isopropyl 4-O-acetyl-2,3,6-trideoxy-L-erythro-hex-2-enopyranoside | 952498-14-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: isopropyl 4-O-acetyl-2,3,6-trideoxy-L-erythro-hex-2-enopyranoside
• 英文别名: [(2S,3R)-2-methyl-6-propan-2-yloxy-3,6-dihydro-2H-pyran-3-yl] acetate
• CAS: 952498-14-5
• 化学式: C₁₁H₁₈O₄
• 分子量: 214.262
• InChiKey: GNICOSFGLCYSEQ-OZRKRLJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  isopropyl 4-O-acetyl-2,3,6-trideoxy-L-erythro-hex-2-enopyranoside 在 palladium on activated charcoal 、 二苯基膦叠氮化物 氢气 、 potassium carbonate 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、206.85 kPa 条件下， 反应 30.0h， 生成 isopropyl 4-azido-4-deoxy-β-L-amicetoside
  参考文献：
  名称：

  A divergent strategy for constructing a sugar library containing 2,6-dideoxy sugars and uncommon sugars with 4-substitution

  摘要：

  A practical strategy has been developed for delivering 2,6-dideoxy sugars and uncommon sugars with 4-substitution. This strategy employed Ferrier rearrangement reaction and BF3 center dot OEt2-induced peroxidation to construct key intermediates 2,3-unsaturated glycosides and alpha,beta-unsaturated lactones from peracetyl rhamnal. After further derivatization, four uncommon sugars with 4-substitution and eight uncommon sugar units with 3,4-disubstitution were successfully synthesized. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.019
• 作为产物：
  描述：

  异丙醇 、 3,4-二-O-乙酰-1,5-酐-2,6-双脱氧-L-阿拉伯-己-1-糖醇 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以80%的产率得到isopropyl 4-O-acetyl-2,3,6-trideoxy-L-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  A divergent strategy for constructing a sugar library containing 2,6-dideoxy sugars and uncommon sugars with 4-substitution

  摘要：

  A practical strategy has been developed for delivering 2,6-dideoxy sugars and uncommon sugars with 4-substitution. This strategy employed Ferrier rearrangement reaction and BF3 center dot OEt2-induced peroxidation to construct key intermediates 2,3-unsaturated glycosides and alpha,beta-unsaturated lactones from peracetyl rhamnal. After further derivatization, four uncommon sugars with 4-substitution and eight uncommon sugar units with 3,4-disubstitution were successfully synthesized. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.019

文献信息

• Glycosidation of glycals by 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) as a catalytic promoter
  作者：Kazunobu Toshima、Toru Ishizuka、Goh Matsuo、Masaya Nakata、Mitsuhiro Kinoshita

  DOI：10.1039/c39930000704

  日期：——

  O-Glycosidations of glycals 1, 8 and 9 with several alcohols by using a catalytic amount of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) under neutral conditions proceeds smoothly to give the corresponding 2,3-unsaturated glycosides in high yields.

  在中性条件下，使用一定量的 2,3-二氯-5,6-二氰基对苯醌（DDQ）催化剂，将甘油 1、8 和 9 与几种醇进行 O-糖苷化反应，反应进展顺利，并以高产率得到相应的 2,3-不饱和糖苷。
• InBr3-catalyzed cyclization of glycosides with arylamines
  作者：Pingyuan Wang、Meining Wang、Xuefeng Zhang、Guangfu Yang、Ao Zhang

  DOI：10.1016/j.tet.2012.04.116

  日期：2012.7

  Glycals have served as excellent substrates in the glycosidation reactions with arylamines to construct both C-C and C-N linkages simultaneously. However, the high reactivity and moisture/alcohol-sensitivity is also responsible for several side reactions. Herein we reported that 2,3-unsaturated glycosides can be used as alternatives of glycals to take part in the corresponding glycosidation as well. Therefore, with 10% of InBr3 or InI3 as the catalyst, 2,3-unsaturated glycosides containing various C-1 alkoxy groups reacted with arylamines smoothly and produced the glycosidation products in moderate to good yields as a pair of diastereomers with variant diastereoselectivity. (c) 2012 Elsevier Ltd. All rights reserved.