[2-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-3,6-dihydro-2H-pyran-3-yl]acetaldehyde | 500222-34-4

• 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: [2-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-3,6-dihydro-2H-pyran-3-yl]acetaldehyde
• CAS: 500222-34-4
• 化学式: C₂₁H₃₂O₄Si
• 分子量: 376.568
• InChiKey: FKKXBTDTDZXNRY-UFYCRDLUSA-N

物化性质

• 沸点：
  436.8±45.0 °C(predicted)
• 密度：
  1.03±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 、 [2-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-3,6-dihydro-2H-pyran-3-yl]acetaldehyde 在 zinc(II) chloride 、 盐酸 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 以77%的产率得到2-[2-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-3,6-dihydro-2H-pyran-3-ylmethyl]-2,3-dihydropyran-4-one
  参考文献：
  名称：

  HIGHLY DEOXYGENATED SUGARS. I. C2-BRANCHED GLUCOSE DERIVATIVES AND CARBON LINKED DEOXYGENATED DISACCHARIDES^*

  摘要：

  Triacetylglucal (1) is converted with high alpha-selectivity (>9:1) to the corresponding 2,3-unsaturated allyl and benzyl glycosides 2 and 3 using ferric chloride as the catalyst. The 6-O-silyl-protected allylic alcohol 5 is transformed to the 3,4-unsaturated C2-branched ester 6 or the amide 7 by Claisen rearrangement. The highly deoxygenated iodo lactone 8, resulting from the amide 6 by iodolactonization, is a versatile starting material for chiral building blocks 9-12. The 3,4-unsaturated C2-branched ester 6 is reduced to the aldehyde 14 and converted to a carbon linked disaccharide analogue 16 via cycloaddition with Danishefky's diene.

  DOI：

  10.1081/car-120014904
• 作为产物：
  描述：

  2-[2-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-3,6-dihydro-2H-pyran-3-yl]ethanol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以92%的产率得到[2-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-3,6-dihydro-2H-pyran-3-yl]acetaldehyde
  参考文献：
  名称：

  HIGHLY DEOXYGENATED SUGARS. I. C2-BRANCHED GLUCOSE DERIVATIVES AND CARBON LINKED DEOXYGENATED DISACCHARIDES^*

  摘要：

  Triacetylglucal (1) is converted with high alpha-selectivity (>9:1) to the corresponding 2,3-unsaturated allyl and benzyl glycosides 2 and 3 using ferric chloride as the catalyst. The 6-O-silyl-protected allylic alcohol 5 is transformed to the 3,4-unsaturated C2-branched ester 6 or the amide 7 by Claisen rearrangement. The highly deoxygenated iodo lactone 8, resulting from the amide 6 by iodolactonization, is a versatile starting material for chiral building blocks 9-12. The 3,4-unsaturated C2-branched ester 6 is reduced to the aldehyde 14 and converted to a carbon linked disaccharide analogue 16 via cycloaddition with Danishefky's diene.

  DOI：

  10.1081/car-120014904