Methanesulfonic acid (Z)-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-allyl ester | 663932-33-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: Methanesulfonic acid (Z)-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-allyl ester
• CAS: 663932-33-0
• 化学式: C₁₅H₂₄O₈S
• 分子量: 364.417
• InChiKey: VBGJINJCWYFPII-YXVJOSADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (Z)-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-allyl ester 在 吡啶 、 sodium hydroxide 、 甲苯-3,4-二硫酚 、 sodium hydride 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 、 xylene 为溶剂， 反应 7.0h， 生成 6-Acetamido-N-benzyl-6-deoxy-1,2:3,4-di-O-isopropylidene-β-L-glycero-D-galacto-heptodialdo-1,5-pyranose
  参考文献：
  名称：

  Stereocontrolled introduction of an amino group at C-6 of d-galactose via (3,3)-sigmatropic rearrangements—novel synthesis of lincosamine and 7-epi-lincosamine precursors

  摘要：

  A new and stereoselective route to the aminoglycoside components of the antibiotics lincomycin and clindamycin is presented, The key step involves diastereoselective introduction of the amino group at C-6 of D-galactose by (3,3)-sigmatropic rearrangements of the corresponding allylic (Z)-trifluoroacetimidate and (Z)- and (E)-allylic thiocyanates. Epoxidation of the resulting trifluoroacetamide with m-CPBA led to the epoxide with high threo-selectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02110-3
• 作为产物：
  描述：

  methyl (Z)-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-oct-6-enopyranuronate 在 二异丁基氢化铝 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 Methanesulfonic acid (Z)-3-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-allyl ester
  参考文献：
  名称：

  Stereocontrolled introduction of an amino group at C-6 of d-galactose via (3,3)-sigmatropic rearrangements—novel synthesis of lincosamine and 7-epi-lincosamine precursors

  摘要：

  A new and stereoselective route to the aminoglycoside components of the antibiotics lincomycin and clindamycin is presented, The key step involves diastereoselective introduction of the amino group at C-6 of D-galactose by (3,3)-sigmatropic rearrangements of the corresponding allylic (Z)-trifluoroacetimidate and (Z)- and (E)-allylic thiocyanates. Epoxidation of the resulting trifluoroacetamide with m-CPBA led to the epoxide with high threo-selectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)02110-3