(1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester | 151074-57-6

• 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: (1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester
• 英文别名: methyl (1S,2R)-(-)-1-N-benzyloxycarbonylamino-2-hydroxymethylcyclopropanecarboxylate；methyl (1S,2R)-2-(hydroxymethyl)-1-(phenylmethoxycarbonylamino)cyclopropane-1-carboxylate
• CAS: 151074-57-6
• 化学式: C₁₄H₁₇NO₅
• 分子量: 279.293
• InChiKey: GVZUATDOHVLHHO-FZMZJTMJSA-N

物化性质

• 沸点：
  442.5±38.0 °C(predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester 在 盐酸 、 sodium tetrahydroborate 、 溶剂黄146 、 三乙胺 、 methyloxirane 作用下， 以 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 反应 10.34h， 生成 (1S,2R)-allonorcoronamic acid
  参考文献：
  名称：

  Enantioselective total syntheses of cyclopropane amino acids: Natural products and protein methanologs

  摘要：

  The syntheses of (-)-allo-coronamic acid, (-)-allo-norcoronamic acid, (-)-(Z)-2, 3-methanohomoserine, (-)-(Z)-2, 3-methanomethionine, and (2S, 3R)-Cbz-cyclo-Asp-OMe have been achieved in 45-68% overall yields from suitable intermediates derived from homochiral aminopentenoates which were obtained, in bun, from D-glyceraldehyde. The key synthetic step involves the quantitative and highly diastereoselective cyclopropanation of such precursors. The factors dealing with the control of stereoselectivity are highlighted and the main features in sidechain functionalization to the respective target molecules are discussed.

  DOI：

  10.1016/0957-4166(96)00038-9
• 作为产物：
  描述：

  (±)-Z-α-膦酰甘氨酸三甲酯 在 盐酸 、 甲醇 、 sodium tetrahydroborate 、 sodium periodate 、 二苯甲酮 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 124.96h， 生成 (1S,2R)-1-benzyloxycarbonylamino-2-hydroxymethyl-1-cyclopropanecarboxylic acid methyl ester
  参考文献：
  名称：

  Enantioselective total syntheses of cyclopropane amino acids: Natural products and protein methanologs

  摘要：

  The syntheses of (-)-allo-coronamic acid, (-)-allo-norcoronamic acid, (-)-(Z)-2, 3-methanohomoserine, (-)-(Z)-2, 3-methanomethionine, and (2S, 3R)-Cbz-cyclo-Asp-OMe have been achieved in 45-68% overall yields from suitable intermediates derived from homochiral aminopentenoates which were obtained, in bun, from D-glyceraldehyde. The key synthetic step involves the quantitative and highly diastereoselective cyclopropanation of such precursors. The factors dealing with the control of stereoselectivity are highlighted and the main features in sidechain functionalization to the respective target molecules are discussed.

  DOI：

  10.1016/0957-4166(96)00038-9

文献信息

• Enantioselective synthesis of cyclopropane aminoalcohols containing quaternary stereogenic centers
  作者：Joan Rifé、Rosa M. Ortuño

  DOI：10.1016/s0957-4166(99)00463-2

  日期：1999.10

  Some title compounds have been synthesized in enantiomerically pure form starting from d- or l-glyceraldehyde as chiral precursors. A new synthesis of (+)-(Z)-methanohomoserine, one of the key intermediates employed, is also described. The target molecules are densely functionalized. Thus, in addition to one or two hydroxyl groups on a side-chain, an amino group is attached to a quaternary carbon of

  从对-或1-甘油醛作为手性前体开始，已经以对映体纯的形式合成了一些标题化合物。还描述了一种新合成的（+）-（Z）-甲氨基高丝氨酸，它是所使用的关键中间体之一。靶分子被密集地官能化。因此，除了侧链上的一个或两个羟基之外，氨基还连接到环丙烷环的季碳上，并且该立体中心的第四取代基包含卤素原子，烷基或环氧基。具有醇，硫醚或酯的功能。这些化合物中的一些在合成新的环丙烷核苷中是有用的前体。
• Stereoselective Synthesis of Novel Types of Cyclopropyl Carbocyclic Nucleosides Containing Quaternary Stereogenic Centers
  作者：Elena Muray、Joan Rifé,、Vicenç Branchadell、Rosa M. Ortuño

  DOI：10.1021/jo025599v

  日期：2002.6.1

  of cyclopropyl carbocyclic nucleosides are described. The target products have been synthesized from suitable cyclopropane precursors obtained, in turn, from olefinic compounds derived from D-glyceraldehyde as a chiral precursor. Selective manipulation of the functional groups has allowed the preparation of enantiopure nucleosides, some of them displaying opposite chirality. All these molecules contain

  描述了新型的环丙基碳环核苷的多功能和立体控制合成词条。已经从合适的环丙烷前体合成了目标产物，所述合适的环丙烷前体又从作为手性前体的D-甘油醛衍生的烯烃化合物获得。官能团的选择性操作允许制备对映体纯的核苷，其中一些显示相反的手性。所有这些分子在环丙烷环的C-1或C-3处含有一个立体立体碳，并带有一个氨基，羟甲基或甲基作为附加取代基。在一种情况下，胸腺嘧啶直接与环丙烷连接。亚甲基单元用作其他合成核苷中的间隔基。
• First asymmetric @Synthesis of carnosadine
  作者：David J. Aitken、Dominique Guillaume、Henri-Philippe Husson

  DOI：10.1016/s0040-4020(01)80152-6

  日期：1993.1

  The first asymmetric synthesis of the naturally-occurring cyclopropane amino acid carnosadine, 1, has been carried out. Starting from the previously available chiral intermediate 2, appropriate amine protection and side-chain modifications permitted introduction of the key guanidyl substituent in a short and efficient synthesis to give the title compound in five steps and 45% overall yield.

  已经进行了天然存在的环丙烷氨基酸卡诺沙定1的第一次不对称合成。从先前可用的手性中间体2开始，适当的胺保护和侧链修饰允许在短而有效的合成中引入关键的胍基取代基，从而分五个步骤得到标题化合物，且总产率为45％。
• Synthesis of Novel Cyclopropyl Carbocyclic Nucleosides from (−)-(<i>Z</i>)-2,3-Methanohomoserine
  作者：Joan Rifé、Rosa M. Ortuño

  DOI：10.1021/ol990203w

  日期：1999.10.1

  [GRAPHICS]The new cyclopropyl carbocyclic nucleosides 1 and 2 have been synthesized by following short and efficient routes starting from conveniently protected (-)-(Z)-methanohomoserine derivative 3. Both products 1 and 2 bear a quaternary stereogenic center and have opposite chirality, Moreover, the adenine derivative 2 belongs to a new class of cyclopropyl nucleoside showing an amino alcohol function at C-1 in addition to a methylene spacer between the base and the carbocyclic ring.