{(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[(2S,3S,4R,5R)-3,4-bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy]-tetrahydro-pyran-2-yl}-methanol | 197007-59-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: {(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[(2S,3S,4R,5R)-3,4-bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy]-tetrahydro-pyran-2-yl}-methanol
• CAS: 197007-59-3
• 化学式: C₆₅H₇₄O₁₂Si
• 分子量: 1075.38
• InChiKey: VJVGAOKGYBVWFT-OSROZRSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.94
• 重原子数：
  78.0
• 可旋转键数：
  27.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  121.76
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  {(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[(2S,3S,4R,5R)-3,4-bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy]-tetrahydro-pyran-2-yl}-methanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 (2S,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-[(2S,3S,4R,5R)-3,4-bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy]-tetrahydro-pyran-2-carbaldehyde
  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：

  叔丁基二苯基氯硅烷 、 1'-O-methoxymethyl-2,3,4,3',4'-penta-O-benzyl-sucrose 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以15%的产率得到(2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-[(2S,3S,4R,5R)-3,4-bis-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-methoxymethoxymethyl-tetrahydro-furan-2-yloxy]-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran
  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