(S)-3-(benzyloxycarbonyl)-4-methyl-[1,2,3]oxathiazolidine 2,2-dioxide | 1007121-72-3

• 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: (S)-3-(benzyloxycarbonyl)-4-methyl-[1,2,3]oxathiazolidine 2,2-dioxide
• 英文别名: benzyl (5)-4-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide；(S)-3-Cbz-4-methyl-1,2,3-oxathiazolidine 2,2-dioxide；benzyl (4S)-4-methyl-2,2-dioxooxathiazolidine-3-carboxylate
• CAS: 1007121-72-3
• 化学式: C₁₁H₁₃NO₅S
• 分子量: 271.294
• InChiKey: CKCJEQFMSMZKEV-VIFPVBQESA-N

物化性质

• 沸点：
  386.5±35.0 °C(Predicted)
• 密度：
  1.386±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-3-(benzyloxycarbonyl)-4-methyl-[1,2,3]oxathiazolidine 2,2-dioxide 、 N-烯丙基对甲苯磺酰胺 在 氢氧化钾 、 盐酸 作用下， 以 乙腈 、 乙酸乙酯 为溶剂， 以95%的产率得到benzyl (S)-1-(N-allyl-4-methylbenzenesulfonamido)propan-2-ylcarbamate
  参考文献：
  名称：

  Synthesis of 2,6-Disubstituted Piperazines by a Diastereoselective Palladium-Catalyzed Hydroamination Reaction

  摘要：

  A highly diastereoselective intramolecular hydroamination is the key step in a modular synthesis of 2,6-disubstituted piperazines. The requisite hydroamination substrates were prepared in excellent yields by nucleophilic displacement of cyclic sulfamidates derived from amino acids. A variety of alkyl and aryl substituents at the 2-position were tolerated. The stereochemistry of the piperazines was determined to be trans by X-ray crystallography, which also showed the preferred conformation of the 2,6-disubstituted piperazine to be a twist-boat due to A(1,3) strain.

  DOI：

  10.1021/ol702891p
• 作为产物：
  描述：

  N-苄氧基羰基-L-丙氨醇 在 ruthenium trichloride 氯化亚砜 、 吡啶 、 sodium periodate 、 水 作用下， 以 乙腈 为溶剂， 反应 1.02h， 以63%的产率得到(S)-3-(benzyloxycarbonyl)-4-methyl-[1,2,3]oxathiazolidine 2,2-dioxide
  参考文献：
  名称：

  Synthesis of 2,6-Disubstituted Piperazines by a Diastereoselective Palladium-Catalyzed Hydroamination Reaction

  摘要：

  A highly diastereoselective intramolecular hydroamination is the key step in a modular synthesis of 2,6-disubstituted piperazines. The requisite hydroamination substrates were prepared in excellent yields by nucleophilic displacement of cyclic sulfamidates derived from amino acids. A variety of alkyl and aryl substituents at the 2-position were tolerated. The stereochemistry of the piperazines was determined to be trans by X-ray crystallography, which also showed the preferred conformation of the 2,6-disubstituted piperazine to be a twist-boat due to A(1,3) strain.

  DOI：

  10.1021/ol702891p

文献信息

• [EN] NOVEL METHODS FOR SYNTHETIZING ENANTIOPURE (S)-METHADONE, (R)-METHADONE, RACEMIC (R,S)-METHADONE AND RELATED ANALOGUE SUBSTANCES<br/>[FR] NOUVEAUX PROCÉDÉS DE SYNTHÈSE D'ÉNANTIOPURE (S)-MÉTHADONE, (R)-MÉTHADONE, (R,S)-MÉTHADONE RACÉMIQUE ET SUBSTANCES ANALOGUES ASSOCIÉES
  申请人：[en]UNIVERSITY OF PADOVA

  公开号：WO2022217013A1

  公开（公告）日：2022-10-13

  Methods for the synthesis of enantiopure (S)-methadone, (R)-methadone, (R,S)-methadone and related analogues starting from optically active or racemicN-substituted cyclic sulfamidates, orN-substituted aziridines with retention of stereochemical configuration. The methods avoid the formation of isomethadone-nitrile by-products observed under the previously reported conditions, namely the ring-opening reaction of the corresponding 1,1,2-trimethylaziridin-1-ium salt and the 2,2-diphenylacetonitrile anion, resulting in improved yields and facile purification operations.