(1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-(4-bromobenzyl)-4-methylphenyl]-1-thio-D-glucitol | 1000369-06-1

• 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: (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-(4-bromobenzyl)-4-methylphenyl]-1-thio-D-glucitol
• 英文别名: (2S,3R,4R,5S,6R)-2-[5-[(4-bromophenyl)methyl]-4-methyl-2-phenylmethoxyphenyl]-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)thiane
• CAS: 1000369-06-1
• 化学式: C₅₅H₅₃BrO₅S
• 分子量: 905.993
• InChiKey: NVOLUWHEHOJWKG-UZQUDJGMSA-N

物化性质

• 沸点：
  906.7±65.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.3
• 重原子数：
  62
• 可旋转键数：
  19
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-(4-bromobenzyl)-4-methylphenyl]-1-thio-D-glucitol 在 palladium diacetate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 乙醇 、 氯仿 、 乙腈 为溶剂， 生成 (1S)-1,5-anhydro-1-{2-hydroxy-5-[4-(4-{[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]amino}-4-oxobutyl)benzyl]-4-methylphenyl}-1-thio-D-glucitol
  参考文献：
  名称：

  Discovery of a potent, low-absorbable sodium-dependent glucose cotransporter 1 (SGLT1) inhibitor (TP0438836) for the treatment of type 2 diabetes

  摘要：

  The design and synthesis of a novel class of low-absorbable SGLT1 inhibitors are described. To achieve low absorption in the new series, we performed an optimization study based on a strategy to increase TPSA. Fortunately, the optimization of an aglycon moiety and a side chain of the distal aglycon moiety led to the identification of compound 30b as a potent and low-absorbable SGLT1 inhibitor. Compound 30b showed a desirable PK profile in Sprague-Dawley (SD) rats and a favorable glucose-lowering effect in diabetic rats.

  DOI：

  10.1016/j.bmcl.2018.09.035
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-1-C-[2-(benzyloxy)-5-formyl-4-methylphenyl]-5-thio-D-glucopyranose 在 三乙基硅烷 、 正丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 氯仿 、 乙腈 为溶剂， 生成 (1S)-1,5-anhydro-2,3,4,6-tetra-O-benzyl-1-[2-(benzyloxy)-5-(4-bromobenzyl)-4-methylphenyl]-1-thio-D-glucitol
  参考文献：
  名称：

  Discovery of a potent, low-absorbable sodium-dependent glucose cotransporter 1 (SGLT1) inhibitor (TP0438836) for the treatment of type 2 diabetes

  摘要：

  The design and synthesis of a novel class of low-absorbable SGLT1 inhibitors are described. To achieve low absorption in the new series, we performed an optimization study based on a strategy to increase TPSA. Fortunately, the optimization of an aglycon moiety and a side chain of the distal aglycon moiety led to the identification of compound 30b as a potent and low-absorbable SGLT1 inhibitor. Compound 30b showed a desirable PK profile in Sprague-Dawley (SD) rats and a favorable glucose-lowering effect in diabetic rats.

  DOI：

  10.1016/j.bmcl.2018.09.035

文献信息

• C-PHENYL 1-THIOGLUCITOL COMPOUND
  申请人：TAISHO PHARMACEUTICAL CO., LTD

  公开号：EP2036901B1

  公开（公告）日：2013-05-01
• US8115017B2
  申请人：——

  公开号：US8115017B2

  公开（公告）日：2012-02-14