(4aR,6R,7R,8S,8aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-isopropenyl-3-methyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene | 185836-58-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4aR,6R,7R,8S,8aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-isopropenyl-3-methyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene
• 英文别名: (4aR,6R,7R,8S,8aR)-3-methyl-7,8-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-prop-1-en-2-yl-6,7,8,8a-tetrahydro-4aH-pyrano[2,3-b][1,4]oxathiine
• CAS: 185836-58-2
• 化学式: C₃₃H₃₆O₅S
• 分子量: 544.712
• InChiKey: HKQQAWMWVSFGAX-FRUKUSMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4aR,6R,7R,8S,8aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-isopropenyl-3-methyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene 在 三氟甲磺酸 、 3 A molecular sieve 、 镍 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 1.5h， 生成 methyl 3,4,6-tri-O-benzyl-2-deoxy-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 、 alkaline earth salt of/the/ methylsulfuric acid 在 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 以76%的产率得到(4aR,6R,7R,8S,8aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-isopropenyl-3-methyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene
  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

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.