(1R)-N-benzyl-1-[(2R,3S)-3-[[tert-butyl(diphenyl)silyl]oxymethyl]oxiran-2-yl]prop-2-en-1-amine | 357278-33-2

• 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: (1R)-N-benzyl-1-[(2R,3S)-3-[[tert-butyl(diphenyl)silyl]oxymethyl]oxiran-2-yl]prop-2-en-1-amine
• CAS: 357278-33-2
• 化学式: C₂₉H₃₅NO₂Si
• 分子量: 457.688
• InChiKey: WLNWUGBQMBRBOK-OZNIXHKMSA-N

物化性质

• 沸点：
  525.4±38.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.67
• 重原子数：
  33
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  33.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R)-N-benzyl-1-[(2R,3S)-3-[[tert-butyl(diphenyl)silyl]oxymethyl]oxiran-2-yl]prop-2-en-1-amine 在 四丁基氟化铵 、 silica gel 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 40.0h， 生成 (4R,5S)-3-Benzyl-5-((S)-1,2-dihydroxy-ethyl)-4-vinyl-oxazolidin-2-one
  参考文献：
  名称：

  Stereoselective Access to the Versatile 4-Aminohex-5-ene-1,2,3-triol Pattern

  摘要：

  We developed a stereocontrolled route allowing potential access to the eight isomers of 4-benzylaminohex-5-ene-1,2,3-triol in two or four steps and ca. 50% yield from readily available chiral nonracemic cis- or trans-alpha,beta-epoxyimine precursors. A new (NH4)(2)CO3-based carboxylation/intramolecular cyclization sequence allowed regio- and stereocontrolled C-3 epoxide opening while neat C-2 hydrolysis was ensured by simple aqueous acidic treatment.

  DOI：

  10.1021/jo048766v
• 作为产物：
  描述：

  ((2RS,3SR)-3-(tert-butyldiphenylsilanyloxymethyl)oxiranyl)methanol 在 4 A molecular sieve 、 三氟化硼乙醚 、 2-碘酰基苯甲酸 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 生成 (1R)-N-benzyl-1-[(2R,3S)-3-[[tert-butyl(diphenyl)silyl]oxymethyl]oxiran-2-yl]prop-2-en-1-amine
  参考文献：
  名称：

  Asymmetric syntheses of (–)-lentiginosine and an original pyrrolizidinic analogue thereof from a versatile epoxyamine intermediate

  摘要：

  本文介绍了如何通过简单的五步顺序，从手性乙烯基环氧胺中获得天然 (â)-lentiginosine 及其吡咯烷类似物。在氨基三醇 5 和 6 上谨慎使用 RCM 反应是该合成途径的关键特征。对目标化合物的δ-淀粉葡萄糖苷酶抑制活性进行了评估，结果表明更容易获得的吡咯烷类似物具有与(â)-龙胆苷类似的抑制活性。

  DOI：

  10.1039/b505303j

文献信息

• Concise asymmetric syntheses of (–)-lentiginosine and of its pyrrolizidinic analogue
  作者：Tahar Ayad、Yves Génisson、Michel Baltas、Liliane Gorrichon

  DOI：10.1039/b212217k

  日期：2003.2.20

  (−)-Lentiginosine and its pyrrolizidinic analogue have been prepared in a straightforward five-step sequence from a versatile chiral cis-α,β-epoxyamine.

  (â)-Lentiginosine 及其吡咯烷类似物是由一种多功能手性顺式-δ,δ²-环氧胺通过简单的五个步骤制备而成的。
• A Flexible Route Towards Five-Membered Ring Imino Sugars and Their Novel 2-Deoxy-2-fluoro Analogues
  作者：Tahar Ayad、Yves Génisson、Sylvain Broussy、Michel Baltas、Liliane Gorrichon

  DOI：10.1002/ejoc.200300163

  日期：2003.8

  A flexible route towards five-membered ring imino sugars starting from a chiral α,β-epoxy aldehyde has been developed. The approach relies on the use of the versatile epoxyamine intermediate 4, from which regiocontrolled epoxide opening affords diastereoselective access to trisubstituted pyrrolidines. Described here is the nucleophilic attack at C-2 of the pivotal epoxypyrrolidine 10, leading to the

  已经开发了一种从手性 α,β-环氧醛开始制备五元环亚氨基糖的灵活途径。该方法依赖于多功能环氧胺中间体 4 的使用，从中区域控制的环氧化物开环可以非对映选择性地获得三取代的吡咯烷。这里描述的是在关键环氧吡咯烷 10 的 C-2 上的亲核攻击，导致生物相关的亚氨基糖 1,4-dideoxy-1,4-imino-D-arabinitol (2) 和 1,4-dideoxy-1， 4-亚氨基-L-半乳糖醇 (3) 及其新型 2-脱氧-2-氟类似物，经过乙烯基部分的氧化处理。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• A New Access to Polyhydroxylated Pyrrolidines from Epoxyaldehydes
  作者：Tahar Ayad、Yves Génisson、Michel Baltas、Liliane Gorrichon

  DOI：10.1055/s-2001-14593

  日期：——

  Our approach relies on the stereocontrolled vinylation of a chiral α,β-epoxyimine derived from the corresponding aldehyde. Regioselective opening of the oxirane with carbonate anion allowed the formation of an oxazolidinone intermediate from which the glucosidase inhibitor 1,4-dideoxy-1,4-imino-d-glucitol (14) was synthesised. Direct cyclisation into a 2-vinyl-3,4-epoxypyrrolidine afforded a valuable intermediate for the preparation of synthetic azasugar analogues.

  我们的方法依赖于从相应的醛中衍生出的手性δ±,δ²-环氧亚胺的立体控制乙烯基化。用碳酸阴离子对环氧乙烷进行区域选择性开环，可形成恶唑烷酮中间体，并由此合成出葡萄糖苷酶抑制剂 1,4-二脱氧-1,4-亚氨基-d-葡萄糖醇 (14)。直接环化成 2-乙烯基-3,4-环氧吡咯烷后，就得到了制备合成氮杂糖类似物的重要中间体。
• New approach to carbamoyl-polyoxamic acid derivatives through an oxazolidinone synthon
  作者：Magalie Collet、Yves Génisson、Michel Baltas

  DOI：10.1016/j.tetasy.2007.06.002

  日期：2007.6

  A key oxazolidinone synthon was obtained through condensation of vinyl magnesium with an epoxyimine, followed by a carbonation/cyclisation reaction in the presence of ammonium carbonate. Oxidative ozonolysis after protection and carbamolylation (optional) afforded the (5-0-carbamoyl-)polyoxamic derivatives in 9% (or 14%) total yield in six (or four) steps. (c) 2007 Elsevier Ltd. All rights reserved.
• Asymmetric syntheses of (–)-lentiginosine and an original pyrrolizidinic analogue thereof from a versatile epoxyamine intermediate
  作者：Tahar Ayad、Yves Génisson、Michel Baltas

  DOI：10.1039/b505303j

  日期：——

  Ready access to natural (−)-lentiginosine and its pyrrolizidinic analogue from a chiral vinylic epoxyamine in a straightforward five-step sequence is presented. Careful use of the RCM reaction on aminotriols 5 and 6 constitutes the key feature of the synthetic pathway. The α-amyloglucosidase inhibitory activities of the target compounds were evaluated and showed that the more easily accessible pyrrolizidinic analogue possesses an inhibitory activity quite similar to that of (−)-lentiginosine.

  本文介绍了如何通过简单的五步顺序，从手性乙烯基环氧胺中获得天然 (â)-lentiginosine 及其吡咯烷类似物。在氨基三醇 5 和 6 上谨慎使用 RCM 反应是该合成途径的关键特征。对目标化合物的δ-淀粉葡萄糖苷酶抑制活性进行了评估，结果表明更容易获得的吡咯烷类似物具有与(â)-龙胆苷类似的抑制活性。