(2S,4R)-2-(羟甲基)-4-(甲磺酰氧基)吡咯烷-1-羧酸叔丁酯 | 148017-07-6

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (2S,4R)-2-(羟甲基)-4-(甲磺酰氧基)吡咯烷-1-羧酸叔丁酯
• 英文名称: (2S,4R)-N-tetr-butoxycarbonyl-4-methanesulfonyloxy-2-hydroxymethylpyrrolidine
• 英文别名: 1-(N-Boc)-4(R)-O-mesyl-pyrrolidine-2(S)-methyl alcohol；(2S,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol；trans-N-t-BOC-O-mesyl-4-hydroxyl-L-prolinol；N-Boc-4R-O-mesyl-prolinol；(2S,4R)-Tert-butyl 2-(hydroxymethyl)-4-(methylsulfonyloxy)pyrrolidine-1-carboxylate；tert-butyl (2S,4R)-2-(hydroxymethyl)-4-methylsulfonyloxypyrrolidine-1-carboxylate
• CAS: 148017-07-6
• 化学式: C₁₁H₂₁NO₆S
• 分子量: 295.357
• InChiKey: GBUOWVDRNWNHOE-DTWKUNHWSA-N

物化性质

• 沸点：
  452.2±38.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,4R)-2-(羟甲基)-4-(甲磺酰氧基)吡咯烷-1-羧酸叔丁酯 在 三氯化铝 、 sodium methylate 、 苯甲醚 、 N,N-二异丙基乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.25h， 生成 多尼培南
  参考文献：
  名称：

  新型1β-甲基碳青霉烯抗生素S-4661的合成和修饰。

  摘要：

  我们描述了一种使用Mitsunobu反应将氨磺酰基氨基引入吡咯烷的C-2'位置的有效方法。用这种方法合成了S-4661，其N-甲基类似物和立体异构体，并研究了它们的结构活性关系。

  DOI：

  10.7164/antibiotics.49.478
• 作为产物：
  描述：

  N-Boc-反式-4-羟基-L-脯氨酸甲酯 在 吡啶 、 sodium tetrahydroborate 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 10.25h， 生成 (2S,4R)-2-(羟甲基)-4-(甲磺酰氧基)吡咯烷-1-羧酸叔丁酯
  参考文献：
  名称：

  C3′-endo-puckered pyrrolidine containing PNA has favorable geometry for RNA binding: Novel ethano locked PNA (ethano-PNA)

  摘要：

  A novel peptide nucleic acid (PNA) analogue is designed with a constraint in the aminoethyl segment of the aegPNA backbone so that the dihedral angle beta is restricted within 60-80 degrees, compatible to form PNA:RNA duplexes. The designed monomer is further functionalized with positively charged amino-/guanidino-groups. The appropriately protected monomers were synthesized and incorporated into aegPNA oligomers at predetermined positions and their binding abilities with cDNA and RNA were investigated. A single incorporation of the modified PNA monomer into a 12-mer PNA sequence resulted in stronger binding with complementary RNA over cDNA. No significant changes in the CD signatures of the derived duplexes of modified PNA with complementary RNA were observed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.015

文献信息

• Intermediates useful for the manufacture of carbapenem and a stereoselective manufacturing method therefor
  申请人：Eisai Co., Ltd.

  公开号：US06372914B1

  公开（公告）日：2002-04-16

  The present invention provides an efficient stereoselective method for manufacturing (2S,4S)-2-[[(R)-hydroxy-(3R)-cyclic amine-3-yl]methyl]pyrrolidine-4-thiol or a salt thereof which is useful as an intermediate for the manufacture of carbapenem and also provides the intermediate. A method for manufacturing which comprises the step of reacting a compound of the formula (I): (wherein, R1 is a lower alkylsulfonyl group, an optionally substituted arylsulfonyl group or an alkylsilyl group; and R2 is a protecting group for an amino group) with a compound of the formula (II): (wherein, R3 is a substituted or unsubstituted lower alkyl group or aryl group; X is an oxygen atom or a sulfur atom; Y is an azide group or a nitro group; and m is an integer of 2 to 5).

  本发明提供了一种高效的立体选择性方法，用于制造(2S,4S)-2-[[R)-羟基-(3R)-环胺-3-基]甲基]吡咯烷-4-硫醇或其盐，该化合物作为制造碳青霉烯的中间体具有重要用途，并提供了该中间体。 一种制造方法，包括以下步骤：使式(I)的化合物： （其中，R1为低级烷基磺酰基、可任选取代的芳基磺酰基或烷基硅基；R2为氨基保护基）与式(II)的化合物反应： （其中，R3为取代或未取代的低级烷基或芳基；X为氧原子或硫原子；Y为叠氮基或硝基；m为2至5的整数）。
• 4-Trifluoromethanesulfonamidyl prolinol tert-butyldiphenylsilyl ether as a highly efficient bifunctional organocatalyst for Michael addition of ketones and aldehydes to nitroolefins
  作者：Chao Wang、Chun Yu、Changlu Liu、Yungui Peng

  DOI：10.1016/j.tetlet.2009.02.211

  日期：2009.5

  4-Trifluoromethanesulfonamidyl prolinol tert-butyldiphenylsilyl ether bifunctional organocatalyst 3a is a highly efficient catalyst for the asymmetric Michael addition reactions of ketones and aldehydes to nitrostyrenes, leading to syn-selective adducts with excellent yields (>99%), high diastereoselectivities (up to 99:1 dr) and excellent enantioselectivities (up to 99% ee). Control experiments suggested that the

  4-三氟甲烷磺酰胺基脯氨醇叔丁基二苯基甲硅烷基醚双官能团有机催化剂3a是酮和醛不对称迈克尔加成反应成硝基苯乙烯的高效催化剂，可生成具有良好收率（> 99％），高非对映选择性（高达99％）的顺式选择性加合物：1 dr）和出色的对映选择性（高达99％ee）。对照实验表明，在吡咯烷环的4位大基团（–CH 2 OTBDPS）与磺酰胺基之间的反式关系对于实现高收率和立体选择性很重要。
• Pyrrolidylthiocarbapenem derivative
  申请人：Shionogi Seiyaku Kabushiki Kaisha

  公开号：US05317016A1

  公开（公告）日：1994-05-31

  A pyrrolidylthiocarbapenem derivative represented by Formula I is provided: ##STR1## wherein R.sup.1 is hydrogen or lower alkyl; R.sup.2, R.sup.3 and R.sup.4 are hydrogen, lower alkyl which can be substituted or an amino protecting group independently, or R.sup.2 and R.sup.3 together with a nitrogen atom to which R.sup.2 and R.sup.3 are bonded form a saturated or unsaturated cyclic group, or R.sup.2 and R.sup.4, or R.sup.3 and R.sup.4 together with two nitrogen atoms and one sulfur atom in the sufamide group form a saturated or unsaturated cyclic group; each cyclic group can further include at least one atom selected from the group consisting of oxygen, sulfur and nitrogen, and each cyclic group can be substituted; X.sup.1 is hydrogen or a hydroxy protecting group; X.sup.2 is hydrogen, a carboxy protecting group, an ammonio group, an alkali metal or an alkaline-earth metal; and Y.sup.2 is hydrogen or an amino protecting group.

  提供了一种由公式I表示的吡咯硫代碳青霉烯衍生物：##STR1## 其中R.sup.1是氢或低级烷基；R.sup.2、R.sup.3和R.sup.4是氢、可以独立地被取代的低级烷基或氨基保护基团，或者R.sup.2和R.sup.3与R.sup.2和R.sup.3键合的氮原子一起形成一个饱和或不饱和的环状基团，或者R.sup.2和R.sup.4，或者R.sup.3和R.sup.4与亚磺酰胺组中的两个氮原子和一个硫原子一起形成一个饱和或不饱和的环状基团；每个环状基团可以进一步包括至少一个由氧、硫和氮组成的原子，每个环状基团可以被取代；X.sup.1是氢或羟基保护基团；X.sup.2是氢、羧酸保护基团、铵离子、碱金属或碱土金属；Y.sup.2是氢或氨基保护基团。
• Synthesis of 4( S )-( N -Boc-amino)-2( S / R )-(thymin-1-ylmethyl)-pyrrolidine- N -1-acetic acid: a novel cyclic PNA with constrained flexibility
  作者：Moneesha D'Costa、Vaijayanti Kumar、Krishna N Ganesh

  DOI：10.1016/s0040-4039(01)02262-6

  日期：2002.1

  the pyrrolidyl ring could lead to pre-organization of the PNA structure and thus pose entropic advantages in binding to complementary nucleic acids. We report herein the synthesis of 4(S)-(N-Boc-amino)-2(S/R)-(thymin-1-ylmethyl)-pyrrolidine-N-1-acetic acids, their site-specific incorporation into PNA oligomers and their preliminary DNA binding properties.

  吡咯烷基PNA的出现是由于我们努力实现与互补核酸结合时氨基乙基缩水甘油基PNA结构的最佳微调。每个单元中的两个手性中心可产生四个非对映异构体，从而形成一个PNA单体和低聚物库。吡咯烷基环上的氮原子在生理pH下部分带电，导致产生阳离子PNA，这也导致水溶性增加。由吡咯烷基环引入的限制可能导致PNA结构的预组织，因此在与互补核酸结合方面具有熵的优势。我们在此报告4（S）-（N -Boc-氨基）-2（S / R）-（胸腺素-1-基甲基）-吡咯烷-N的合成-1-乙酸，它们在PNA低聚物中的位点特异性掺入及其初步的DNA结合特性。
• Stable NAD/NADH derivatives
  申请人：Roche Diabetes Care, Inc.

  公开号：US09399790B2

  公开（公告）日：2016-07-26

  The present invention provides for stable nicotinamide adenine dinucleotide (NAD/NADH) and nicotinamide adenine dinucleotide phosphate (NADP/NADPH) derivatives of formula (I), enzyme complexes of these derivatives and their use in biochemical detection methods and reagent kits.

  本发明提供了公式(I)稳定的烟酰胺腺嘌呤二核苷酸（NAD/NADH）和烟酰胺腺嘌呤二核苷酸磷酸（NADP/NADPH）衍生物，这些衍生物的酶复合物以及它们在生化检测方法和试剂盒中的使用。