Methyl 2,3,6-tri-O-benzyl-4-O-(methanesulfonyl)-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 2,3,6-tri-O-benzyl-4-O-(methanesulfonyl)-α-D-glucopyranoside
• 英文别名: Bn(-2)[Bn(-3)][Mes(-4)][Bn(-6)]a-Glc1Me；[(2R,3R,4R,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl] methanesulfonate
• 化学式: C₂₉H₃₄O₈S
• 分子量: 542.65
• InChiKey: DFOWDZCFMYGCIV-RQKPWJHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  8

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷	methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside	19488-48-3	C28H32O6	464.558

反应信息

• 作为反应物：
  描述：

  Methyl 2,3,6-tri-O-benzyl-4-O-(methanesulfonyl)-α-D-glucopyranoside 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以76%的产率得到Methyl 4-azido-2,3,6-tri-O-benzyl-4-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Syntheses of Trehazolin Derivatives and Evaluation as Glycosidase Inhibitors

  摘要：

  The trehazolin derivatives 9-12 were synthesized from the aminocyclitol (7), which is the degradation product of trehazolin (5). In particular, compounds 9-11 were pseudodisaccharides that underwent replacement of the corresponding nonreducing D-glucose moieties of isomaltose and maltose by trehalamine (6), and they were designed to be therapeutic drugs; however, they did not show significant activities.

  DOI：

  10.1021/jo00113a041
• 作为产物：
  描述：

  甲基2,3,6-三-O-苄基-ALPHA-D-吡喃葡萄糖苷 、 甲基磺酰氯 在 吡啶 作用下， 反应 5.0h， 以95%的产率得到Methyl 2,3,6-tri-O-benzyl-4-O-(methanesulfonyl)-α-D-glucopyranoside
  参考文献：
  名称：

  Syntheses of Trehazolin Derivatives and Evaluation as Glycosidase Inhibitors

  摘要：

  The trehazolin derivatives 9-12 were synthesized from the aminocyclitol (7), which is the degradation product of trehazolin (5). In particular, compounds 9-11 were pseudodisaccharides that underwent replacement of the corresponding nonreducing D-glucose moieties of isomaltose and maltose by trehalamine (6), and they were designed to be therapeutic drugs; however, they did not show significant activities.

  DOI：

  10.1021/jo00113a041

文献信息

• Syntheses of Trehazolin Derivatives and Evaluation as Glycosidase Inhibitors
  作者：Yoshiyuki Kobayashi、Masao Shiozaki、Osamu Ando

  DOI：10.1021/jo00113a041

  日期：1995.4

  The trehazolin derivatives 9-12 were synthesized from the aminocyclitol (7), which is the degradation product of trehazolin (5). In particular, compounds 9-11 were pseudodisaccharides that underwent replacement of the corresponding nonreducing D-glucose moieties of isomaltose and maltose by trehalamine (6), and they were designed to be therapeutic drugs; however, they did not show significant activities.