methyl 2,3,6-tri-O-benzyl-4-O-(methylsulfonyl)-α-D-galactopyranoside | 71454-40-5

• 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-(methylsulfonyl)-α-D-galactopyranoside
• 英文别名: Methyl 2,3,6-tri-O-benzyl-4-O-(methanesulfonyl)-α-D-galactopyranoside；Bn(-2)[Bn(-3)][Mes(-4)][Bn(-6)]a-Gal1Me；[(2R,3S,4R,5R,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl] methanesulfonate
• CAS: 71454-40-5
• 化学式: C₂₉H₃₄O₈S
• 分子量: 542.65
• InChiKey: DFOWDZCFMYGCIV-LLQHYSMESA-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

反应信息

• 作为反应物：
  描述：

  methyl 2,3,6-tri-O-benzyl-4-O-(methylsulfonyl)-α-D-galactopyranoside 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以84%的产率得到Methyl 4-azido-2,3,6-tri-O-benzyl-4-deoxy-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
• 作为产物：
  描述：

  methyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside 、 甲基磺酰氯 在 吡啶 作用下， 反应 6.0h， 以96%的产率得到methyl 2,3,6-tri-O-benzyl-4-O-(methylsulfonyl)-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

文献信息

• Synthesis of methyl 2,3-O-glycopyranosylidene-α-d-mannopyranosides having various substituents
  作者：Juji Yoshimura、Katsuji Asano、Kazuyuki Umemura、Shigeomi Horito、Hironobu Hashimoto

  DOI：10.1016/0008-6215(83)84016-6

  日期：1983.9

  title compounds were obtained by condensation of d -glucono-, d -galactono-, or l - glycero - d - gluco -heptono-1,5-lactones with methyl 2,3-di- O -(trimethylsilyl)-α- d -mannopyranosides having various substituents on C-4 and C-6, in the presence of trimethylsilyl trifluoromethanesulfonate as the catalyst. Except for a 6-acetoxyl group on a lactone component and a ( tert -butyldiphenylsiloxy) group

  摘要标题化合物是通过将d-葡萄糖酸-，d-半乳糖基-或l-甘油-d-葡萄糖-庚基-1,5-内酯与2,3-二甲基O-（三甲基甲硅烷基）-α缩合而获得的。在三甲基甲硅烷基三氟甲磺酸盐作为催化剂的存在下，在C-4和C-6上具有各种取代基的-d-甘露吡喃糖苷。除了内酯组分上的6-乙酰氧基和（叔丁基二苯基甲硅烷氧基）基团外，常用的C-取代基，例如苄氧基，烯丙氧基，叠氮基，酰氧基，（甲硫基）甲氧基和甲氧基，均不能阻止这种情况的发生。缩合。
• 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.