3,4-di-O-benzoyl-D-olivosyl fluoride | 128461-94-9

• 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: 3,4-di-O-benzoyl-D-olivosyl fluoride
• 英文别名: 3,4-di-O-benzoyl-2,6-dideoxy-α-D-arabinopyranosyl fluoride；[(2R,3R,4R,6R)-3-benzoyloxy-6-fluoro-2-methyloxan-4-yl] benzoate
• CAS: 128461-94-9
• 化学式: C₂₀H₁₉FO₅
• 分子量: 358.366
• InChiKey: CTFDXFVVMWNUIM-NKGKWGDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3,4-di-O-benzoyl-D-olivosyl fluoride 在 二氯二茂铪 、 4 A molecular sieve 、 silver perchlorate 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.83h， 生成 [(2R,3R,4R,6R)-3-benzoyloxy-2-methyl-6-(1,5,9,10-tetramethoxyanthracen-2-yl)oxan-4-yl] benzoate
  参考文献：
  名称：

  Convergent total synthesis of vineomycinone B2 methyl ester and its C(12)-epimer

  摘要：

  Total syntheses of vineomycinone B2 methyl ester (7) and its C(12)-epimer (epi-7) have been completed. The key reaction for construction of the aryl C-glycoside linkage is the O --> C-glycoside rearrangement starting from D-olivosyl fluoride derivative 11 and anthrol derivative 21, which provides the regio- and stereocontrolled formation of the aryl C-glycoside sector of the target. The combination of Cp2HfCl2-AgClO4 serves as a particularly efficient promoter for this reaction. An extensive model study for attaching the side chain is presented. The Lochmann-Schlosser base cleanly effects ortho metalation of anthracene derivatives 19 and 20. The metalated species can be trapped as stannyl derivatives, from which the corresponding aryllithium species are generated by using n-BuLi or preferably MeLi in toluene. These specific reaction conditions are necessary to suppress the abnormal reaction of RLi reagents at the C(9)/C(10)-positions of the anthracenes. Coupling of the side chain moiety was efficiently carried out by such metalation of anthracene derivative 25 followed by reaction with chiral aldehyde (S)-29. The chiral aldehyde was derived from enantiomerically pure acid (S)-37 obtained by enzymatic kinetic resolution. Deoxygenation of the benzylic alcohol function followed by several steps allowed the total ynthesis of 7. Starting from (R)-aldehyde 29, the same sequence of reactions accomplished the total synthesis of epi-7. The epi series of intermediates provided firm evidence for the stereochemical homogeneity of synthetic 7.

  DOI：

  10.1021/ja00018a041
• 作为产物：
  描述：

  methyl 3,4-di-O-benzoyl-2,6-dideoxy-α-D-arabino-hexopyranoside 在 盐酸 、 氟化氢吡啶 、 溶剂黄146 作用下， 以 吡啶 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 生成 3,4-di-O-benzoyl-D-olivosyl fluoride
  参考文献：
  名称：

  Synthetic study toward vineomycins. Synthesis of c-aryl glycoside sector via Cp2HfCl2AgClO4-promoted tactics

  摘要：

  DOI：

  10.1016/s0040-4039(01)93337-4

文献信息

• 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。
• MATSUMOTO, TAKASHI;KATSUKI, MIYOKO;JONA, HIDEKI;SUZUKI, KEISUKE, TETRAHEDRON LETT., 30,(1989) N5, C. 6185-6189
  作者：MATSUMOTO, TAKASHI、KATSUKI, MIYOKO、JONA, HIDEKI、SUZUKI, KEISUKE

  DOI：——

  日期：——