(S)-N-α-benzyloxyacetyl-4-benzyl-5,5-dimethyloxazolidin-2-one | 496877-70-4

• 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: (S)-N-α-benzyloxyacetyl-4-benzyl-5,5-dimethyloxazolidin-2-one
• 英文别名: (S)-4-benzyl-2-(2'-benzyloxyacetyl)-5,5-dimethyloxazolidin-2-one；(4S)-4-benzyl-5,5-dimethyl-3-(2-phenylmethoxyacetyl)-1,3-oxazolidin-2-one
• CAS: 496877-70-4
• 化学式: C₂₁H₂₃NO₄
• 分子量: 353.418
• InChiKey: SRSSQLZSOUIFCA-SFHVURJKSA-N

物化性质

• 沸点：
  501.4±33.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  (S)-(-)-4-苄基-5,5-二甲基-2-恶唑烷酮	(S)-4-benzyl-5,5-dimethyloxazolidin-2-one	168297-85-6	C12H15NO2	205.257

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(2'S,3'R,4S)-4-benzyl-3-(2',4'-bis(benzyloxy)-3'-hydroxybutyryl)-5,5-dimethyloxazolidin-2-one	496877-71-5	C30H33NO6	503.595
  ——	(1''R,2'S,3'S,4S)-4-benzyl-3-(2'-benzyloxy-3'-(2'',2''-dimethyl-[1'',3'']dioxolan-4''-yl)-3'-hydroxy-propionyl)-5,5-dimethyl-oxazolidin-2-one	819799-55-8	C27H33NO7	483.562
  ——	(2'S,3'S,4S,4'S,5'R)-4-benzyl-3-(2',4'-bisbenzyloxy-3',5'-dihydroxy-5'-phenylpentanoyl)-5,5-dimethyl-oxazolidin-2-one	819799-49-0	C37H39NO7	609.719
  ——	(2'S,3'S,4S,4'R,5'R)-4-benzyl-3-[2',4'-bis(benzyloxy)-5'-(tert-butyldimethylsilanyloxy)-3'-hydroxyhexanoyl]-5,5-dimethyloxazolidin-2-one	846542-14-1	C38H51NO7Si	661.911
  ——	(2'S,3'R,4S,4'R,5'R)-4-benzyl-3-[2',4'-bis(benzyloxy)-5'-(tert-butyldimethylsilanyloxy)-3'-hydroxyhexanoyl]-5,5-dimethyloxazolidin-2-one	846542-13-0	C38H51NO7Si	661.911
  ——	(2'R,3'S,4R,4'R,5'R)-4-benzyl-3-[2',4'-bis(benzyloxy)-5'-(tert-butyldimethylsilanyloxy)-3'-hydroxyhexanoyl]-5,5-dimethyloxazolidin-2-one	846542-08-3	C38H51NO7Si	661.911
  ——	(2'S,3'R,4S,4'R,5'R)-4-benzyl-3-[2',4',6'-tris(benzyloxy)-5'-(tert-butyldimethylsilanyloxy)-3'-hydroxyhexanoyl]-5,5-dimethyloxazolidin-2-one	846542-11-8	C45H57NO8Si	768.035
  ——	(2'S,3'S,4S,4'R,5'R)-4-benzyl-3-[2',4',6'-tris(benzyloxy)-5'-(tert-butyldimethylsilanyloxy)-3'-hydroxyhexanoyl]-5,5-dimethyloxazolidin-2-one	846542-12-9	C45H57NO8Si	768.035
  ——	(2'R,3'S,4R,4'R,5'R)-4-benzyl-3-[2',4',6'-tris(benzyloxy)-5'-(tert-butyldimethylsilanyloxy)-3'-hydroxyhexanoyl]-5,5-dimethyloxazolidin-2-one	846542-07-2	C45H57NO8Si	768.035
  ——	(1''R,2'S,3'S,4S)-4-benzyl-3-[2'-benzyloxy-3'-(2'',2''-dimethyl-[1'',3'']dioxolan-4''-yl)-3'-(tert-butyl-dimethylsilanyloxy)-propionyl]-5,5-dimethyl-oxazolidin-2-one	819799-60-5	C33H47NO7Si	597.824

反应信息

• 作为反应物：
  描述：

  (S)-N-α-benzyloxyacetyl-4-benzyl-5,5-dimethyloxazolidin-2-one 在 咪唑 、 4-二甲氨基吡啶 、 三乙基硼 、 三氟甲磺酸 、 四丁基氟化铵 、 二异丁基氢化铝 、 potassium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.75h， 生成 2,4,6-tri-O-benzyl-α,β-D-galactopyranose
  参考文献：
  名称：

  The Asymmetric Synthesis ofd-Galactose via an Iterativesyn-Glycolate Aldol Strategy

  摘要：

  通过迭代的合成-乙醇醛酸策略，从简单的起始原料出发，经过八个步骤完成了 d-半乳糖的不对称合成，收率大于 14%。

  DOI：

  10.1055/s-2002-34215
• 作为产物：
  描述：

  苄氧基乙酰氯 、 (S)-(-)-4-苄基-5,5-二甲基-2-恶唑烷酮 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 以89%的产率得到(S)-N-α-benzyloxyacetyl-4-benzyl-5,5-dimethyloxazolidin-2-one
  参考文献：
  名称：

  N-α-Benzyloxyacetyl derivatives of (S)-4-benzyl-5,5-dimethyloxazolidin-2-one for the asymmetric synthesis of differentially protected α,β-dihydroxyaldehydes

  摘要：

  alpha-Dibenzylamino- and alpha-benzyloxy- derivatives of N-acetyl-(S)-4-benzyl-5,5-dimethyloxazolidin-2-one readily undergo highly stereoselective boron mediated syn-aldol reactions with a range of aromatic and aliphatic aldehydes, generating the syn-aldol products in good to excellent yields as single diastereoisomers after purification. In the alpha-dibenzylamino series, deprotection of the functionalised aldol fragments to the corresponding alpha-amino-beta-hydroxy methyl ester or alpha-amino-beta-hydroxyaldehyde proved problematic, with a range of N- and O-protecting groups giving mixtures of products arising from endocyclic and exocyclic cleavage pathways. However, in the et-benzyloxy series, O-silyl protection of the aldol products, and subsequent DIBAL reduction gives stereoselectively the corresponding N-1'-hydroxyalkyloxazolidin-2-ones, which undergo base promoted fragmentation to the desired highly functionalised and differentially protected alpha,beta-dihydroxyaldehydes in good yields and without loss of stereochemical integrity. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.123

文献信息

• Double diastereoselective SuperQuat glycolate aldol reactions: Application to the asymmetric synthesis of polyfunctionalised lactones
  作者：Stephen G. Davies、Rebecca L. Nicholson、Andrew D. Smith

  DOI：10.1039/b411724g

  日期：——

  Polyfunctionalised lactones with up to five contiguous stereocentres may be prepared with high stereocontrol by a double diastereoselective aldol protocol with protected homochiral α,β-dihydroxy- or α,β-γ-trihydroxyaldehydes and a chiral glycolate oxazolidinone, followed by subsequent O-desilylation and lactonisation.

  通过与受保护的同手性α,β-二羟基或α,β-γ-三羟基醛和手性羟基噁唑烷酮进行双非对映选择性醛醇反应，然后进行 O-去硅烷化和内酯化反应，可制备出具有最多五个连续立体中心的多官能团内酯，并具有很高的立体控制性。
• The Asymmetric Synthesis of<scp>d</scp>-Galactose via an Iterative<i>syn</i>-Glycolate Aldol Strategy
  作者：Stephen G. Davies、Rebecca L. Nicholson、Andrew D. Smith

  DOI：10.1055/s-2002-34215

  日期：——

  The asymmetric synthesis of d-galactose has been completed in eight steps and in >14% yield from simple starting materials via an iterative syn-glycolate aldol strategy.

  通过迭代的合成-乙醇醛酸策略，从简单的起始原料出发，经过八个步骤完成了 d-半乳糖的不对称合成，收率大于 14%。
• N-α-Benzyloxyacetyl derivatives of (S)-4-benzyl-5,5-dimethyloxazolidin-2-one for the asymmetric synthesis of differentially protected α,β-dihydroxyaldehydes
  作者：Stephen G. Davies、Ian A. Hunter、Rebecca L. Nicholson、Paul.M. Roberts、Edward D. Savory、Andrew D. Smith

  DOI：10.1016/j.tet.2004.05.123

  日期：2004.8

  alpha-Dibenzylamino- and alpha-benzyloxy- derivatives of N-acetyl-(S)-4-benzyl-5,5-dimethyloxazolidin-2-one readily undergo highly stereoselective boron mediated syn-aldol reactions with a range of aromatic and aliphatic aldehydes, generating the syn-aldol products in good to excellent yields as single diastereoisomers after purification. In the alpha-dibenzylamino series, deprotection of the functionalised aldol fragments to the corresponding alpha-amino-beta-hydroxy methyl ester or alpha-amino-beta-hydroxyaldehyde proved problematic, with a range of N- and O-protecting groups giving mixtures of products arising from endocyclic and exocyclic cleavage pathways. However, in the et-benzyloxy series, O-silyl protection of the aldol products, and subsequent DIBAL reduction gives stereoselectively the corresponding N-1'-hydroxyalkyloxazolidin-2-ones, which undergo base promoted fragmentation to the desired highly functionalised and differentially protected alpha,beta-dihydroxyaldehydes in good yields and without loss of stereochemical integrity. (C) 2004 Elsevier Ltd. All rights reserved.
• A SuperQuat glycolate aldol approach to the asymmetric synthesis of hexose monosaccharides
  作者：Stephen G. Davies、Rebecca L. Nicholson、Andrew D. Smith

  DOI：10.1039/b415943h

  日期：——

  A stereoselective two-carbon homologation protocol has been developed and applied to the asymmetric synthesis of the hexose monosaccharides D-galactose, D-fucose, D-idose, D-6-deoxyidose, D-talose and D-6-deoxytalose.

  我们开发了一种立体选择性双碳同源化方案，并将其应用于 D-半乳糖、D-岩藻糖、D-idose、D-6-脱氧idose、D-塔罗糖和 D-6-deoxytalose 六糖单糖的不对称合成。