(3,4,6-tri-O-acetyl-2-deoxy-α-D-erythro-hex-2-enopyranosyl)benzene | 78465-52-8

• 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: (3,4,6-tri-O-acetyl-2-deoxy-α-D-erythro-hex-2-enopyranosyl)benzene
• 英文别名: 3,4,6-tri-O-acetyl-2-desoxy-α-D-erythro-hex-2-enopyranosylbenzene；(2R,3R,6S)-2-(acetoxymethyl)-6-phenyl-3,6-dihydro-2H-pyran-3,4-diyl diacetate；[(2R,3R,6S)-3,4-diacetyloxy-6-phenyl-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 78465-52-8
• 化学式: C₁₈H₂₀O₇
• 分子量: 348.353
• InChiKey: MSXPOIWCKNKFMG-JQHSSLGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  88.13
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3,4,6-tri-O-acetyl-2-deoxy-α-D-erythro-hex-2-enopyranosyl)benzene 在 盐酸羟胺 作用下， 以 吡啶 为溶剂， 以75%的产率得到Acetic acid (2R,3S,6S)-2-acetoxymethyl-4-[(E)-hydroxyimino]-6-phenyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Nouvelle voie d'acces aux c-glycosides。

  摘要：

  DOI：

  10.1016/0040-4039(81)80119-0
• 作为产物：
  描述：

  苯 、 Tri-O-acetyl-D-glucal 在 palladium diacetate 溶剂黄146 作用下， 以41%的产率得到(3,4,6-tri-O-acetyl-2-deoxy-α-D-erythro-hex-2-enopyranosyl)benzene
  参考文献：
  名称：

  Nouvelle voie d'acces aux c-glycosides。

  摘要：

  DOI：

  10.1016/0040-4039(81)80119-0

文献信息

• Synthesis of (2-deoxy-α-d-glyc-2-enopyranosyl)arenes by stereospecific counjugate-addition of organocopper reagents to peracetylated hex-1-enopyran-3-uloses
  作者：Véronique Bellosta、Stanislas Czernecki

  DOI：10.1016/s0008-6215(00)90892-9

  日期：1987.12

  Abstract The reaction of peracetylated 1,5-anhydro-2-deoxyhex-1-eno-3-uloses with higher-order cyanoorganocuprate in oxolane at low temperature in the presence of acetic anhydride afforded the corresponding glycosylarenes in good yields. A complete stereocontrol could be achieved, leading to the α- d anomer without epimerization at C-4.The configuration of the new products was established by spectroscopic

  摘要在乙酸酐的存在下，乙氧基存在下，过乙酰化的1,5-脱水-2-脱氧己基-1-壬基-3 ulose与高阶氰基有机戊酸酯在环氧乙烷中的低温反应可得到相应的糖基芳烃，收率很高。可以实现完全的立体控制，导致α-d异构体在C-4处不发生差向异构化。通过光谱方法确定新产物的构型，并将其转变为结晶母体肟，并根据立体电子学来讨论其构象。效果。
• TEMPO-Promoted Domino Heck–Suzuki Arylation: Diastereoselective <i>Cis</i>-Diarylation of Glycals and Pseudoglycals
  作者：Anil Kumar Kusunuru、Chaitanya K. Jaladanki、Madhu Babu Tatina、Prasad V. Bharatam、Debaraj Mukherjee

  DOI：10.1021/acs.orglett.5b01722

  日期：2015.8.7

  A palladium-catalyzed regio- and diastereoselective diarylation of glycals and pseudoglycals, which is a kind of Heck-Suzuki arylation, is described. A wide range of arylboronic acids reacted under these conditions smoothly. Selectivity was C1-C2(alpha,alpha) in the case of glycals but C2-C3(beta,beta) for pseudoglycals. Quantum chemical analysis has been carried out to establish the reaction mechanism, which may involve Pd(II)/Pd(O). TEMPO plays a key role in the formation of diaryl glycoside due to its radical nature.
• Czernecki, Stanislas; Dechavanne, Veronique, Canadian Journal of Chemistry, 1983, vol. 61, p. 533 - 540
  作者：Czernecki, Stanislas、Dechavanne, Veronique

  DOI：——

  日期：——
• BELLOSTA, V.;CZERNECKI, S.;PERLAT, M. -C., J. CARBOHYDR. CHEM., 7,(1988) N 1, 141-149
  作者：BELLOSTA, V.、CZERNECKI, S.、PERLAT, M. -C.

  DOI：——

  日期：——