dimethyl (2R,3R)-2,3-bis(prop-2-enoxy)butanedioate | 126863-01-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: dimethyl (2R,3R)-2,3-bis(prop-2-enoxy)butanedioate
• CAS: 126863-01-2
• 化学式: C₁₂H₁₈O₆
• 分子量: 258.271
• InChiKey: GPGIIPUFVNHXCD-NXEZZACHSA-N

物化性质

• 沸点：
  314.2±37.0 °C(Predicted)
• 密度：
  1.088±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl (2R,3R)-2,3-bis(prop-2-enoxy)butanedioate 、 [(3aR,4R,5R,7aS)-7-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-carbamic acid benzyl ester 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 、 9-borabicyclo[3.3.1]nonane dimer 作用下， 生成 (2R,3R)-2,3-Bis-{3-[(3aR,6R,7R,7aR)-6-benzyloxycarbonylamino-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxol-4-yl]-propoxy}-succinic acid dimethyl ester
  参考文献：
  名称：

  Scaffolded bis-azasugars: A dual warhead approach to glycosidase inhibition

  摘要：

  Double Suzuki coupling was achieved with vinyl bromide 7, synthesized from the bromobenzene microbial oxidation metabolite bromocyclohexadienediol 6 and alpha,omega-diborane coupling partners derived from the hydroboration of the corresponding diene. Ozonolysis and selective reduction protocols served to provide selectively the aia or pip tethered polyhydroxylated piperidine ring systems (bis-azabugars). The C-8 linked DMJ analogue 1 showed inhibitory activity against glycosidase enzymes. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10616-5
• 作为产物：
  描述：

  L-(+)-酒石酸二甲酯 、 3-溴丙烯 在 sodium hydride 、 18-冠醚-6 、 四丁基碘化铵 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以46%的产率得到dimethyl (2R,3R)-2,3-bis(prop-2-enoxy)butanedioate
  参考文献：
  名称：

  A quadruple ring-closing metathesis reaction in the synthesis of bis-spirocyclic compounds: extending the scope of metathesis chemistry

  摘要：

  The first example of a quadruple ring-closing metathesis reaction is reported. The reaction of the C2 symmetric octaene 3 afforded bis-spirocyclic compounds in high yield. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00161-8

文献信息

• Allyl ethyl carbonate/palladium (0), a new system for the one step conversion of alcohols into allyl ethers under neutral conditions
  作者：R. Lakhmiri、P. Lhoste、D. Sinou

  DOI：10.1016/s0040-4039(01)80770-x

  日期：1989.1

  Alcohols are converted in a one-step procedure into allyl ethers under neutral conditions, using allyl ethyl carbonate in the presence of a catalytic amount of palladium (0). Anomeric hydroxyls are selectively allylated in the presence of other hydroxyl groups.

  在催化量的钯（0）的存在下，使用碳酸烯丙基乙酯，在中性条件下，将醇一步一步转化为烯丙基醚。在其他羟基存在下，端基羟基被选择性烯丙基化。
• Scaffolded bis-azasugars: A dual warhead approach to glycosidase inhibition
  作者：Brian A. Johns、Carl R. Johnson

  DOI：10.1016/s0040-4039(97)10616-5

  日期：1998.2

  Double Suzuki coupling was achieved with vinyl bromide 7, synthesized from the bromobenzene microbial oxidation metabolite bromocyclohexadienediol 6 and alpha,omega-diborane coupling partners derived from the hydroboration of the corresponding diene. Ozonolysis and selective reduction protocols served to provide selectively the aia or pip tethered polyhydroxylated piperidine ring systems (bis-azabugars). The C-8 linked DMJ analogue 1 showed inhibitory activity against glycosidase enzymes. (C) 1998 Elsevier Science Ltd. All rights reserved.
• A quadruple ring-closing metathesis reaction in the synthesis of bis-spirocyclic compounds: extending the scope of metathesis chemistry
  作者：D WALLACE

  DOI：10.1016/s0040-4039(03)00161-8

  日期：2003.3.3

  The first example of a quadruple ring-closing metathesis reaction is reported. The reaction of the C2 symmetric octaene 3 afforded bis-spirocyclic compounds in high yield. (C) 2003 Elsevier Science Ltd. All rights reserved.