4-nitrophenyl 6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside | 157430-17-6

• 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: 4-nitrophenyl 6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• 英文别名: (2R,3S,6R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-(4-nitrophenoxy)-3,6-dihydro-2H-pyran-3-ol
• CAS: 157430-17-6
• 化学式: C₁₈H₂₇NO₆Si
• 分子量: 381.501
• InChiKey: BBHMXVJAKQVESQ-BBWFWOEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  93.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl 6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 sodium hydride 、 氯乙酸 、 三苯基膦 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 53.0h， 生成 4-nitrophenyl 4-O-(2'-bromoprop-2'-enyl)-6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-threo-hex-2-enopyranoside
  参考文献：
  名称：

  Palladium-Mediated Cyclization on Carbohydrate Templates. 3. Extension of The Cyclization to the Threo Series.

  摘要：

  The palladium(0)-catalyzed Heck-type cyclization-beta-alkoxy elimination reaction leading to enantiopure bicyclic compounds in the case of erythro 2,3-unsaturated glycosides has been successfully extended to the three stereoisomer by only changing the aglycon moiety from an ethoxy group to an aryloxy moiety.

  DOI：

  10.1080/07328300008544075
• 作为产物：
  描述：

  4-nitrophenyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 咪唑 、 sodium methylate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 4-nitrophenyl 6-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Palladium-Mediated Cyclization on Carbohydrate Templates. 3. Extension of The Cyclization to the Threo Series.

  摘要：

  The palladium(0)-catalyzed Heck-type cyclization-beta-alkoxy elimination reaction leading to enantiopure bicyclic compounds in the case of erythro 2,3-unsaturated glycosides has been successfully extended to the three stereoisomer by only changing the aglycon moiety from an ethoxy group to an aryloxy moiety.

  DOI：

  10.1080/07328300008544075

文献信息

• Palladium-Mediated Cyclization on Carbohydrate Templates. 3. Extension of The Cyclization to the Threo Series.
  作者：Karim Bedjeguelal、Laure Joseph、Véronique Bolitt、Denis Sinou

  DOI：10.1080/07328300008544075

  日期：2000.1

  The palladium(0)-catalyzed Heck-type cyclization-beta-alkoxy elimination reaction leading to enantiopure bicyclic compounds in the case of erythro 2,3-unsaturated glycosides has been successfully extended to the three stereoisomer by only changing the aglycon moiety from an ethoxy group to an aryloxy moiety.