1,3,4,6-tetra-O-benzoyl-D-fructofuranosyl acetate | 174848-29-4

• 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: 1,3,4,6-tetra-O-benzoyl-D-fructofuranosyl acetate
• 英文别名: 2-O-acetyl-1,3,4,6-tetra-O-benzoyl-d-fructofuranose；[(2R,3R,4S)-5-acetyloxy-3,4-dibenzoyloxy-5-(benzoyloxymethyl)oxolan-2-yl]methyl benzoate
• CAS: 174848-29-4
• 化学式: C₃₆H₃₀O₁₁
• 分子量: 638.628
• InChiKey: VMQSYJUFYPYXEC-WKNKJIQBSA-N

物化性质

• 沸点：
  728.0±60.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  47
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-benzoyl-D-fructofuranosyl acetate 在 三甲基氯硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以100 mg的产率得到1,3,4,6-tetra-O-benzoyl-D-fructofuranosyl chloride
  参考文献：
  名称：

  1-硫代蔗糖和端基异构体的合成，以及该底物类似物的蔗糖蔗糖酶和蔗糖酶的行为

  摘要：

  摘要Lewis酸催化2,3,4,6-四-O-乙酰基-1-硫代-α-d-吡喃葡萄糖与1,3,4,6-四-O-苄基-d-呋喃呋喃糖之间的缩合反应。二氯甲烷，然后LC分离脱保护的所得二糖，生成1-硫代蔗糖（β-d-果呋喃糖基1-硫代-α-d-吡喃葡萄糖苷）和α-d-果糖呋喃糖基1-硫代-α-d-葡糖吡喃糖苷，分别占总收益的15％和22％。类似地，2,3,4,6-四-O-乙酰基-1-硫代-β-d-吡喃葡萄糖与1,3,4,6-四-O-苄基-d-果糖呋喃糖反应，得到1以6：6的比例，将α-d-果呋喃糖基1-硫代-β-d-吡喃葡萄糖苷（1-硫代异蔗糖）及其β，β-异头物分离为它们的O-乙酰基衍生物。1-硫代蔗糖是枯草芽孢杆菌中蔗糖酶生物合成的诱导剂。

  DOI：

  10.1016/0008-6215(84)85287-8
• 作为产物：
  描述：

  乙酸酐 、 1,3,4,6-tetra-O-benzoyl-D-fructofuranose 在 2,4-二氨基嘧啶 作用下， 以 吡啶 为溶剂， 反应 18.0h， 以59%的产率得到1,3,4,6-tetra-O-benzoyl-D-fructofuranosyl acetate
  参考文献：
  名称：

  1-硫代蔗糖和端基异构体的合成，以及该底物类似物的蔗糖蔗糖酶和蔗糖酶的行为

  摘要：

  摘要Lewis酸催化2,3,4,6-四-O-乙酰基-1-硫代-α-d-吡喃葡萄糖与1,3,4,6-四-O-苄基-d-呋喃呋喃糖之间的缩合反应。二氯甲烷，然后LC分离脱保护的所得二糖，生成1-硫代蔗糖（β-d-果呋喃糖基1-硫代-α-d-吡喃葡萄糖苷）和α-d-果糖呋喃糖基1-硫代-α-d-葡糖吡喃糖苷，分别占总收益的15％和22％。类似地，2,3,4,6-四-O-乙酰基-1-硫代-β-d-吡喃葡萄糖与1,3,4,6-四-O-苄基-d-果糖呋喃糖反应，得到1以6：6的比例，将α-d-果呋喃糖基1-硫代-β-d-吡喃葡萄糖苷（1-硫代异蔗糖）及其β，β-异头物分离为它们的O-乙酰基衍生物。1-硫代蔗糖是枯草芽孢杆菌中蔗糖酶生物合成的诱导剂。

  DOI：

  10.1016/0008-6215(84)85287-8

文献信息

• Stereoselectivity of D-Psicofuranosylation Influenced by Protecting Groups of Psicofuranosyl Donors
  作者：Takashi Yamanoi、Yoshiki Oda、Toshiaki Ishiyama、Mikio Watanabe

  DOI：10.3987/com-15-s(t)39

  日期：——

  We synthesized several types of novel D-psicofuranosyl acetate derivatives, and investigated their use as glycosyl donors in scandium triflate-catalyzed D-psicofuranosylation reactions. Psicofuranosylation demonstrated unique stereoselectivities depending on the protecting groups of psicofuranosyl donors. The donor having a 3,4-isopropylidene group afforded beta-psicofuranosides with high stereoselectivities. Donors having a C3 benzoyloxy group demonstrated low stereoselectivities with no neighboring group participation. This study also discusses the stereoselectivities of psicofuranosylation based on the conformers of the glycosyl oxocarbenium ion intermediates as influenced by the protecting groups of the psicofuranosyl donors. We also compared the neighboring group participation of the glycosyl donors bearing a C3 benzoyloxy group during D-psicofuranosylation and D-fructofuranosylation.
• Synthesis and hybridization property of an oligonucleotide analog containing A 1′,3′-DI-O-methylene-α-D-fructose backbone
  作者：Ruiming Zou、Mark D. Matteucci

  DOI：10.1016/s0960-894x(98)00566-6

  日期：1998.11

  Hydrogen phosphonate monomers of T (thymine) and C-m (5-methylcytosine) bearing a 1',3'-di-O-methylene-alpha-D-fructose sugar moiety were synthesized and incorporated into an oligonucleotide. Hybridization studies by thermal denaturation experiment indicated that this oligonucleotide did not form a duplex with the complementary RNA target. (C) 1998 Elsevier Science Ltd. Ail rights reserved.
• A highly efficient d-fructofuranosylation catalyzed by scandium(III) triflate
  作者：Takashi Yamanoi、Noriko Misawa、Mikio Watanabe

  DOI：10.1016/j.tetlet.2007.07.092

  日期：2007.9

  This Letter describes a highly efficient D-fructofuranosylation catalyzed by scandium(III) triffate. The benzylated and benzoylated D-fructofuranosyl acetate derivatives worked as good reactive donors in the presence of only 5 mol % scandium(III) triflate at 0 degrees C in toluene to afford the D-fructofuranosides in excellent yields. The fructofuranosylation also produced several non-reducing disaccharides of sucrose mimics using several aldopyranose derivatives as the acceptors. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of <scp>d</scp>-Fructofuranosides Using Thioglycosides as Glycosyl Donors
  作者：Christian Krog-Jensen、Stefan Oscarson

  DOI：10.1021/jo951641t

  日期：1996.1.1

  Benzylated and benzoylated ethyl thioglycosides of D-fructofuranose have been synthesized and tested as glycosyl donors in couplings to various primary and secondary carbohydrate accepters. Treatment of 2-O-acetyl-1,3,4,6-tetra-O-benzoyl-D-fructofuranose with ethyl mercaptan in a BF3 .-etherate-promoted reaction gave the benzoylated ethyl 2-thio-alpha,beta-D-fructofuranosides, which after deacylation and benzylation afforded the benzylated derivatives. These thiofructofuranosides, using dimethyl(methylthio)sulfonium triflate (DMTST) or N-iodosuccinimide as promoter, were found to be excellent donors, which gave disaccharide coupling products in quantitative or almost quantitative yields with all tested accepters, yields rarely found in oligosaccharide synthesis. The benzoylated donors gave only alpha-linked fructofuranosides, due to participation of the 3-O-benzoyl group, whereas the benzylated donors gave alpha/beta-mixtures.