2-[2-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-3,6-dihydro-2H-pyran-3-yl]-N,N-dimethylacetamide | 500222-27-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2-[2-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-3,6-dihydro-2H-pyran-3-yl]-N,N-dimethylacetamide
• 英文别名: 2-[(2S,3R,6S)-6-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-phenylmethoxy-3,6-dihydro-2H-pyran-3-yl]-N,N-dimethylacetamide
• CAS: 500222-27-5
• 化学式: C₂₃H₃₇NO₄Si
• 分子量: 419.637
• InChiKey: JXFQKSQRDGVULQ-ONTIZHBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[2-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-3,6-dihydro-2H-pyran-3-yl]-N,N-dimethylacetamide 在 四丁基氟化铵 、 碘 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.5h， 生成 4-benzyloxy-6-hydroxymethyl-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
• 作为产物：
  描述：

  benzyl 2,3-dideoxy-α-D-glycero-hex-2-enopyranoside 在 咪唑 、 丙酸 作用下， 以 正己烷 、 二氯甲烷 、 xylene 为溶剂， 反应 15.0h， 生成 2-[2-benzyloxy-6-(tert-butyldimethylsilyloxymethyl)-3,6-dihydro-2H-pyran-3-yl]-N,N-dimethylacetamide
  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.