2-Chloroethyl β-D-ribofuranoside | 64526-71-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Chloroethyl β-D-ribofuranoside
• 英文别名: 2-Chloraethyl-β-D-ribofuranosid；(2R,3R,4S,5R)-2-(2-chloroethoxy)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 64526-71-2；64949-99-1；64950-04-5
• 化学式: C₇H₁₃ClO₅
• 分子量: 212.63
• InChiKey: WJXMCOSDUFIENC-DBRKOABJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Chloroethyl β-D-ribofuranoside 在 咪唑 、 三氟化硼乙醚 、 sodium benzenesulfonate 、 4-甲基苯磺酸吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 potassium iodide 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 生成 10-[[(4S,5S,6R)-6-[[(3aR,4S,6R,6aR)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-2-(4-methoxyphenyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]oxymethyl]-5-hydroxy-2-(4-methoxyphenyl)-1,3-dioxan-4-yl]methyl]-7,8-dimethylbenzo[g]pteridine-2,4-dione
  参考文献：
  名称：

  Chemical synthesis of lampteroflavin as light emitter in the luminous mushroom, lampteromyces japonicus

  摘要：

  The synthesis of lampteroflavin (the light emitter of the luminous mushroom, Lampteromyces japonicus) is described. Protected riboflavin was stereoselectively glycosylated with ribofuranosyl imidate to give largely the alpha-product. Chloroethyl group which could be removed under neutral condition contributed to this synthesis.

  DOI：

  10.1016/s0040-4020(01)86553-4
• 作为产物：
  描述：

  1-乙酰氧基-2,3,5-三苯甲酰氧基-1-beta-D-呋喃核糖 在 氢氧化钾 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 15.0h， 生成 2-Chloroethyl β-D-ribofuranoside
  参考文献：
  名称：

  Chemical synthesis of lampteroflavin as light emitter in the luminous mushroom, lampteromyces japonicus

  摘要：

  The synthesis of lampteroflavin (the light emitter of the luminous mushroom, Lampteromyces japonicus) is described. Protected riboflavin was stereoselectively glycosylated with ribofuranosyl imidate to give largely the alpha-product. Chloroethyl group which could be removed under neutral condition contributed to this synthesis.

  DOI：

  10.1016/s0040-4020(01)86553-4

文献信息

• Direct Glycosylation of Unprotected and Unactivated Carbohydrates under Mild Conditions
  作者：Matthias Pfaffe、Rainer Mahrwald

  DOI：10.1021/ol203329u

  日期：2012.2.3

  Ligand exchange acetalization of acetals in the presence of catalytic amounts of mandelic acid and titanium tert-butoxide is reported. This transformation is successfully extended to glycosylation of unprotected and unactivated pentoses. Even unreactive pentoses such as d-arabinose or d-lyxose can be transformed by this new methodology into corresponding isopropyl glycosides.

  据报道，在催化量的扁桃酸和叔丁醇钛存在下，乙缩醛的配体交换缩醛化。该转化成功地扩展到未保护和未激活的戊糖的糖基化。甚至不反应的戊糖，例如d-阿拉伯糖或d- lyxose，也可以通过这种新方法转化为相应的异丙基糖苷。
• Organocatalyzed Direct Glycosylation of Unprotected and Unactivated Carbohydrates
  作者：Sebastian Schmalisch、Rainer Mahrwald

  DOI：10.1021/ol402914v

  日期：2013.11.15

  Organocatalyzed direct glycosylation of unprotected and unactivated carbohydrates is reported. This process is catalyzed by triphenylphosphine and tetrabromomethane at room temperature under neutral conditions. With this operationally simple protocol thermodynamically favored, glycosides were obtained in a very straightforward reaction.
• Lampteromyces bioluminescence — 5 chemical synthesis of lampteroflavin as mushroom light emitter
  作者：Minoru Isobe、Hiroyuki Takahashi、Toshio Goto

  DOI：10.1016/s0040-4039(00)94611-2

  日期：——
• ISOBE, MINORU;TAKAHASHI, HIROYUKI;GOTO, TOSHIO, TETRAHEDRON LETT., 31,(1990) N, C. 717-718
  作者：ISOBE, MINORU、TAKAHASHI, HIROYUKI、GOTO, TOSHIO

  DOI：——

  日期：——
• Chemical synthesis of lampteroflavin as light emitter in the luminous mushroom, lampteromyces japonicus
  作者：Hiroyuki Takahashi、Minoru Isobe、Toshio Goto

  DOI：10.1016/s0040-4020(01)86553-4

  日期：1991.8

  The synthesis of lampteroflavin (the light emitter of the luminous mushroom, Lampteromyces japonicus) is described. Protected riboflavin was stereoselectively glycosylated with ribofuranosyl imidate to give largely the alpha-product. Chloroethyl group which could be removed under neutral condition contributed to this synthesis.