heterocyclic donors with triflic acid in the presence of a variety of alcohol accepters leads to the formation of beta-glycosides in good yields and with excellent stereoselectivities. Desulfurization of the C-2 carbon-sulfur bonds gives the corresponding 2-deoxy-beta-glycosides. This method has been extended to the synthesis of glycosidic linkages found in the aureolic acid antibiotics. Tetra-N-butylammonium triflate proved to be a useful additive in these glycosylation reactions, suggesting an important role for triflate anion in stabilizing intermediates which are formed.

  DOI：

  10.1021/jo971934h
• 作为产物：
  描述：

  1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-α-D-glucopyranose 在 molecular sieve 、 三氟甲磺酸 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 4-methyl-3-[(2S,3R,4S,5R,6R)-2-naphthalen-2-yloxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]sulfanylpent-3-en-2-one
  参考文献：
  名称：

  A novel donor for the synthesis of 2-deoxy-β-glycosides

  摘要：

  Vinyl glycoside 2, available in two steps from tribenzyl glucal, is found to be an excellent glycosyl donor for the synthesis of 2-deoxy-beta-glycosides.

  DOI：

  10.1039/cc9960002651

文献信息

• A novel donor for the synthesis of 2-deoxy-β-glycosides
  作者：Cecilia H. Marzabadi、Richard W. Franck

  DOI：10.1039/cc9960002651

  日期：——

  Vinyl glycoside 2, available in two steps from tribenzyl glucal, is found to be an excellent glycosyl donor for the synthesis of 2-deoxy-beta-glycosides.
• Novel Bicylic Donors for the Synthesis of 2-Deoxy-β-Glycosides
  作者：Richard W. Franck、Cecilia H. Marzabadi

  DOI：10.1021/jo971934h

  日期：1998.4.1

  Novel bicyclic glycosyl donors have been prepared by the cycloaddition reaction of glycals with 3-thiono-2,4-pentanedione 17 followed by methylenation of the resulting ketone. Treatment of the heterocyclic donors with triflic acid in the presence of a variety of alcohol accepters leads to the formation of beta-glycosides in good yields and with excellent stereoselectivities. Desulfurization of the C-2 carbon-sulfur bonds gives the corresponding 2-deoxy-beta-glycosides. This method has been extended to the synthesis of glycosidic linkages found in the aureolic acid antibiotics. Tetra-N-butylammonium triflate proved to be a useful additive in these glycosylation reactions, suggesting an important role for triflate anion in stabilizing intermediates which are formed.