((2R,3S,4S)-2-Hydroxymethyl-3-methoxy-3,4-dihydro-2H-pyran-4-yl)-methyl-carbamic acid tert-butyl ester | 174148-57-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((2R,3S,4S)-2-Hydroxymethyl-3-methoxy-3,4-dihydro-2H-pyran-4-yl)-methyl-carbamic acid tert-butyl ester
• CAS: 174148-57-3
• 化学式: C₁₃H₂₃NO₅
• 分子量: 273.329
• InChiKey: IRLHHWFAERSJJW-AXFHLTTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.14
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  68.23
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ((2R,3S,4S)-2-Hydroxymethyl-3-methoxy-3,4-dihydro-2H-pyran-4-yl)-methyl-carbamic acid tert-butyl ester 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 二甲基二环氧乙烷 、 sodium hydride 作用下， 生成 Acetic acid (1R,5R,7R,8S,9S)-8-methoxy-7-(4-methoxy-benzyloxymethyl)-2-methyl-3-oxo-4,6-dioxa-2-aza-bicyclo[3.3.1]non-9-yl ester
  参考文献：
  名称：

  Staurosporine and ent-Staurosporine:  The First Total Syntheses, Prospects for a Regioselective Approach, and Activity Profiles¹

  摘要：

  The total syntheses of staurosporine and ent-staurosporine have been achieved. Both glycosidic bonds were built from glycal precursors. The first was constructed by intermolecular coupling of an indole anion with a 1,2-anhydrosugar derived from an endo-glycal by direct epoxidation. The second bond was assembled from an exo-glycal by intramolecular iodoglycosylation.

  DOI：

  10.1021/ja952907g
• 作为产物：
  描述：

  ((2R,3S,4S)-3-Methoxy-2-triisopropylsilanyloxymethyl-3,4-dihydro-2H-pyran-4-yl)-methyl-carbamic acid tert-butyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到((2R,3S,4S)-2-Hydroxymethyl-3-methoxy-3,4-dihydro-2H-pyran-4-yl)-methyl-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Staurosporine and ent-Staurosporine:  The First Total Syntheses, Prospects for a Regioselective Approach, and Activity Profiles¹

  摘要：

  The total syntheses of staurosporine and ent-staurosporine have been achieved. Both glycosidic bonds were built from glycal precursors. The first was constructed by intermolecular coupling of an indole anion with a 1,2-anhydrosugar derived from an endo-glycal by direct epoxidation. The second bond was assembled from an exo-glycal by intramolecular iodoglycosylation.

  DOI：

  10.1021/ja952907g