3,4-di-O-(carbonyl)-2,6-dideoxy-2-bromo-α-D-galactopyranosyl trichloroacetimidate | 548460-03-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 3,4-di-O-(carbonyl)-2,6-dideoxy-2-bromo-α-D-galactopyranosyl trichloroacetimidate
• 英文别名: [(3aS,4R,6R,7R,7aS)-7-bromo-4-methyl-2-oxo-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl] 2,2,2-trichloroethanimidate
• CAS: 548460-03-3
• 化学式: C₉H₉BrCl₃NO₅
• 分子量: 397.437
• InChiKey: VSDWEMNLFQPXJG-VFUOTHLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  77.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  acetyl 4-O-acetyl-6-deoxy-2-deoxy-2-iodo-D-glucopyranoside 、 3,4-di-O-(carbonyl)-2,6-dideoxy-2-bromo-α-D-galactopyranosyl trichloroacetimidate 在 tert-Butylsilyltrifluormethansulfonat 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到
  参考文献：
  名称：

  Recent advances in the synthesis of 2-deoxy-glycosides

  摘要：

  Glycosides of 2-deoxy-sugars, monosaccharides in which the hydroxyl group at C-2 is replaced with a hydrogen atom, occur widely in natural products and therefore have been the subject of intense synthetic activity. The report summarizes recent advances in this area, with a particular focus on work published since an earlier review on the topic, in 2000 (Marzabadi, C. H.: Franck, R. W. Tetrahedron 2000, 56, 8385-8417). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.07.013
• 作为产物：
  描述：

  3,4-di-O-(carbonyl)-6-deoxy-D-galactal 在 N-溴代丁二酰亚胺(NBS) 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.83h， 生成 3,4-di-O-(carbonyl)-2,6-dideoxy-2-bromo-α-D-galactopyranosyl trichloroacetimidate
  参考文献：
  名称：

  Stereoselective Synthesis of 2-Deoxy-β-Galactosides via 2-Deoxy-2-bromo- and 2-Deoxy-2-iodo-galactopyranosyl Donors

  摘要：

  A series of 2-bromo- and 2-iodo-galactopyranosyl acetates and trichloroacetimidates were evaluated as glycosyl donors for the synthesis of 2-deoxygalactopyranosides. The best selectivity for the beta-glycosidic linkage was achieved by using 6-deoxy-3,4-carbonate-protected galactosyl donors.

  DOI：

  10.1021/ol034393t

文献信息

• Stereoselective Synthesis of Functionalized Precursors of the CDEF and CDE 2,6-Dideoxy-tetra- and Trisaccharide Units of Durhamycins A and B
  作者：Timothy B. Durham、William R. Roush

  DOI：10.1021/ol034395d

  日期：2003.5.1

  [structure: see text] Highly stereoselective syntheses of functionalized precursors of the CDEF and CDE 2,6-dideoxy-tetra- and trisaccharide units of the anti-HIV aureolic acids durhamycins A and B using 2-deoxy-2-iodo- and 2-deoxy-2-bromopyranosyl donors are described.

  [结构：见正文]使用2-deoxy-2-iodo-和2的抗HIV金抗酸Durhamycins A和B的CDEF和CDE的功能化前体的2,6-二脱氧-四-和三糖单元的功能化前体的高度立体选择性合成描述了-脱氧-2-溴吡喃糖基供体。
• Recent advances in the synthesis of 2-deoxy-glycosides
  作者：Dianjie Hou、Todd L. Lowary

  DOI：10.1016/j.carres.2009.07.013

  日期：2009.10

  Glycosides of 2-deoxy-sugars, monosaccharides in which the hydroxyl group at C-2 is replaced with a hydrogen atom, occur widely in natural products and therefore have been the subject of intense synthetic activity. The report summarizes recent advances in this area, with a particular focus on work published since an earlier review on the topic, in 2000 (Marzabadi, C. H.: Franck, R. W. Tetrahedron 2000, 56, 8385-8417). (C) 2009 Elsevier Ltd. All rights reserved.
• Stereoselective Synthesis of 2-Deoxy-β-Galactosides via 2-Deoxy-2-bromo- and 2-Deoxy-2-iodo-galactopyranosyl Donors
  作者：Timothy B. Durham、William R. Roush

  DOI：10.1021/ol034393t

  日期：2003.5.1

  A series of 2-bromo- and 2-iodo-galactopyranosyl acetates and trichloroacetimidates were evaluated as glycosyl donors for the synthesis of 2-deoxygalactopyranosides. The best selectivity for the beta-glycosidic linkage was achieved by using 6-deoxy-3,4-carbonate-protected galactosyl donors.