4-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-7-iodo-3,3a,4,6,7,7a-hexahydrofuro[3,2-c]pyran-2-one | 500222-30-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: 4-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-7-iodo-3,3a,4,6,7,7a-hexahydrofuro[3,2-c]pyran-2-one
• 英文别名: (3aR,4S,6R,7R,7aS)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-iodo-4-phenylmethoxy-3,3a,4,6,7,7a-hexahydrofuro[3,2-c]pyran-2-one
• CAS: 500222-30-0
• 化学式: C₂₁H₃₁IO₅Si
• 分子量: 518.464
• InChiKey: KCARRYATQKVNQX-CJGGRQNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.69
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-7-iodo-3,3a,4,6,7,7a-hexahydrofuro[3,2-c]pyran-2-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以86%的产率得到2-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-3-(2-hydroxyethyl)-5-iodo-3,4,5,6-tetrahydro-2H-pyran-4-ol
  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：

  乙酰化葡萄烯糖 在 咪唑 、 碘 、 三氯化铁 、 丙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 xylene 为溶剂， 反应 29.25h， 生成 4-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-7-iodo-3,3a,4,6,7,7a-hexahydrofuro[3,2-c]pyran-2-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