1,4-Dideoxy-1,4-imino-2,3-di-O-isopropylidene-5-O-trityl-l-lyxitol | 149342-28-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1,4-Dideoxy-1,4-imino-2,3-di-O-isopropylidene-5-O-trityl-l-lyxitol
• 英文别名: (2S,3R,4S)-3,4-isopropylidenedioxy-2-trityloxymethylpyrrolidine；(2R,3S,4R)-3,4-isopropylidenedioxy-5-trityloxymethylpyrrolidine；1,4-dideoxy-2,3-di-O-isopropylidene-1,4-imino-5-O-trityl-L-lyxitol；(3aR,4S,6aS)-2,2-dimethyl-4-(trityloxymethyl)-4,5,6,6a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole
• CAS: 149342-28-9
• 化学式: C₂₇H₂₉NO₃
• 分子量: 415.532
• InChiKey: UZYQPQBDOKGINV-CCDWMCETSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  39.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-Dideoxy-1,4-imino-2,3-di-O-isopropylidene-5-O-trityl-l-lyxitol 在 盐酸 、 三氟乙酸 作用下， 反应 24.0h， 以90%的产率得到1,4-dideoxy-1,4-imino-L-lyxitol hydrochloride
  参考文献：
  名称：

  Hydroxylated pyrrolidines. Synthesis of 1,4-dideoxy-1,4-imino-L-lyxitol, 1,4,5-trideoxy-1,4-imino-D- and -L-lyxo-hexitol, 2,3,6-trideoxy-3,6-imino-D-glycero-L-altro- and -D-glycero-L-galacto-octitols, and of a chiral potential precursor of carbapenem systems

  摘要：

  Enantiospecific syntheses are reported for the title pyrrolidines, from carbohydrate precursors. An intermediate in one of the routes, ethyl 2,3,6-trideoxy-3,6-imino-4,5:7,8-di-O-isopropylidene-D-glycero-L-altro-octonate (23), could be converted in two steps into a beta-lactam.

  DOI：

  10.1016/s0040-4020(01)90234-0
• 作为产物：
  描述：

  N-Benzyl-1,4-dideoxy-1,4-imino-2,3-di-O-isopropylidene-5-O-trityl-L-lyxitol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 1,4-Dideoxy-1,4-imino-2,3-di-O-isopropylidene-5-O-trityl-l-lyxitol
  参考文献：
  名称：

  在C-5修饰的1,4-亚氨基-L-糖醇的合成及其作为GH38α-甘露糖苷酶抑制剂的评估。

  摘要：

  报道了在C-5位具有各种修饰的1，4-亚氨基-L-糖醇的合成方法。这些亚氨基-L-木糖醇核用于制备一系列N-（4-卤代苄基）聚羟基吡咯烷。评估了C-5修饰对黑腹果蝇，高尔基（GMIIb）和溶酶体（LManII）甘露糖苷酶和商业化的加拿大豆（Canavalia ensiformis）的杰克豆α-甘露糖苷酶对GH38α-甘露糖苷酶的抑制和选择性的影响。C-5处的修饰影响了它们对靶GMIIb酶的抑制活性。相反，未观察到吡咯烷对LManII的抑制作用。因此，亚氨基-L-糖醇核心的修饰是用于设计具有对靶GMIIb酶的期望选择性的抑制剂的合适基序。

  DOI：

  10.3762/bjoc.14.189

文献信息

• Chiral Pyrrolidine Derivatives as Catalysts for the Enantioselective Addition of Diethylzinc to Aldehydes.
  作者：Nobuo IKOTA、Hiroko INABA

  DOI：10.1248/cpb.44.587

  日期：——

  A chiral hydroxylated pyrrolidine derivative (4) and an N-(2-mercaptoethyl)pyrrolidine derivative (1c) were synthesized from D-ribonolactone and were used as chiral catalyst ligands in the reaction of diethylzinc and aldehydes. High asymmetric induction of up to 95% ee was observed in the addition to aromatic aldehydes using the chiral hydroxylated pyrrolidine derivative 4.

  合成了一个手性氢氧基吡咯烷衍生物（4）和一个N-(2-巯基乙基)吡咯烷衍生物（1c），这两个衍生物是从D-核糖内酯合成的，作为手性催化剂配体用于二乙基锌与醛的反应。在使用手性氢氧基吡咯烷衍生物4对芳香醛加成的反应中，观察到了高达95%的不对称诱导率（ee）。
• Synthesis of (2R, 3S,4R)-3,4-Dihydroxy-2-hydroxymethylpyrrolidine and (2S,3R,4S,5S)-3,4-Dihydroxy-2,5-dihydroxymethylpyrrolidine from (R)-Serine and D-Ribonolactone
  作者：Nobuo Ikota

  DOI：10.3987/com-93-6406

  日期：——

  (2R, 3S, 4R)-3,4-Dihydroxy-2-hydroxymethylpyrrolidine derivative (9, 10) and (2S, 3R, 4S, 5S)-3,4-dihydroxy-2,5-dihydroxymethylpyrrolidine derivatives (16, 17) were synthesized stereoselectively from (R)-serine and D-ribonolactone, respectively.

  (2R, 3S, 4R)-3,4-二羟基-2-羟甲基吡咯烷衍生物 (9, 10) 和 (2S, 3R, 4S, 5S)-3,4-二羟基-2,5-二羟甲基吡咯烷衍生物 (16, 17) 分别由 (R)-丝氨酸和 D-核糖醇酯通过具有选择性地合成。
• Stable chiral spirocyclic [5,5]-ammonium ylides using a metallo carbenoid approach
  作者：Daniele Muroni、Antonio Saba、Nicola Culeddu

  DOI：10.1016/j.tet.2005.11.020

  日期：2006.2

  Enantiomerically pure spiro[5,5]-ammonium ylides were obtained by Rh(II)-catalyzed decomposition of α-diazo-β-carbonylesters. In the crude decomposition mixtures, variable quantities of enamino-α,β-keto esters were detected as secondary products.

  通过Rh（II）催化的α-重氮-β-羰基酯的分解获得对映体纯的螺[5,5]-铵化铵。在粗分解混合物中，检测到不同数量的烯氨基-α，β-酮酯作为副产物。
• Synthesis of 1,4-imino-L-lyxitols modified at C-5 and their evaluation as inhibitors of GH38 α-mannosidases
  作者：Maroš Bella、Sergej Šesták、Ján Moncoľ、Miroslav Koóš、Monika Poláková

  DOI：10.3762/bjoc.14.189

  日期：——

  A synthetic approach to 1,4-imino-L-lyxitols with various modifications at the C-5 position is reported. These imino-L-lyxitol cores were used for the preparation of a series of N-(4-halobenzyl)polyhydroxypyrrolidines. An impact of the C-5 modification on the inhibition and selectivity against GH38 α-mannosidases from Drosophila melanogaster, the Golgi (GMIIb) and lysosomal (LManII) mannosidases and

  报道了在C-5位具有各种修饰的1，4-亚氨基-L-糖醇的合成方法。这些亚氨基-L-木糖醇核用于制备一系列N-（4-卤代苄基）聚羟基吡咯烷。评估了C-5修饰对黑腹果蝇，高尔基（GMIIb）和溶酶体（LManII）甘露糖苷酶和商业化的加拿大豆（Canavalia ensiformis）的杰克豆α-甘露糖苷酶对GH38α-甘露糖苷酶的抑制和选择性的影响。C-5处的修饰影响了它们对靶GMIIb酶的抑制活性。相反，未观察到吡咯烷对LManII的抑制作用。因此，亚氨基-L-糖醇核心的修饰是用于设计具有对靶GMIIb酶的期望选择性的抑制剂的合适基序。
• Hydroxylated pyrrolidines. Synthesis of 1,4-dideoxy-1,4-imino-L-lyxitol, 1,4,5-trideoxy-1,4-imino-D- and -L-lyxo-hexitol, 2,3,6-trideoxy-3,6-imino-D-glycero-L-altro- and -D-glycero-L-galacto-octitols, and of a chiral potential precursor of carbapenem systems
  作者：Deryk K. Thompson、Christine N. Hubert、Richard H. Wightman

  DOI：10.1016/s0040-4020(01)90234-0

  日期：1993.4

  Enantiospecific syntheses are reported for the title pyrrolidines, from carbohydrate precursors. An intermediate in one of the routes, ethyl 2,3,6-trideoxy-3,6-imino-4,5:7,8-di-O-isopropylidene-D-glycero-L-altro-octonate (23), could be converted in two steps into a beta-lactam.