benzyl β-D-4-O-methanesulfonyl-2,3-dideoxypent-2-enoglyceropyranoside | 405145-91-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: benzyl β-D-4-O-methanesulfonyl-2,3-dideoxypent-2-enoglyceropyranoside
• 英文别名: [(3S,6R)-6-phenylmethoxy-3,6-dihydro-2H-pyran-3-yl] methanesulfonate
• CAS: 405145-91-7
• 化学式: C₁₃H₁₆O₅S
• 分子量: 284.333
• InChiKey: QYCNLFLQOAMJOM-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  benzyl β-D-4-O-methanesulfonyl-2,3-dideoxypent-2-enoglyceropyranoside 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 Amberlite IRA-900 in azide form 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 、 苯 为溶剂， 反应 5.0h， 生成 benzyl β-L-4-methoxycarbonylacetamido-2,3,4-trideoxypent-2-enoglyceropyranoside
  参考文献：
  名称：

  Steric constraints against [3,3]-sigmatropic rearrangement of allylic azides. A convenient approach to β-l-4-aminopent-2-enoglyceropyranosides

  摘要：

  Starting from alkyl alpha -D-4-O-methanesulphonylpent-2-enoglyceropyranosides 13a-c, nucleophilic substitution carried out with polymer-supported azide ion led to regioisomeric mixtures of the azides 14a-c and 15a-c. An analogous result, due to a [3,3]-sigmatropic rearrangement, was observed starting from methyl alpha -D-hex-2-enoerythropyranoside derivatives 6a and 6b. On the contrary, starting from alkyl beta -D-4-O-methanesulphonylpent-2-enoglyceropyranosides 21a-c, azides 22a-c were exclusively obtained. and subsequently converted into the corresponding amino derivatives 23a-c. The behaviour of P-anomers 21a-c was ascribed to steric interactions in the cyclic transition state, as supported by ab initio calculations. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00450-5
• 作为产物：
  描述：

  benzyl β-D-4-O-acetyl-2,3-dideoxypent-2-enoglyceropyranoside 在 4-二甲氨基吡啶 、 resin IRA 900 in the methoxide form 、 三乙胺 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 benzyl β-D-4-O-methanesulfonyl-2,3-dideoxypent-2-enoglyceropyranoside
  参考文献：
  名称：

  Steric constraints against [3,3]-sigmatropic rearrangement of allylic azides. A convenient approach to β-l-4-aminopent-2-enoglyceropyranosides

  摘要：

  Starting from alkyl alpha -D-4-O-methanesulphonylpent-2-enoglyceropyranosides 13a-c, nucleophilic substitution carried out with polymer-supported azide ion led to regioisomeric mixtures of the azides 14a-c and 15a-c. An analogous result, due to a [3,3]-sigmatropic rearrangement, was observed starting from methyl alpha -D-hex-2-enoerythropyranoside derivatives 6a and 6b. On the contrary, starting from alkyl beta -D-4-O-methanesulphonylpent-2-enoglyceropyranosides 21a-c, azides 22a-c were exclusively obtained. and subsequently converted into the corresponding amino derivatives 23a-c. The behaviour of P-anomers 21a-c was ascribed to steric interactions in the cyclic transition state, as supported by ab initio calculations. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00450-5

文献信息

• Steric constraints against [3,3]-sigmatropic rearrangement of allylic azides. A convenient approach to β-l-4-aminopent-2-enoglyceropyranosides
  作者：Cristiana Fava、Roberta Galeazzi、Giovanna Mobbili、Mario Orena

  DOI：10.1016/s0957-4166(01)00450-5

  日期：2001.10

  Starting from alkyl alpha -D-4-O-methanesulphonylpent-2-enoglyceropyranosides 13a-c, nucleophilic substitution carried out with polymer-supported azide ion led to regioisomeric mixtures of the azides 14a-c and 15a-c. An analogous result, due to a [3,3]-sigmatropic rearrangement, was observed starting from methyl alpha -D-hex-2-enoerythropyranoside derivatives 6a and 6b. On the contrary, starting from alkyl beta -D-4-O-methanesulphonylpent-2-enoglyceropyranosides 21a-c, azides 22a-c were exclusively obtained. and subsequently converted into the corresponding amino derivatives 23a-c. The behaviour of P-anomers 21a-c was ascribed to steric interactions in the cyclic transition state, as supported by ab initio calculations. (C) 2001 Elsevier Science Ltd. All rights reserved.