p-tolyl 3,6-O-bis(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside | 794521-00-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 3,6-O-bis(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5R,6S)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-(4-methylphenyl)sulfanyloxane-3,5-diol
• CAS: 794521-00-9
• 化学式: C₂₅H₄₆O₅SSi₂
• 分子量: 514.874
• InChiKey: JJZJUWUVCKRBNT-CCSDVLNMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.95
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  93.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-tolyl 3,6-O-bis(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 、 DMTST 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.5h， 生成 (3'R)-3'-acetoxy-5'-bromo-4'-pentynyl 2,4-O-bis(acetyl)-3,6-O-bis(tert-butyldimethylsilyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Total synthesis of bidensyneosides A2 and C: remarkable protecting group effects in glycosylation

  摘要：

  Bidensyneosides are a group of five recently identified polyacetylenic glucosides from Bidens parviflora WILLD, a traditional Chinese medicinal plant that contains rich bioactive natural products. It was shown that bidensyneosides inhibited both histamine release and nitric oxide production. The synthesis of bidensyneoside A2 (2) and C (4) as well as 3-deoxybidensyneoside C (5) are described. These syntheses establish a synthetic entry to the bidensyneosides and confirm the stereochemistry at C3. Furthermore, a remarkable protecting Group effect on orthoester formation was observed during the glycosylation reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.012
• 作为产物：
  描述：

  p-tolyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 在 咪唑 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 p-tolyl 3,6-O-bis(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Total synthesis of bidensyneosides A2 and C: remarkable protecting group effects in glycosylation

  摘要：

  Bidensyneosides are a group of five recently identified polyacetylenic glucosides from Bidens parviflora WILLD, a traditional Chinese medicinal plant that contains rich bioactive natural products. It was shown that bidensyneosides inhibited both histamine release and nitric oxide production. The synthesis of bidensyneoside A2 (2) and C (4) as well as 3-deoxybidensyneoside C (5) are described. These syntheses establish a synthetic entry to the bidensyneosides and confirm the stereochemistry at C3. Furthermore, a remarkable protecting Group effect on orthoester formation was observed during the glycosylation reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.08.012

文献信息

• Total synthesis of bidensyneosides A2 and C: remarkable protecting group effects in glycosylation
  作者：Benjamin W. Gung、Ryan M. Fox

  DOI：10.1016/j.tet.2004.08.012

  日期：2004.10

  Bidensyneosides are a group of five recently identified polyacetylenic glucosides from Bidens parviflora WILLD, a traditional Chinese medicinal plant that contains rich bioactive natural products. It was shown that bidensyneosides inhibited both histamine release and nitric oxide production. The synthesis of bidensyneoside A2 (2) and C (4) as well as 3-deoxybidensyneoside C (5) are described. These syntheses establish a synthetic entry to the bidensyneosides and confirm the stereochemistry at C3. Furthermore, a remarkable protecting Group effect on orthoester formation was observed during the glycosylation reaction. (C) 2004 Elsevier Ltd. All rights reserved.