5-(3-chlorobenzyl)-1,3,4-thiadiazol-2-yl 1-thio-β-D-glucopyranoside | 1231980-88-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(3-chlorobenzyl)-1,3,4-thiadiazol-2-yl 1-thio-β-D-glucopyranoside
• 英文别名: (2S,3R,4S,5S,6R)-2-[[5-[(3-chlorophenyl)methyl]-1,3,4-thiadiazol-2-yl]sulfanyl]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1231980-88-3
• 化学式: C₁₅H₁₇ClN₂O₅S₂
• 分子量: 404.895
• InChiKey: KMAGTRZEWHEQEX-LPUQOGTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  170
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5-(3-chlorobenzyl)-1,3,4-thiadiazol-2-yl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以83%的产率得到5-(3-chlorobenzyl)-1,3,4-thiadiazol-2-yl 1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Thiadiazole-based Thioglycosides as Sodium-glucose Co-transporter 2 (SGLT2) Inhibitors

  摘要：

  AbstractA series of thiadiazole‐based thioglycosides were synthesized as SGLT2 inhibitors from D‐glucose, D‐galactose and a variety of phenylacetic acids via a convenient protocol in 8 steps and evaluated in vivo with an oral glucose tolerance test (OGTT), and 5‐benzyl‐1,3,4‐thiadiazol‐2‐yl 1‐thio‐β‐D‐glucopyranoside (1a) was the most efficacious to suppress the blood glucose excursion during OGTT.

  DOI：

  10.1002/cjoc.201090120

文献信息

• Thiadiazole-based Thioglycosides as Sodium-glucose Co-transporter 2 (SGLT2) Inhibitors
  作者：Yunlong Gao、Guilong Zhao、Wei Liu、Yuli Wang、Weiren Xu、Jianwu Wang

  DOI：10.1002/cjoc.201090120

  日期：——

  AbstractA series of thiadiazole‐based thioglycosides were synthesized as SGLT2 inhibitors from D‐glucose, D‐galactose and a variety of phenylacetic acids via a convenient protocol in 8 steps and evaluated in vivo with an oral glucose tolerance test (OGTT), and 5‐benzyl‐1,3,4‐thiadiazol‐2‐yl 1‐thio‐β‐D‐glucopyranoside (1a) was the most efficacious to suppress the blood glucose excursion during OGTT.