5-azido-3,6-di-O-benzyl-5-deoxy-D-gulono-1,4-lactone | 1395068-34-4

• 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: 5-azido-3,6-di-O-benzyl-5-deoxy-D-gulono-1,4-lactone
• 英文别名: (3R,4S,5S)-5-[(1R)-1-azido-2-phenylmethoxyethyl]-3-hydroxy-4-phenylmethoxyoxolan-2-one
• CAS: 1395068-34-4
• 化学式: C₂₀H₂₁N₃O₅
• 分子量: 383.404
• InChiKey: NONHJUCMCWXKTR-YRXWBPOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-azido-3,6-di-O-benzyl-5-deoxy-D-gulono-1,4-lactone 在 吡啶 、 甲胺 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 2.0h， 生成 methyl 5-azido-3,6-di-O-benzyl-5-deoxy-2-O-methanesulfonyl-D-idonamide
  参考文献：
  名称：

  Nine of 16 Stereoisomeric Polyhydroxylated Proline Amides Are Potent β-N-Acetylhexosaminidase Inhibitors

  摘要：

  All 16 stereoisomeric N-methyl 5-(hydroxymethyl)-3,4-dihydroxyproline amides have been synthesized from lactones accessible from the enantiomers of glucuronolactone. Nine stereoisomers, including all eight with a (3R)-hydroxyl configuration, are low to submicromolar inhibitors of beta-N-acetylhexosaminidases. A structural correlation between the proline amides is found with the ADMDP-acetamide analogues bearing an acetamidomethylpyrrolidine motif. The proline amides are generally more potent than their ADMDP-acetamide equivalents. beta-N-Acetylhexosaminidase inhibition by an azetidine ADMDP-acetamide analogue is compared to an azetidine carboxylic acid amide. None of the amides are good alpha-N-acetylgalactosaminidase inhibitors.

  DOI：

  10.1021/jo500157p
• 作为产物：
  描述：

  (3aS,5S,6R,6aS)-5-[(1R)-1-azido-2-phenylmethoxyethyl]-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole 在 吡啶 、 碘 、 sodium 2,2,2-trifluoroacetate 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 7.5h， 生成 5-azido-3,6-di-O-benzyl-5-deoxy-D-gulono-1,4-lactone
  参考文献：
  名称：

  由葡糖醛酸内酯对映异构体制备的所有10种立体异构体2,5-二脱氧-2,5-亚氨基己糖醇对糖苷酶的抑制作用

  摘要：

  葡糖醛酸内酯的对映体是用于合成10个立体异构体2,5-二脱氧-2,5-亚氨基己糖醇的优秀的Chirons，通过在C2和C5处进行氮取代形成吡咯烷环，而保留或反转构型。在合成过程中，可以调节C3处的立体化学，以从每种对映异构体中产生7种立体异构体。对一组13种糖苷酶的糖苷酶抑制作用的确定性并排比较显示，这10种立体异构体中有8种对至少一种糖苷酶具有明显的抑制作用。

  DOI：

  10.1021/jo301243s

文献信息

• Nine of 16 Stereoisomeric Polyhydroxylated Proline Amides Are Potent β-<i>N</i>-Acetylhexosaminidase Inhibitors
  作者：Benjamin J. Ayers、Andreas F. G. Glawar、R. Fernando Martínez、Nigel Ngo、Zilei Liu、George W. J. Fleet、Terry D. Butters、Robert J. Nash、Chu-Yi Yu、Mark R. Wormald、Shinpei Nakagawa、Isao Adachi、Atsushi Kato、Sarah F. Jenkinson

  DOI：10.1021/jo500157p

  日期：2014.4.18

  All 16 stereoisomeric N-methyl 5-(hydroxymethyl)-3,4-dihydroxyproline amides have been synthesized from lactones accessible from the enantiomers of glucuronolactone. Nine stereoisomers, including all eight with a (3R)-hydroxyl configuration, are low to submicromolar inhibitors of beta-N-acetylhexosaminidases. A structural correlation between the proline amides is found with the ADMDP-acetamide analogues bearing an acetamidomethylpyrrolidine motif. The proline amides are generally more potent than their ADMDP-acetamide equivalents. beta-N-Acetylhexosaminidase inhibition by an azetidine ADMDP-acetamide analogue is compared to an azetidine carboxylic acid amide. None of the amides are good alpha-N-acetylgalactosaminidase inhibitors.
• Glycosidase Inhibition by All 10 Stereoisomeric 2,5-Dideoxy-2,5-iminohexitols Prepared from the Enantiomers of Glucuronolactone
  作者：Benjamin J. Ayers、Nigel Ngo、Sarah F. Jenkinson、R. Fernando Martínez、Yousuke Shimada、Isao Adachi、Alexander C. Weymouth-Wilson、Atsushi Kato、George W. J. Fleet

  DOI：10.1021/jo301243s

  日期：2012.9.21

  glucuronolactone are excellent chirons for the synthesis of the 10 stereoisomeric 2,5-dideoxy-2,5-iminohexitols by formation of the pyrrolidine ring by nitrogen substitution at C2 and C5, with either retention or inversion of configuration; the stereochemistry at C3 may be adjusted during the synthesis to give seven stereoisomers from each enantiomer. A definitive side-by-side comparison of the glycosidase

  葡糖醛酸内酯的对映体是用于合成10个立体异构体2,5-二脱氧-2,5-亚氨基己糖醇的优秀的Chirons，通过在C2和C5处进行氮取代形成吡咯烷环，而保留或反转构型。在合成过程中，可以调节C3处的立体化学，以从每种对映异构体中产生7种立体异构体。对一组13种糖苷酶的糖苷酶抑制作用的确定性并排比较显示，这10种立体异构体中有8种对至少一种糖苷酶具有明显的抑制作用。