4-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-3a,7a-dihydro-3H,4H-furo[3,2-c]pyran-2-one | 500222-32-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 4-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-3a,7a-dihydro-3H,4H-furo[3,2-c]pyran-2-one
• 英文别名: (3aR,4S,7aR)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-phenylmethoxy-3,3a,4,7a-tetrahydrofuro[3,2-c]pyran-2-one
• CAS: 500222-32-2
• 化学式: C₂₁H₃₀O₅Si
• 分子量: 390.552
• InChiKey: XUMFOWZHENKHKH-GGPKGHCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 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)-3a,7a-dihydro-3H,4H-furo[3,2-c]pyran-2-one 在 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以93%的产率得到[2-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-4-hydroxy-3,4-dihydro-2H-pyran-3-yl]acetic acid
  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]-N,N-dimethylacetamide 在 碘 、 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 、 水 为溶剂， 反应 22.0h， 生成 4-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-3a,7a-dihydro-3H,4H-furo[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

文献信息

• HIGHLY DEOXYGENATED SUGARS. I. C2-BRANCHED GLUCOSE DERIVATIVES AND CARBON LINKED DEOXYGENATED DISACCHARIDES^*
  作者：Karsten Krohn、Ulrich Flörke、Dietmar Gehle

  DOI：10.1081/car-120014904

  日期：2002.1.10

  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.