[10-tert-butyldimethylsilyloxy-8-decene-4,6-diynyl]-β-D-glucopyranoside | 794520-92-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: [10-tert-butyldimethylsilyloxy-8-decene-4,6-diynyl]-β-D-glucopyranoside
• 英文别名: (2R,3R,4S,5S,6R)-2-[(E)-10-[tert-butyl(dimethyl)silyl]oxydec-8-en-4,6-diynoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 794520-92-6
• 化学式: C₂₂H₃₆O₇Si
• 分子量: 440.609
• InChiKey: JHXVTXWOQVFTNC-GKPWWNHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  109
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [10-tert-butyldimethylsilyloxy-8-decene-4,6-diynyl]-β-D-glucopyranoside 在 氟化氢吡啶 作用下， 以 四氢呋喃 为溶剂， 以51%的产率得到3-deoxybidensyneoside C
  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：

  1,2,3,4,6-alpha-D-葡萄糖五乙酸酯 在 三氟化硼乙醚 、 盐酸羟胺 、 乙胺 、 copper(l) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 [10-tert-butyldimethylsilyloxy-8-decene-4,6-diynyl]-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.