(Methyl 2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranosid-4-yl) isothiocyanate | 140934-01-6

• 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: (Methyl 2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranosid-4-yl) isothiocyanate
• 英文别名: (2S,3R,4S,5R,6S)-5-isothiocyanato-2-methoxy-3,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 140934-01-6
• 化学式: C₂₉H₃₁NO₅S
• 分子量: 505.635
• InChiKey: QOEJYBNAUFZHQX-RQKPWJHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  DL-(1,3/2,4,5)-5-amino-1-C-(hydroxymethyl)cyclopentane-1,2,3,4-tetraol 、 (Methyl 2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranosid-4-yl) isothiocyanate 以 四氢呋喃 、 水 为溶剂， 反应 144.0h， 以94%的产率得到N-(Methyl 2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranosid-4-yl)-N'-<<(1R)-(1α,2β,3α,4β,5β)>-1-(hydroxymethyl)-1,2,3,4-tetrahydroxycyclopent-5-yl>thiourea
  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：

  二硫化碳 、 Methyl 2,3,6-tri-O-benzyl-4-deoxy-4-(diethylphosphoramido)-α-D-glucopyranoside 在 四丁基溴化铵 、 sodium hydride 作用下， 以 苯 为溶剂， 以91%的产率得到(Methyl 2,3,6-tri-O-benzyl-4-deoxy-α-D-glucopyranosid-4-yl) isothiocyanate
  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

• Knapp; Purandare; Rupitz, Journal of the American Chemical Society, 1994, vol. 116, # 16, p. 7461 - 7462
  作者：Knapp、Purandare、Rupitz、Withers

  DOI：——

  日期：——
• 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.