methyl (4aS,6R,7R,8S,8aR)-4-(benzenesulfonyl)-3-methyl-7,8-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-6,7,8,8a-tetrahydro-4aH-pyrano[3,2-b][1,4]thiazine-2-carboxylate | 226255-24-9

• 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: methyl (4aS,6R,7R,8S,8aR)-4-(benzenesulfonyl)-3-methyl-7,8-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-6,7,8,8a-tetrahydro-4aH-pyrano[3,2-b][1,4]thiazine-2-carboxylate
• CAS: 226255-24-9
• 化学式: C₃₈H₃₉NO₈S₂
• 分子量: 701.862
• InChiKey: VIJZZVIIMZAFPP-NKJDNRDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  49
• 可旋转键数：
  14
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  134
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl (4aS,6R,7R,8S,8aR)-4-(benzenesulfonyl)-3-methyl-7,8-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-6,7,8,8a-tetrahydro-4aH-pyrano[3,2-b][1,4]thiazine-2-carboxylate 在 臭氧 作用下， 以81%的产率得到methyl 2-[(2S,3R,4S,5R,6R)-2-[acetyl(benzenesulfonyl)amino]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]sulfanyl-2-oxoacetate
  参考文献：
  名称：

  Glycosyl Transfer to Nitrogen via Cycloaddition

  摘要：

  [GRAPHICS]This letter describes the reduction to practice of a novel concept for functionalization of the anomeric carbon of carbohydrates with a nitrogen substituent. Thus, bisheterodienes with a thiono sulfur terminus and a sulfonylimine terminus are shown to undergo cycloaddition smoothly and stereoselectively to three different glycals.

  DOI：

  10.1021/ol990583l
• 作为产物：
  描述：

  乙酰乙酸甲酯 在 2,6-二甲基吡啶 、 对甲苯磺酸 作用下， 以 氯仿 、 苯 为溶剂， 反应 0.83h， 生成 methyl (4aS,6R,7R,8S,8aR)-4-(benzenesulfonyl)-3-methyl-7,8-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-6,7,8,8a-tetrahydro-4aH-pyrano[3,2-b][1,4]thiazine-2-carboxylate
  参考文献：
  名称：

  Glycosyl Transfer to Nitrogen via Cycloaddition

  摘要：

  [GRAPHICS]This letter describes the reduction to practice of a novel concept for functionalization of the anomeric carbon of carbohydrates with a nitrogen substituent. Thus, bisheterodienes with a thiono sulfur terminus and a sulfonylimine terminus are shown to undergo cycloaddition smoothly and stereoselectively to three different glycals.

  DOI：

  10.1021/ol990583l

文献信息

• Glycosyl Transfer to Nitrogen via Cycloaddition
  作者：Baoqing Li、Richard W. Franck、Giuseppe Capozzi、Stefano Menichetti、Cristina Nativi

  DOI：10.1021/ol990583l

  日期：1999.7.1

  [GRAPHICS]This letter describes the reduction to practice of a novel concept for functionalization of the anomeric carbon of carbohydrates with a nitrogen substituent. Thus, bisheterodienes with a thiono sulfur terminus and a sulfonylimine terminus are shown to undergo cycloaddition smoothly and stereoselectively to three different glycals.