D-arabinitol pentaacetate | 5346-78-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: D-arabinitol pentaacetate
• 英文别名: 1,2,3,4,5-Penta-O-acetyl-D-arabinitol；2R,4R-3S-pentitol pentaacetate；(+)-D-arabitol pentaacetate；penta-O-acetyl-D-arabinitol；D-arabinitol penta-acetate；penta-O-acetyl-D-arabitol；Arabinitol pentaacetate；[(2R,4R)-2,3,4,5-tetraacetyloxypentyl] acetate
• CAS: 5346-78-1；5401-55-8；6330-69-4；7208-42-6；26674-23-7；74033-71-9；85761-13-3
• 化学式: C₁₅H₂₂O₁₀
• 分子量: 362.334
• InChiKey: NVKPIAUSOPISJK-ZIAGYGMSSA-N

物化性质

• 沸点：
  396.5±35.0 °C(Predicted)
• 密度：
  1.229±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2,3,4,5,6-alpha-D-葡萄糖五乙酸酯 以 苯 为溶剂， 生成 D-arabinitol pentaacetate
  参考文献：
  名称：

  Photolysis of penta-O-acetyl-aldehydo-D-glucose

  摘要：

  DOI：

  10.1021/jo00816a054

文献信息

• Reaction of sugar allyltins with aldehydes. A remarkable difference in reactivity between furanose and pyranose organometallic derivatives
  作者：Sławomir Jarosz、Stanisław Skóra、Katarzyna Szewczyk、Zbigniew Ciunik

  DOI：10.1016/s0957-4166(01)00331-7

  日期：2001.7

  The reaction of organometallic derivatives of monosaccharides with aldehydes catalyzed with BF3·OEt2 was studied. A significant difference in reactivity between the pyranosidic and furanosidic allyltins was noted. The former reacted readily with aldehydes affording precursors of higher carbon sugars with very high stereoselectivity, while the latter underwent rearrangement with elimination of the stannyl

  研究了单糖的有机金属衍生物与BF 3 ·OEt 2催化的醛类的反应。注意到吡喃硅烷基和呋喃基硅烷基烯丙基锡之间的反应性有显着差异。前者容易与醛反应，从而提供具有非常高的立体选择性的高级碳糖的前体，而后者在与醛反应之前进行了重排，消除了苯乙烯基部分。
• Prebiotic carbohydrate synthesis: zinc–proline catalyzes direct aqueous aldol reactions of α-hydroxy aldehydes and ketones
  作者：Jacob Kofoed、Jean-Louis Reymond、Tamis Darbre

  DOI：10.1039/b501512j

  日期：——

  Zn–proline catalyzed aldolisation of glycoladehyde gave mainly tetroses whereas in the cross-aldolisation of glycoladehyde and rac-glyceraldehyde, pentoses accounted for 60% of the sugars formed with 20% of ribose.

  邻–脯氨酸催化的乙二醛醛醇反应主要生成四碳糖，而在乙二醛与外消旋甘油醛的交叉醛醇反应中，形成的糖类中有60%为五碳糖，其中20%为核糖。
• Asymmetric dihydroxylation of chiral olefins. High control of diastereofacial selection
  作者：Tohru Oishi、Kyo-ichiro Iida、Masahiro Hirama

  DOI：10.1016/s0040-4039(00)73639-2

  日期：1993.5

  Highly diastereoselective dihydroxylation of 4,5-dihydroxy-2-pentenoate with osmium tetroxide using chiral N,N'-dialkyl-2,2′-bipyrrolidine ligands (1) is described. Either syn or anti selection was achieved for acetate (2d) and methyl ether (2e) by employing the enantiomeric ligands.

  描述了使用手性N，N′-二烷基-2，2′-联吡咯烷配体（1）用四氧化对4，5-二羟基-2-戊烯酸酯的高度非对映选择性二羟基化。通过使用对映异构体配体，可以对乙酸盐（2d）和甲基醚（2e）进行顺式或反式选择。
• Acetolysis of a 2,4-O-benzylidene-l-ribo-hex-5-enitol derivative
  作者：János Kuszmann、Benjámin Podányi

  DOI：10.1016/0008-6215(94)80036-7

  日期：1994.5

  Abstract Acetolysis of ( Z )-1,3-di- O -acetyl-2,4- O -benzylidene-5,6-dideoxy-6- C -(2,4-dichlorophenyl)- l - ribo -hex-5-enitol afforded, besides 2- C -[( S )-acetoxy(2,4-dichlorophenyl)methyl]-3,4,6-tri- O -acetyl-2-deoxy-β- d - allo - and - gluco -hexopyranosylbenzene, ( E )-1,2,3,4-tetra- O -acetyl-5,6-dideoxy-6- C -(2,4-dichlorophenyl)- d - lyxo - and - l - ribo -hex-5-enitol as main products. The

  摘要（Z）-1,3-二-O-乙酰基-2,4-O-亚苄基-5,6-二脱氧-6-C-（2,4-二氯苯基）-1-核糖-hex-5的乙解-2-烯醇，除了2-C-[（S）-乙酰氧基（2,4-二氯苯基）甲基] -3,4,6-三-O-乙酰基-2-脱氧-β-d-异位-和-葡萄糖-己基吡喃糖基苯，（E）-1,2,3,4-四-O-乙酰基-5,6-二脱氧-6- C-（2,4-二氯苯基）-d-lyxo-和-l-ribo -hex -5-烯醇为主要产品。该反应的速率以及产物的比例取决于C-3的手性。通过乙酰解相应的1-赤-戊-4-烯醇衍生物来证实这一点。
• Stereoselective synthesis of β,γ-unsaturated- and β,γ-epoxy glycerol derivatives starting with glyceraldehyde and their use in the synthesis of alditols
  作者：Masato Kusakabe、Fumie Sato

  DOI：10.1039/c39860000989

  日期：——

  Highly stereoselective addition of vinylcopper and vinylcuprate compounds to glyceraldehyde acetonide affords both syn- and anti-β,γ-unsaturated glycerol derivatives, respectively, which can readily be converted into all the possible steric isomers of the β,γ-epoxy glycerol derivatives, which are useful intermediates in the synthesis of alditols.

  将乙烯基铜和乙烯基铜酸盐化合物高度立体选择性地添加到甘油醛丙酮化物中，分别得到顺式和反式β，γ-不饱和甘油衍生物，它们可以容易地转化为β，γ-环氧甘油衍生物的所有可能的空间异构体，在醛糖醇的合成中是有用的中间体。