(2R,6R)-2-chloro-4-benzoyloxy-6-methyl-2H-pyran-3-(6H)-one | 88773-23-3

• 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: (2R,6R)-2-chloro-4-benzoyloxy-6-methyl-2H-pyran-3-(6H)-one
• 英文别名: 3-O-benzoyl-α-D-actinospectosyl chloride；3-O-benzoyl-4,6-dideoxy-α-D-glycero-hex-3-enopyranosulosyl chloride；[(2R,6R)-6-chloro-2-methyl-5-oxo-2H-pyran-4-yl] benzoate
• CAS: 88773-23-3
• 化学式: C₁₃H₁₁ClO₄
• 分子量: 266.681
• InChiKey: RTGXWWCDOOGECS-PELKAZGASA-N

物化性质

• 沸点：
  412.1±45.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,6R)-2-chloro-4-benzoyloxy-6-methyl-2H-pyran-3-(6H)-one 在 4 A molecular sieve 、 silver alumosilicate reagent 、 potassium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 3.25h， 生成 bis-Cbz-spectinomycin
  参考文献：
  名称：

  A concise, stereocontrolled synthesis of spectinomycin

  摘要：

  A simple and concise synthesis of the antibiotic spectinomycin is described. The key step comprises a reaction cascade initiated by the P-selective 5-O-glycosylation of an N,N-blocked myo-1,3-inosadiamine 10 with a suitable actinospectosyl donor-the D-glucose-derived enol benzoate of 4,6-dideoxy-alpha-D-hex-3-enulosyl chloride 5 - which is spontaneously followed by regio- and stereospecific cyclohemiketalization and a 3-O -> 2-O-benzoyl group migration to directly elaborate the cis cisoid-trans-fused pyran-dioxane-cyclohexane framework of 1. The approach is flexible enough to be applied to other inosadiamines towards the generation of novel spectinomycin analogues. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.03.035
• 作为产物：
  描述：

  1,3-di-O-benzoyl-4,6-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose 在 盐酸 、 乙酰氯 作用下， 反应 12.0h， 以63%的产率得到(2R,6R)-2-chloro-4-benzoyloxy-6-methyl-2H-pyran-3-(6H)-one
  参考文献：
  名称：

  Lichtenthaler, Frieder W.; Loehe, Albert; Cuny, Eckehard, Liebigs Annalen der Chemie, 1983, # 11, p. 1973 - 1985

  摘要：

  DOI：

文献信息

• A Concise and General Method for Doubly Attaching 2-Ketosugars to Aglycon Diols: Synthesis of the Gomphosides and Spectinomycin
  作者：Frieder W. Lichtenthaler、Eckehard Cuny、Osamu Sakanaka

  DOI：10.1002/anie.200500434

  日期：2005.8.5
• Lichtenthaler, Frieder W.; Loehe, Albert; Cuny, Eckehard, Liebigs Annalen der Chemie, 1983, # 11, p. 1973 - 1985
  作者：Lichtenthaler, Frieder W.、Loehe, Albert、Cuny, Eckehard

  DOI：——

  日期：——
• A concise, stereocontrolled synthesis of spectinomycin
  作者：Eckehard Cuny、Frieder W. Lichtenthaler

  DOI：10.1016/j.tetasy.2006.03.035

  日期：2006.4

  A simple and concise synthesis of the antibiotic spectinomycin is described. The key step comprises a reaction cascade initiated by the P-selective 5-O-glycosylation of an N,N-blocked myo-1,3-inosadiamine 10 with a suitable actinospectosyl donor-the D-glucose-derived enol benzoate of 4,6-dideoxy-alpha-D-hex-3-enulosyl chloride 5 - which is spontaneously followed by regio- and stereospecific cyclohemiketalization and a 3-O -> 2-O-benzoyl group migration to directly elaborate the cis cisoid-trans-fused pyran-dioxane-cyclohexane framework of 1. The approach is flexible enough to be applied to other inosadiamines towards the generation of novel spectinomycin analogues. (c) 2006 Elsevier Ltd. All rights reserved.