(R)-2-benzyloxy-3-hydroxy-propionaldehyde | 76227-09-3

• 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: (R)-2-benzyloxy-3-hydroxy-propionaldehyde
• 英文别名: (R)-2-Benzyloxy-3-hydroxy-propionaldehyd；Propanal, 3-hydroxy-2-(phenylmethoxy)-, (2R)-；(2R)-3-hydroxy-2-phenylmethoxypropanal
• CAS: 76227-09-3
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: JDNBRBUDLGGLQH-JTQLQIEISA-N

物化性质

• 沸点：
  140 °C(Press: 0.005 Torr)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-benzyloxy-3-hydroxy-propionaldehyde 在 盐酸 、 硫酸 、 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 105.0h， 生成 (R)-3-(十六烷氧基)-2-(苯基甲氧基)-丙醛
  参考文献：
  名称：

  New optically pure dimethylacetals of glyceraldehydes and their application for lipid and phospholipid synthesis

  摘要：

  A convenient synthesis of new and enantiomerically pure 2-O-protected D-glyceraldehyde dimethylacetals as chiral C-3 building blocks for the synthesis of lipids and phospholipids is described. Benzyl- or allylethers are used as protecting groups in position 2 and 5 of D-mannitol. These intermediates are converted to 2-O-benzyl- or 2-O-allyl-D-glyceraldehyde dimethylacetals by cleavage with periodic acid in methanol. The two dimethylacetals are useful for the synthesis of mixed chain phospholipids with natural configuration of ester-ester, ester-ether or ether-ether composition. Also, triglycerides with three different alkyl chains, ester or ether, can be prepared. As an example of the versatility of the new intermediates, we describe the synthesis of 1-O-hexahecyl-2-O-acetyl-sn-glycero-3-phosphocholine, the so-called 'platelet activating factor' (PAF), via 1-O-hexadecyl-2-O-benzyl-sn-glycerol.

  DOI：

  10.1016/0009-3084(95)02445-o
• 作为产物：
  描述：

  2,5-di-O-benzyl-D-mannitol 在 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (R)-2-benzyloxy-3-hydroxy-propionaldehyde
  参考文献：
  名称：

  New optically pure dimethylacetals of glyceraldehydes and their application for lipid and phospholipid synthesis

  摘要：

  A convenient synthesis of new and enantiomerically pure 2-O-protected D-glyceraldehyde dimethylacetals as chiral C-3 building blocks for the synthesis of lipids and phospholipids is described. Benzyl- or allylethers are used as protecting groups in position 2 and 5 of D-mannitol. These intermediates are converted to 2-O-benzyl- or 2-O-allyl-D-glyceraldehyde dimethylacetals by cleavage with periodic acid in methanol. The two dimethylacetals are useful for the synthesis of mixed chain phospholipids with natural configuration of ester-ester, ester-ether or ether-ether composition. Also, triglycerides with three different alkyl chains, ester or ether, can be prepared. As an example of the versatility of the new intermediates, we describe the synthesis of 1-O-hexahecyl-2-O-acetyl-sn-glycero-3-phosphocholine, the so-called 'platelet activating factor' (PAF), via 1-O-hexadecyl-2-O-benzyl-sn-glycerol.

  DOI：

  10.1016/0009-3084(95)02445-o

文献信息

• Synthesis of enantiomerically pure pyrrolidines by stereospecific cycloaddition of azomethine ylides with enones
  作者：M. Pätzel、G. Galley、P.G. Jones、A. Chrapkowsky

  DOI：10.1016/s0040-4039(00)73839-1

  日期：1993.9

  alkoxy or amino substituent in γ-position react with azomethine ylides 3 (obtained from glycine imines) in the presence of DBU/AgOAc giving enantiomerically pure pyrrolidine derivatives 4 in a stereospecific manner.

  在DBU / AgOAc的存在下，几种在γ位带有手性烷氧基或氨基取代基的（E）-α，β-不饱和酮（烯酮）2与偶氮甲亚胺3（由甘氨酸亚胺获得）反应，得到对映体纯的吡咯烷衍生物4以立体定向的方式。
• Pyranoside derivatives of 3-deoxyald-2-ulosonic acids
  作者：Daniel Charon、Ladislas Szabó

  DOI：10.1039/p19800001971

  日期：——

  increases the stability of the glycosidic bond of 3deoxy-D-manno-octulosonic acid while the benzyl substituent in position 5 exerts only a weak stabilising effect. 2-O-Benzyl-D-glyceraldehyde, when treated with oxaloacetic acid in the presence of Ni2+ at pH 7 in the absence of borate, yields 5-O-benzyl-3-deoxyhex-2-ulosonic acids, the predominant D-erythro-isomer being isolated as its methyl ester.

  在pH值为11.5的0.2 M四硼酸钠溶液中以及在Ni 2+的存在下，2- O-苄基-D-阿拉伯糖与草酰乙酸反应，生成50-60％的5- O-苄基-3-脱氧辛酯-2- ulosonic羧酸（混合的d -葡糖-和d -甘露-异构体）。这些甲酯分离，并且将的α甲基糖苷d -甘露制备异构体。化合物的构象通过在250 MHz处的核磁共振光谱确定。观察到羧基的酯化极大地提高了3deoxy- D的糖苷键的稳定性-甘露糖基-辛磺酸，而第5位的苄基取代基仅发挥弱的稳定作用。2- ø苯甲基d甘油醛，与草酰乙酸在Ni的存在时处理2+在pH 7在不存在硼酸盐时，得到5- ø -苄基-3- deoxyhex -2- ulosonic酸，主要的d -分离作为其甲基酯的赤型异构体。
• Synthesis of iminopolyols via Henry reaction: a short route to the α-manno- sidase inhibitor 1,4-dideoxy-1,4-imino-D-mannitol and to amino analogues†,1
  作者：Frank-Michael Kieß、Philip Poggendorf、Volker Jäger、Frank-Michael Kieß、Sylviane Picasso

  DOI：10.1039/a706915d

  日期：——

  The α-mannosidase inhibitor 1,4-dideoxy-1,4-imino-D-mannitol (DIM) as well as amino analogues of DIM and of deoxy-manno-nojirimycin, respectively, have been prepared using a diastereoselective nitroaldol addition as the key step.

  α-甘露糖苷酶抑制剂1,4-脱氧-1,4-亚氨基-D-甘露醇（DIM）以及DIM和脱氧甘露诺里米霉素的氨基类似物已利用一种对映选择性硝基醛醇反应作为关键步骤进行合成。
• Diastereofacial selectivity of the cycloaddition of diazo compounds to enones
  作者：G Galley、M Pätzel、P.G Jones

  DOI：10.1016/0040-4020(94)01049-6

  日期：1995.2

  Chiral α,β-unsaturated γ-alkoxy- or γ-amino-ketones (enones) 1 react with diazo compounds in a stereoselective manner affording conjugated Δ2-pyrazolines 5 and 6. In all cases syn-selectivity for the cycloaddition was observed. The diastereomeric ratio is improved at lower temperatures, but no significant influence of high pressure is observed. Carrying out this reaction with (E) and (Z) derivatives

  手性α，β不饱和γ -烷氧基或γ氨基酮（烯酮）1用在以立体选择性方式重氮化合物，得到偶联反应Δ 2 -pyrazolines 5和6。在所有情况下SYN -选择性环加成进行了观察。在较低的温度下，非对映异构体比例有所提高，但是没有观察到高压的显着影响。用相同的烯酮1的（E）和（Z）衍生物进行该反应，得到相同的产物。
• Wehner, Volkmar; Jaeger, Volker, Angewandte Chemie, 1990, vol. 102, # 10, p. 1180 - 1182
  作者：Wehner, Volkmar、Jaeger, Volker

  DOI：——

  日期：——