p-tolyl 2,3,4-O-tris(acetyl)-6-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside | 794521-01-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 2,3,4-O-tris(acetyl)-6-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside
• 英文别名: 1-S-tolyl-2,3,4-tri-OAcetyl-6-O-tertbutyldimethylsilyl-alpha-D-Glucopyranoside；[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-(4-methylphenyl)sulfanyloxan-3-yl] acetate
• CAS: 794521-01-0
• 化学式: C₂₅H₃₈O₈SSi
• 分子量: 526.723
• InChiKey: VFXGGUXWIDLFGL-SJSRKZJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  123
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (3R)-3-acetoxy-4-pentyn-1-ol 、 p-tolyl 2,3,4-O-tris(acetyl)-6-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside 在 DMTST 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以74%的产率得到[(3aR,5R,6R,7S,7aR)-7-acetyloxy-2-[(3R)-3-acetyloxypent-4-ynoxy]-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-methyl-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-6-yl] acetate
  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 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 p-tolyl 2,3,4-O-tris(acetyl)-6-O-(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