(3R)-3-acetoxy-4-pentynyl 2',4'-O-bis(acetyl)-3',6'-O-bis(tert-butyldimethylsilyl)-β-D-glucopyranoside | 794521-06-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R)-3-acetoxy-4-pentynyl 2',4'-O-bis(acetyl)-3',6'-O-bis(tert-butyldimethylsilyl)-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-5-acetyloxy-6-[(3R)-3-acetyloxypent-4-ynoxy]-4-[tert-butyl(dimethyl)silyl]oxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]oxan-3-yl] acetate
• CAS: 794521-06-5
• 化学式: C₂₉H₅₂O₁₀Si₂
• 分子量: 616.897
• InChiKey: RZFASLNPLSTNDM-KPBLZALBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (3R)-3-acetoxy-4-pentynyl 2',4'-O-bis(acetyl)-3',6'-O-bis(tert-butyldimethylsilyl)-β-D-glucopyranoside 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 以63%的产率得到(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：

  (R)-5-(tert-butyldimethylsilanyloxy)pent-1-yn-3-ol 在 吡啶 、 4-二甲氨基吡啶 、 氟化氢吡啶 、 DMTST 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 (3R)-3-acetoxy-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