di-O-benzoyl-L-arabinal | 25874-19-5

• 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: di-O-benzoyl-L-arabinal
• 英文别名: di-O-benzoyl-D-xylal；3,4-di-O-benzoyl-D-xylal；3,4-Di-O-benzoyl-1,2-dideoxy-D-threo-pent-1-enopyranose；[(3R,4R)-4-benzoyloxy-3,4-dihydro-2H-pyran-3-yl] benzoate
• CAS: 25874-19-5
• 化学式: C₁₉H₁₆O₅
• 分子量: 324.333
• InChiKey: PCOGNAVGXHCLFZ-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  di-O-benzoyl-L-arabinal 生成 methyl 5-[(2R)-oxiran-2-yl]pentanoate
  参考文献：
  名称：

  CABATEEBA, K. E.;XAXALINA, N. V.;TOLSTIKOV, A. G., 26 KONF. MOL. UCHENYX I SPETS. IN-TA ORGAN. XIMII AN YCCP, KIEV, MAJ, 19+

  摘要：

  DOI：
• 作为产物：
  描述：

  D-xylal 生成 di-O-benzoyl-L-arabinal
  参考文献：
  名称：

  TOLSTIKOV, A. G.;XAXALINA, N. V.;SAVATEEVA, E. E.;SPIRIXIN, L. V.;ODINOKO+, ZH. ORGAN. XIMII, 25,(1989) N, S. 787-792

  摘要：

  DOI：

文献信息

• Thio-click reaction of 2-deoxy-<i>exo</i>-glycals towards new glycomimetics: stereoselective synthesis of <i>C</i>-2-deoxy-<scp>d</scp>-glycopyranosyl compounds
  作者：János József、László Juhász、László Somsák

  DOI：10.1039/c8nj06138f

  日期：——

  conditions. Photoinitiated thiol–ene additions of these exo-glycals resulted in the corresponding C-(2-deoxy-D-glycopyranosyl)methyl sulfides in medium to good yields with exclusive regio- and stereoselectivities in most cases. Several disaccharide mimics with a C–S moiety in place of the glycosidic oxygen were also obtained.

  一系列的2-脱氧吡喃葡萄糖基氰化物与d -阿拉伯糖，d -来苏，d -赤，和d -苏式构型，由相应的烯糖合成通过2-脱氧吡喃葡萄糖基乙酸盐。通过在甲苯磺酰肼存在下用NaH 2 PO 2 / Ra-Ni还原将氰化物转化为脱水醛糖甲苯磺酰hydr。在改良的Bamford–Stevens条件下，甲苯磺酰azo提供了2-deoxy- exo - glycals。这些外糖的光引发硫醇烯加成反应产生了相应的在大多数情况下，C-（2-脱氧-D-甘露糖基糖基）甲基硫化物具有中等至良好的收率，并且具有独特的区域选择性和立体选择性。还获得了几个具有C–S部分代替糖苷氧的二糖模拟物。
• Stereoselective Thallium-induced Ring Contraction of Glycals
  作者：Dana H. Braithwaite、CedricW. Holzapfel、D. Bradley G. Williams

  DOI：10.1039/a807128d

  日期：——

  Various glycals, treated with Tl(NO3)3·3H2O under mild conditions in an acetonitrile–methanol solvent mixture, underwent ring contraction in a stereoselective fashion, affording stable acetal products.

  在温和条件下，在乙腈-甲醇溶剂混合物中用Tl（NO 3）3 ·3H 2 O处理的各种糖，以立体选择性方式进行环收缩，得到稳定的乙缩醛产物。
• Highly stereoselective addition of organozinc reagents to pentopyranose derived glycals: effect of protecting group and assignment of C-glycoside stereochemistry
  作者：Matthew J Cook、Matthew J.E Fletcher、Diane Gray、Peter J Lovell、Timothy Gallagher

  DOI：10.1016/j.tet.2004.04.004

  日期：2004.5

  The nucleophilic addition of ethyl 3-propionylzinc iodide to a variety of differently protected pentopyranose derived d-glycals 6a–g proceeds with good to high levels of diastereoselectivity to provide the corresponding β-C-glycosides 7. The stereochemistry of the para-nitrobenzoate derivative 7d has been confirmed by X-ray crystallography, and the stereochemistry of the other β-C-glycoside products

  将3-丙酰碘化乙基乙酯亲核加成到各种受不同保护的戊吡喃糖衍生的d-糖6a - g上，具有很好的非对映选择性，提供了相应的β- C-糖苷7。所述的立体化学对-nitrobenzoate衍生物7D已通过X射线晶体学确认，其它β-的立体化学Ç糖苷产品已关联到7d的。观察到的立体化学结果支持了Isobe的早期建议，即通空效应对于稳定和控制11代表的中间氧鎓物种的反应性很重要。
• An efficient method for the synthesis of pyranoid glycals
  作者：Heshan Chen、Ting Xian、Wan Zhang、Wenshuai Si、Xiaosheng Luo、Bo Zhang、Meiyu Zhang、Zhongfu Wang、Jianbo Zhang

  DOI：10.1016/j.carres.2016.05.013

  日期：2016.8

  A simple and efficient procedure was designed for the preparation of pyranoid glycals. In a novel fashion, a series of protected glycopyranosyl bromides underwent reductive elimination in the presence of zinc dust and ammonium chloride in CH3CN at 30-60 °C. The corresponding glycals were obtained with excellent isolated yields (72-96%) in a short time (20-50 min). Furthermore, the transformation was

  设计了一种简单有效的方法来制备吡喃类糖。在30-60°C的条件下，在CH3CN中存在锌粉和氯化铵的情况下，以一系列新颖的方式对一系列受保护的吡喃葡萄糖基溴化物进行了还原消除。在短时间内（20-50分钟）以优异的分离产率（72-96％）获得了相应的糖。此外，该转化与不同的保护模式兼容且可方便地扩展（45 g乙酰溴葡萄糖为86％），使其非常适用于有机合成。
• Stereocontrolled halofluorination of glycals with silicon tetrafluoride, leading to a facile synthesis of glycosyl fluorides
  作者：Makoto Shimizu、Yuko Nakahara、Hirosuke Yoshioka

  DOI：10.1016/s0022-1139(99)00026-3

  日期：1999.7

  Bromofluorination of glycals was carried out with SiF4, 1,3-dibromo-5,5-dimethylhydantoin (DBH), and H2O in 1,4-dioxane in the presence of HMPA to give bromofluoro sugars in good yields with good selectivities. Subsequent debromination with n-Bu3SnH gave 2-deoxy sugars in good yields. Furthermore, hydroxyfluorination of glycal was also successfully conducted using SiF4-PhI(OAc)2-H2O to give fluoroglucose

  烯糖的Bromofluorination用的SiF进行4，1,3-二溴-5,5-二甲基海因（DBH），和H 2 ö在HMPA存在1,4-二恶烷，得到良好的收率与好的选择性bromofluoro糖。随后用n -Bu 3 SnH脱溴得到2-脱氧糖，收率良好。此外，还使用SiF 4 -PhI（OAc）2 -H 2 O成功地进行了糖基的羟基氟化，以73％的收率得到了氟葡萄糖。