1,4-dibromo-1,4-dideoxy-2,3-di-O-methyl-L-threitol | 70841-62-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-dibromo-1,4-dideoxy-2,3-di-O-methyl-L-threitol
• 英文别名: (R,R)-1,4-dibromo-2,3-dimethoxy-butane；1,4-dibromo-O²,O³-dimethyl-L-1,4-dideoxy-threitol；1,4-dibromo-1,4-dideoxy-2,3-di-O-methyl-l-threitol；(2R,3R)-1,4-dibromo-2,3-dimethoxybutane
• CAS: 70841-62-2
• 化学式: C₆H₁₂Br₂O₂
• 分子量: 275.968
• InChiKey: MNCSSBIISKCICX-WDSKDSINSA-N

物化性质

• 沸点：
  96-99 °C(Press: 5 Torr)
• 密度：
  1.648±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-dibromo-1,4-dideoxy-2,3-di-O-methyl-L-threitol 在 sodium iodide 三氯硅烷 、 碳酸氢钠 、 N,N-二甲基苯胺 作用下， 以 甲苯 、 均三甲苯 为溶剂， 生成 (3S,4S)-1-(2'-Diphenylphosphanyl-[1,1']binaphthalenyl-2-yl)-3,4-dimethoxy-pyrrolidine
  参考文献：
  名称：

  The synthesis of a new generation of MAP ligands containing two types of chiral elements for asymmetric catalysis

  摘要：

  A series of novel aminophosphine ligands containing both axial and central chirality have been synthesized for the first time from NOBIN and tartaric acid derivatives. Their capability for asymmetric induction in the Pd-catalyzed reaction of 1,3-diphenylprop-2-en-1-yl acetate and dimethyl malonate was investigated and the results clearly demonstrated that correct assembly of axial chirality in the scaffold and central chirality of the modification group was very important for achieving higher enantioselectivity in the reaction. In a matched case, the asymmetric allylation product could be obtained in 85.6% ec. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02056-1
• 作为产物：
  描述：

  (+)-(2S,3S)-1,4-Bis(tosyloxy)-2,3-dimethoxybutane 在 lithium bromide 作用下， 生成 1,4-dibromo-1,4-dideoxy-2,3-di-O-methyl-L-threitol
  参考文献：
  名称：

  Kowalik,J. et al., Polish Journal of Chemistry, 1979, vol. 53, p. 543 - 545

  摘要：

  DOI：

文献信息

• Synthesis of Phospholane 1-Oxide Having Oxygen Functional Groups from a 4-Bromobutylphoshinate Derivative
  作者：Tadashi Hanaya、Shigeru Kawase、Hiroshi Yamamoto

  DOI：10.3987/com-05-s(k)15

  日期：——

  Ethyl 4-bromo-2,3-dimethoxybutyl(phenyl)phosphinate (10a) was prepared from 2,3-di-0-methyl-L-threitol (12) in five steps. Reduction of 10a with sodium dihydrobis(2-methoxyethoxy)aluminate, followed by the action of hydrogen peroxide, afforded 3,4-dimethoxy-1-phenylphospholane I-oxide (3), while the reaction of 10a with magnesium in boiling THF resulted in the formation of ethyl 2-methoxy-3-butenyl(phenyl)phosphinate (26).
• Synthesis of Functionalized Phospholane Oxides and Phosphorinane Oxides from 1,4- and 1,5-Di-O-Mesyloxy Compounds
  作者：Tadashi Hanaya、Karsten Schürrle、Hiroshi Yamamoto

  DOI：10.3987/com-06-s(o)28

  日期：——

  Treatment of 1,4-di-0-mesyl-2,3-di-O-methyl-L-threitol (8b) with phenylphosphine in the presence of sodium hydride in DMSO, followed by the action of hydrogen peroxide, afforded 3,4-dimethoxy-1-phenylphospholane 1-oxide (7), while the same treatment of 1,5-di-O-mesyl-2,3,4-tri-O-methyl-mesoxylitol (11b) provided 2,3,4-trimethoxy-1-phenylphosphorinane 1-oxide (14).
• Kowalik,J. et al., Polish Journal of Chemistry, 1979, vol. 53, p. 543 - 545
  作者：Kowalik,J. et al.

  DOI：——

  日期：——
• The synthesis of a new generation of MAP ligands containing two types of chiral elements for asymmetric catalysis
  作者：Yi Wang、Xin Li、Kuiling Ding

  DOI：10.1016/s0040-4039(01)02056-1

  日期：2002.1

  A series of novel aminophosphine ligands containing both axial and central chirality have been synthesized for the first time from NOBIN and tartaric acid derivatives. Their capability for asymmetric induction in the Pd-catalyzed reaction of 1,3-diphenylprop-2-en-1-yl acetate and dimethyl malonate was investigated and the results clearly demonstrated that correct assembly of axial chirality in the scaffold and central chirality of the modification group was very important for achieving higher enantioselectivity in the reaction. In a matched case, the asymmetric allylation product could be obtained in 85.6% ec. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Hanaya, Tadashi; Akamatsu, Akihito; Kawase, Shigeru, Journal of Chemical Research - Part S, 1995, # 5, p. 194 - 195
  作者：Hanaya, Tadashi、Akamatsu, Akihito、Kawase, Shigeru、Yamamoto, Hiroshi

  DOI：——

  日期：——