(2S,2'R)-(1-benzyl-5-oxopyrrolidin-2-yl)-(tert-butyldimethylsilanyloxy)acetaldehyde | 445469-17-0

• 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: (2S,2'R)-(1-benzyl-5-oxopyrrolidin-2-yl)-(tert-butyldimethylsilanyloxy)acetaldehyde
• 英文别名: (2S)-2-[(2R)-1-benzyl-5-oxopyrrolidin-2-yl]-2-[tert-butyl(dimethyl)silyl]oxyacetaldehyde
• CAS: 445469-17-0
• 化学式: C₁₉H₂₉NO₃Si
• 分子量: 347.53
• InChiKey: UKKCACZJFCCEAR-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,2'R)-(1-benzyl-5-oxopyrrolidin-2-yl)-(tert-butyldimethylsilanyloxy)acetaldehyde 在 盐酸 、 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氨 、 水 、 乙腈 为溶剂， 反应 33.0h， 生成 (4a-carba-β-D-ribofuranuronosyl)amine
  参考文献：
  名称：

  Variable Strategy toward Carbasugars and Relatives. 4.¹ Viable Access to (4a-Carbapentofuranosyl)amines, (5a-Carbahexopyranosyl)amines, and Amino Acids Thereof

  摘要：

  A chiral, divergent synthesis of two carbafuranosylamines, I and 2, two carbapyranosylamines, 3 and 4, two carbafuranosylamino acids, 5 and 6, and two carbapyranosylamino acids, 7 and 8, has been achieved. Highlights of the procedure include the following: a diastereoselective crossed vinylogous Mukaiyama aldol coupling between N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole (TBSOP, 9) and 2,3-O-isopropylidene-D-glyceraldehyde (10) for the assembly of the target compound carbon backbone; a high-yielding silylative cycloaldolization that gives the cyclopentanoid and cyclohexanoid motifs; and a reductive or hydrolytic breakage of the lactam C(O)-N link to liberate the carbasugar and install the desired pseudo-anomeric amine and the hydroxymethyl or carboxyl functionalities. The sequences leading to trans-configured carbafuranosyl compounds 1 and 5 and carbapyranosyl compounds 3 and 7 were 12- and 13-step processes, with overall yields of 34%, 35%, 17%, and 16%. Cis-configured isomers 2, 4, 6, and 8 were obtained only in minor yields.

  DOI：

  10.1021/jo0257905
• 作为产物：
  描述：

  (1'S,2R,4''R)-2-[(2,2-dimethyl-[1,3]dioxolan-4-yl)hydroxymethyl]-5-oxo-2,5-dihydro-1H-pyrrole-1-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 2,6-二甲基吡啶 、 ammonium cerium(IV) nitrate 、 氢气 、 sodium acetate 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 33.67h， 生成 (2S,2'R)-(1-benzyl-5-oxopyrrolidin-2-yl)-(tert-butyldimethylsilanyloxy)acetaldehyde
  参考文献：
  名称：

  将氨基环戊烷羧酸接枝到RGD三肽序列上会产生低纳摩尔浓度的alphaVbeta3 / alphaVbeta5整联蛋白双结合剂。

  摘要：

  以手性非外消旋形式制备了11个γ-氨基环戊烷羧酸（Acpca）平台，包括四个二羟基代表分子（19-22），三个羟基类似物（34-36）和四个脱氧衍生物（30-33）。然后通过混合固相/溶液方案将这些简单的单元嫁接到Arg-Gly-Asp（RGD）三肽构架上，从而提供11种环-[-Arg-Gly-Asp-Acpca-]型大环类似物的集合体-11。评价各个化合物对αVbeta3和αVbeta5整联蛋白受体的结合亲和力。与参考化合物EMD121974和ST1646相比，类似物10表现出非常有趣的活性谱（IC50 / alphaVbeta3 = 1.5 nM； IC50 / alphaVbeta5 = 0.59 nM）。密切相关的同类物6、8 和9也被证明是出色的双重粘合剂，其活性水平在低纳摩尔范围内。确定了三维（3D）NMR溶液结构，并在选定的类似物上与参照化合物EMD121974进行了整合素α

  DOI：

  10.1021/jm050698x

文献信息

• Grafting Aminocyclopentane Carboxylic Acids onto the RGD Tripeptide Sequence Generates Low Nanomolar α_Vβ₃/α_Vβ₅ Integrin Dual Binders
  作者：Giovanni Casiraghi、Gloria Rassu、Luciana Auzzas、Paola Burreddu、Enrico Gaetani、Lucia Battistini、Franca Zanardi、Claudio Curti、Giuseppe Nicastro、Laura Belvisi、Ilaria Motto、Massimo Castorina、Giuseppe Giannini、Claudio Pisano

  DOI：10.1021/jm050698x

  日期：2005.12.1

  the low nanomolar range. The three-dimensional (3D) NMR solution structures were determined, and docking studies to X-ray crystal structure of the extracellular segment of integrin alphaVbeta3 in complex with the reference compound EMD121974 were performed on selected analogues to elucidate the interplay between structure and function in these systems and to evidence the subtle bases for receptorial recognition

  以手性非外消旋形式制备了11个γ-氨基环戊烷羧酸（Acpca）平台，包括四个二羟基代表分子（19-22），三个羟基类似物（34-36）和四个脱氧衍生物（30-33）。然后通过混合固相/溶液方案将这些简单的单元嫁接到Arg-Gly-Asp（RGD）三肽构架上，从而提供11种环-[-Arg-Gly-Asp-Acpca-]型大环类似物的集合体-11。评价各个化合物对αVbeta3和αVbeta5整联蛋白受体的结合亲和力。与参考化合物EMD121974和ST1646相比，类似物10表现出非常有趣的活性谱（IC50 / alphaVbeta3 = 1.5 nM； IC50 / alphaVbeta5 = 0.59 nM）。密切相关的同类物6、8 和9也被证明是出色的双重粘合剂，其活性水平在低纳摩尔范围内。确定了三维（3D）NMR溶液结构，并在选定的类似物上与参照化合物EMD121974进行了整合素α
• Variable Strategy toward Carbasugars and Relatives. 4.¹ Viable Access to (4a-Carbapentofuranosyl)amines, (5a-Carbahexopyranosyl)amines, and Amino Acids Thereof
  作者：Gloria Rassu、Luciana Auzzas、Luigi Pinna、Vincenzo Zambrano、Franca Zanardi、Lucia Battistini、Lucia Marzocchi、Domenico Acquotti、Giovanni Casiraghi

  DOI：10.1021/jo0257905

  日期：2002.7.1

  A chiral, divergent synthesis of two carbafuranosylamines, I and 2, two carbapyranosylamines, 3 and 4, two carbafuranosylamino acids, 5 and 6, and two carbapyranosylamino acids, 7 and 8, has been achieved. Highlights of the procedure include the following: a diastereoselective crossed vinylogous Mukaiyama aldol coupling between N-(tert-butoxycarbonyl)-2-[(tert-butyldimethylsilyl)oxy]pyrrole (TBSOP, 9) and 2,3-O-isopropylidene-D-glyceraldehyde (10) for the assembly of the target compound carbon backbone; a high-yielding silylative cycloaldolization that gives the cyclopentanoid and cyclohexanoid motifs; and a reductive or hydrolytic breakage of the lactam C(O)-N link to liberate the carbasugar and install the desired pseudo-anomeric amine and the hydroxymethyl or carboxyl functionalities. The sequences leading to trans-configured carbafuranosyl compounds 1 and 5 and carbapyranosyl compounds 3 and 7 were 12- and 13-step processes, with overall yields of 34%, 35%, 17%, and 16%. Cis-configured isomers 2, 4, 6, and 8 were obtained only in minor yields.