(3S,4R)-3-Methyl-4-((2R,4S,5R)-2-methyl-4-trityloxymethyl-[1,3]dioxan-5-yloxy)-azetidin-2-one | 355129-44-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (3S,4R)-3-Methyl-4-((2R,4S,5R)-2-methyl-4-trityloxymethyl-[1,3]dioxan-5-yloxy)-azetidin-2-one
• CAS: 355129-44-1
• 化学式: C₂₉H₃₁NO₅
• 分子量: 473.569
• InChiKey: IUWDSJHSKYYKBW-JTYTYNNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  35.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 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：

  (3S,4R)-3-Methyl-4-((2R,4S,5R)-2-methyl-4-trityloxymethyl-[1,3]dioxan-5-yloxy)-azetidin-2-one 在 氨 、 sodium 作用下， 以74%的产率得到(3S,4R)-4-((2R,4S,5R)-4-Hydroxymethyl-2-methyl-[1,3]dioxan-5-yloxy)-3-methyl-azetidin-2-one
  参考文献：
  名称：

  Stereocontrolled formation of cephams from 1,3-O-ethylidene-l-erythritol

  摘要：

  [2+2]Cycloaddition of chlorosulfonyl isocyanate to (Z)-1,3-O-ethylidene-2-0-propenyl-4-0-trityl-L-erythritol proceeds with excellent stereoselectivity to afford the corresponding (R)-4'-alkoxy-azetidin-2-one which can be transformed into 5-oxa-cepham by intramolecular alkylation of the p-lactam nitrogen atom. Cepham having the alternative (S) configuration at the bridgehead carbon atom can be achieved by another methodology based on alkylation of the nitrogen atom in 4-vinyloxy-aze-tidin-2-one by the suitably protected 1,3-ethylidene-L-erythritol followed by intramolecular displacement of the vinyloxy group. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00167-7
• 作为产物：
  描述：

  (2R,3S)-3-Methyl-2-((2R,4S,5R)-2-methyl-4-trityloxymethyl-[1,3]dioxan-5-yloxy)-4-oxo-azetidine-1-sulfonyl chloride 在 红铝 作用下， 生成 (3S,4R)-3-Methyl-4-((2R,4S,5R)-2-methyl-4-trityloxymethyl-[1,3]dioxan-5-yloxy)-azetidin-2-one
  参考文献：
  名称：

  Stereocontrolled formation of cephams from 1,3-O-ethylidene-l-erythritol

  摘要：

  [2+2]Cycloaddition of chlorosulfonyl isocyanate to (Z)-1,3-O-ethylidene-2-0-propenyl-4-0-trityl-L-erythritol proceeds with excellent stereoselectivity to afford the corresponding (R)-4'-alkoxy-azetidin-2-one which can be transformed into 5-oxa-cepham by intramolecular alkylation of the p-lactam nitrogen atom. Cepham having the alternative (S) configuration at the bridgehead carbon atom can be achieved by another methodology based on alkylation of the nitrogen atom in 4-vinyloxy-aze-tidin-2-one by the suitably protected 1,3-ethylidene-L-erythritol followed by intramolecular displacement of the vinyloxy group. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00167-7