(-)-(1'S,1''R,2''R,4R)-4-{1'-hydroxy-2'-[N-(2''-hydroxy-1''-methyl-2''-phenylethyl)-N-methylcarbamoyl]ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | 760188-32-7

• 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: (-)-(1'S,1''R,2''R,4R)-4-{1'-hydroxy-2'-[N-(2''-hydroxy-1''-methyl-2''-phenylethyl)-N-methylcarbamoyl]ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (4R)-4-[(1S)-1-hydroxy-3-[[(1R,2R)-1-hydroxy-1-phenylpropan-2-yl]-methylamino]-3-oxopropyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 760188-32-7
• 化学式: C₂₃H₃₆N₂O₆
• 分子量: 436.549
• InChiKey: PCOBVXPQIGVORW-LBKNJMOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  99.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-(1'S,1''R,2''R,4R)-4-{1'-hydroxy-2'-[N-(2''-hydroxy-1''-methyl-2''-phenylethyl)-N-methylcarbamoyl]ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 氢氧化钾 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 生成 ((4S,5R)-5-tert-Butoxycarbonylamino-2,2-dimethyl-[1,3]dioxan-4-yl)-acetic acid methyl ester
  参考文献：
  名称：

  Double Stereodifferentiation in the “Acetate-Type” Aldol Reaction with Garner's Aldehyde. Stereocontrolled Synthesis of Polyhydroxylated γ-Amino Carbonyl Compounds

  摘要：

  The aldol reaction of acetamide enolates with protected chiral alpha-amino-beta-hydroxy aldehyde 1 (Garner's aidehyde) has been performed in a stereocontrolled way under double stereodifferentiation conditions using pseudoephedrine as the additional chiral information source attached to the enolate reagent. In addition, the obtained adduct has been transformed into other valuable chiral building blocks such as gamma-amino-beta,delta-dihydroxy acids, esters, and ketones.

  DOI：

  10.1021/ol0487433
• 作为产物：
  描述：

  (R,R)-(-)-伪麻黄碱乙酰胺 、 (R)-(+)-3-Boc-2,2-二甲基恶唑啉-4-甲醛 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 以79%的产率得到(-)-(1'S,1''R,2''R,4R)-4-{1'-hydroxy-2'-[N-(2''-hydroxy-1''-methyl-2''-phenylethyl)-N-methylcarbamoyl]ethyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Double Stereodifferentiation in the “Acetate-Type” Aldol Reaction with Garner's Aldehyde. Stereocontrolled Synthesis of Polyhydroxylated γ-Amino Carbonyl Compounds

  摘要：

  The aldol reaction of acetamide enolates with protected chiral alpha-amino-beta-hydroxy aldehyde 1 (Garner's aidehyde) has been performed in a stereocontrolled way under double stereodifferentiation conditions using pseudoephedrine as the additional chiral information source attached to the enolate reagent. In addition, the obtained adduct has been transformed into other valuable chiral building blocks such as gamma-amino-beta,delta-dihydroxy acids, esters, and ketones.

  DOI：

  10.1021/ol0487433

文献信息

• Role of Pseudoephedrine as Chiral Auxiliary in the “Acetate-Type” Aldol Reaction with Chiral Aldehydes; Asymmetric Synthesis of Highly Functionalized Chiral Building Blocks
  作者：Marta Ocejo、Luisa Carrillo、Jose L. Vicario、Dolores Badía、Efraim Reyes

  DOI：10.1021/jo101878j

  日期：2011.1.21

  have studied in depth the aldol reaction between acetamide enolates and chiral α-heterosubstituted aldehydes using pseudoephedrine as chiral auxiliary under double stereodifferentiation conditions, showing that high diastereoselectivities can only be achieved under the matched combination of reagents and provided that the α-heteroatom-containing substituent of the chiral aldehyde is conveniently protected

  我们已经深入研究了在双立体分化条件下使用伪麻黄碱作为手性助剂的乙酰胺烯醇盐和手性α-杂取代醛之间的醛醇缩合反应，表明只有在匹配的试剂组合下才能实现高非对映选择性，并且前提是含α-杂原子手性醛的取代基被方便地保护。此外，所获得的高度官能化的羟醛已被用作非常有用的原料，用于立体控制制备其他令人感兴趣的化合物和手性结构单元，例如吡咯烷，吲哚并立兹，以及使用简单且高产率的致密官能化的β-羟基和β-氨基酮。方法论。
• Double Stereodifferentiation in the “Acetate-Type” Aldol Reaction with Garner's Aldehyde. Stereocontrolled Synthesis of Polyhydroxylated γ-Amino Carbonyl Compounds
  作者：Jose L. Vicario、Mónica Rodriguez、Dolores Badía、Luisa Carrillo、Efraim Reyes

  DOI：10.1021/ol0487433

  日期：2004.9.1

  The aldol reaction of acetamide enolates with protected chiral alpha-amino-beta-hydroxy aldehyde 1 (Garner's aidehyde) has been performed in a stereocontrolled way under double stereodifferentiation conditions using pseudoephedrine as the additional chiral information source attached to the enolate reagent. In addition, the obtained adduct has been transformed into other valuable chiral building blocks such as gamma-amino-beta,delta-dihydroxy acids, esters, and ketones.