methyl (4S,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-2,2-dimethyl-5-vinyl-1,3-dioxan-5-ylcarbamate | 1373934-60-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (4S,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-2,2-dimethyl-5-vinyl-1,3-dioxan-5-ylcarbamate
• CAS: 1373934-60-1
• 化学式: C₁₇H₃₃NO₅Si
• 分子量: 359.538
• InChiKey: WVRJQHRDHOPYRC-DYVFJYSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  66.02
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (4S,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-2,2-dimethyl-5-vinyl-1,3-dioxan-5-ylcarbamate 在 臭氧 、 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以80%的产率得到methyl (4S,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate
  参考文献：
  名称：

  An efficient synthesis of the polar part of sulfamisterin and its analogs

  摘要：

  An efficient synthesis of the polar part of sulfamisterin and its analogs starting from D-xylose is described. The corresponding allylic thiocyanates and trichloroacetimidates were subjected to aza-Claisen rearrangement that effectively generated a quaternary carbon having an amino group as one of the sub-stituents. Subsequent functional group interconversions afforded the highly functionalized branched aminopolyol 29 that is expected to have the crucial application in the construction of sulfamisterin. On the other hand, the second diastereoisomer 34 would be transformed to 2-epi-congener. With respect to the appropriate stereochemical arrangement, the prepared polar segments 29 and 34 can also be utilized for the synthesis of mycestericins (E, G) and their analogs. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.02.019
• 作为产物：
  描述：

  ethyl (4S,2E)-2-{4-[(tert-butyldimethylsilyloxy)methyl]-2,2-dimethyl-1,3-dioxan-5-ylidene}acetate 在 二异丁基氢化铝 、 三乙胺 、 2,4,6-三甲基苯甲腈N-氧化物 作用下， 以 甲醇 、 二氯甲烷 、 邻二甲苯 、 甲苯 、 乙腈 为溶剂， 反应 80.58h， 生成 methyl (4S,5S)-4-[(tert-butyldimethylsilyloxy)methyl]-2,2-dimethyl-5-vinyl-1,3-dioxan-5-ylcarbamate
  参考文献：
  名称：

  An efficient synthesis of the polar part of sulfamisterin and its analogs

  摘要：

  An efficient synthesis of the polar part of sulfamisterin and its analogs starting from D-xylose is described. The corresponding allylic thiocyanates and trichloroacetimidates were subjected to aza-Claisen rearrangement that effectively generated a quaternary carbon having an amino group as one of the sub-stituents. Subsequent functional group interconversions afforded the highly functionalized branched aminopolyol 29 that is expected to have the crucial application in the construction of sulfamisterin. On the other hand, the second diastereoisomer 34 would be transformed to 2-epi-congener. With respect to the appropriate stereochemical arrangement, the prepared polar segments 29 and 34 can also be utilized for the synthesis of mycestericins (E, G) and their analogs. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.02.019