(E)-3-[(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-hydroxymethyl-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy)-tetrahydro-pyran-2-yl]-acrylic acid methyl ester | 197007-68-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-3-[(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-hydroxymethyl-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy)-tetrahydro-pyran-2-yl]-acrylic acid methyl ester
• CAS: 197007-68-4
• 化学式: C₅₂H₅₈O₁₃
• 分子量: 891.025
• InChiKey: VEBQOCURQBEHPY-KPEWAIHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.09
• 重原子数：
  65.0
• 可旋转键数：
  24.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  138.83
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  (E)-3-[(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-hydroxymethyl-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy)-tetrahydro-pyran-2-yl]-acrylic acid methyl ester 在 四氧化锇 、 N-甲基吲哚酮 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 48.0h， 生成 (2S,3R)-2,3-Diacetoxy-3-[(2S,3S,4S,5R,6R)-6-((2S,3S,4R,5R)-5-acetoxymethyl-3,4-bis-benzyloxy-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy)-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yl]-propionic acid methyl ester
  参考文献：
  名称：

  Higher Sucrose Analogs: Homologation of a Glucose Unit of Sucrose by Two Carbon Atoms

  摘要：

  The primary hydroxyl groups (at C-6 and C-6') in 2,3,4,3'4'-penta-O-benzyl-1'-O-methoxymethyl sucrose (2) can be reactively differentiated with tert-butyldiphenylsilyl chloride. Reaction of 2 with TBDPSCl afforded only one monosilylated product protected at C-6' (6). The regioisomeric monoprotected sucrose 8 was prepared by selective deprotection of the double silylated derivative 7. Compound 6 was converted into 2,3,4,3',4'-penta-O-benzyl-6-carbomethoxymethylidene-1'-O-methoxymethylsucrose 10 in three steps. Osmylation of the double bond in 10 afforded stereoisomeric homologated sucroses: 11a [6(S),7(R)] and 11b [6(R),7(S)] in the ratio 3:2. A large downfield shift of the H-1 (up to 0.5 ppm) was observed for 6'-silylated derivatives.

  DOI：

  10.1080/07328309708005741
• 作为产物：
  描述：

  1'-O-methoxymethyl-2,3,4,3',4'-penta-O-benzyl-sucrose 在 4-二甲氨基吡啶 、 草酰氯 、 四丁基氟化铵 、 二甲基亚砜 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 95.25h， 生成 (E)-3-[(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-((2S,3S,4R,5R)-3,4-bis-benzyloxy-5-hydroxymethyl-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy)-tetrahydro-pyran-2-yl]-acrylic acid methyl ester
  参考文献：
  名称：

  Higher Sucrose Analogs: Homologation of a Glucose Unit of Sucrose by Two Carbon Atoms

  摘要：

  The primary hydroxyl groups (at C-6 and C-6') in 2,3,4,3'4'-penta-O-benzyl-1'-O-methoxymethyl sucrose (2) can be reactively differentiated with tert-butyldiphenylsilyl chloride. Reaction of 2 with TBDPSCl afforded only one monosilylated product protected at C-6' (6). The regioisomeric monoprotected sucrose 8 was prepared by selective deprotection of the double silylated derivative 7. Compound 6 was converted into 2,3,4,3',4'-penta-O-benzyl-6-carbomethoxymethylidene-1'-O-methoxymethylsucrose 10 in three steps. Osmylation of the double bond in 10 afforded stereoisomeric homologated sucroses: 11a [6(S),7(R)] and 11b [6(R),7(S)] in the ratio 3:2. A large downfield shift of the H-1 (up to 0.5 ppm) was observed for 6'-silylated derivatives.

  DOI：

  10.1080/07328309708005741