methyl (2S)-2-[[(5-bromo-2-phenyl-1,3-oxazol-4-yl)methyl](phenylsulfonyl)amino]propanoate | 436843-87-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (2S)-2-[[(5-bromo-2-phenyl-1,3-oxazol-4-yl)methyl](phenylsulfonyl)amino]propanoate
• 英文别名: methyl (2S)-2-[benzenesulfonyl-[(5-bromo-2-phenyl-1,3-oxazol-4-yl)methyl]amino]propanoate
• CAS: 436843-87-7
• 化学式: C₂₀H₁₉BrN₂O₅S
• 分子量: 479.351
• InChiKey: SIKCOVRLFBVNSG-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  98.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-[[(5-bromo-2-phenyl-1,3-oxazol-4-yl)methyl](phenylsulfonyl)amino]propanoate 在 sodium tetrahydroborate 、 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (6S,7R)-7-(benzyloxy)-6-methyl-2-phenyl-5-(phenylsulfonyl)-4,5,6,7-tetrahydro[1,3]oxazolo[4,5-c]pyridine
  参考文献：
  名称：

  New Strategy for the Synthesis of Iminoglycitols from Amino Acids

  摘要：

  A novel strategy for the enantioselective synthesis of polyhydroxypiperidines, which can be considered as iminoglycitols or 2,6-dideoxyazasugars, was developed, alpha-Benzolsulfonylamino esters served as a C2N building block while 2-bromo-3-(bromomethyl)oxazoles and -thiazoles contributed a C3-unit to the final piperidine ring. At first a dihydropyridine ring was established via alkylation and bromine-lithium exchange. The keto group of the resulting 5,6-dihydro[1,3]oxazolo- and 5,6-dihydro[1,3]thiazolo[4,5-c]pyridin-7(4H)-ones was reduced and, after alkylation reactions, the azole ring was cleaved, thus providing heteroatom substituents for the target piperdines. Protected 5-amino-3,4-dihydroxy and 5-amino-3-hydroxy-4-thiohydroxypiperdines were obtained in the talose series while Mitsunobu reaction of the intermiediates provided access to the altrose series.

  DOI：

  10.1021/jo010665z
• 作为产物：
  描述：

  5-bromo-4-(bromomethyl)-2-phenyl-1,3-oxazole 、 N-benzenesulphonylalanine methyl ester 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以90%的产率得到methyl (2S)-2-[[(5-bromo-2-phenyl-1,3-oxazol-4-yl)methyl](phenylsulfonyl)amino]propanoate
  参考文献：
  名称：

  New Strategy for the Synthesis of Iminoglycitols from Amino Acids

  摘要：

  A novel strategy for the enantioselective synthesis of polyhydroxypiperidines, which can be considered as iminoglycitols or 2,6-dideoxyazasugars, was developed, alpha-Benzolsulfonylamino esters served as a C2N building block while 2-bromo-3-(bromomethyl)oxazoles and -thiazoles contributed a C3-unit to the final piperidine ring. At first a dihydropyridine ring was established via alkylation and bromine-lithium exchange. The keto group of the resulting 5,6-dihydro[1,3]oxazolo- and 5,6-dihydro[1,3]thiazolo[4,5-c]pyridin-7(4H)-ones was reduced and, after alkylation reactions, the azole ring was cleaved, thus providing heteroatom substituents for the target piperdines. Protected 5-amino-3,4-dihydroxy and 5-amino-3-hydroxy-4-thiohydroxypiperdines were obtained in the talose series while Mitsunobu reaction of the intermiediates provided access to the altrose series.

  DOI：

  10.1021/jo010665z

文献信息

• An all-cis 3,4-dihydroxy-5-aminopiperidine by a novel route to deoxydiamino sugars
  作者：Sauda Swaleh、Jürgen Liebscher

  DOI：10.1016/s0040-4039(99)00156-2

  日期：1999.3

  An (L)-diaza-1,6-dideoxytalose 7 as a first example of a new synthetic concept for aminodeoxy sugars by destruction of the 5-membered heterocyclic ring of condensed pyridones derived from natural amino acids and an o-bromo-bromomethyl 5-membered heterocycle is reported. (C) 1999 Elsevier Science Ltd. All rights reserved.
• New Strategy for the Synthesis of Iminoglycitols from Amino Acids
  作者：Sauda Swaleh、Jürgen Liebscher

  DOI：10.1021/jo010665z

  日期：2002.5.1

  A novel strategy for the enantioselective synthesis of polyhydroxypiperidines, which can be considered as iminoglycitols or 2,6-dideoxyazasugars, was developed, alpha-Benzolsulfonylamino esters served as a C2N building block while 2-bromo-3-(bromomethyl)oxazoles and -thiazoles contributed a C3-unit to the final piperidine ring. At first a dihydropyridine ring was established via alkylation and bromine-lithium exchange. The keto group of the resulting 5,6-dihydro[1,3]oxazolo- and 5,6-dihydro[1,3]thiazolo[4,5-c]pyridin-7(4H)-ones was reduced and, after alkylation reactions, the azole ring was cleaved, thus providing heteroatom substituents for the target piperdines. Protected 5-amino-3,4-dihydroxy and 5-amino-3-hydroxy-4-thiohydroxypiperdines were obtained in the talose series while Mitsunobu reaction of the intermiediates provided access to the altrose series.