5-deoxy-1,2-O-isopropylidene-6-O-triphenylmethyl-α-D-xylohexofuranose | 37070-23-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5-deoxy-1,2-O-isopropylidene-6-O-triphenylmethyl-α-D-xylohexofuranose
• 英文别名: 5-deoxy-1,2-O-isopropylidene-6-O-trityl-α-D-xylo-hexofuranose；(3aR,5R,6S,6aR)-2,2-dimethyl-5-(2-trityloxyethyl)-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 37070-23-8
• 化学式: C₂₈H₃₀O₅
• 分子量: 446.543
• InChiKey: KRIVCODVYFXDCT-XDZVQPMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-deoxy-1,2-O-isopropylidene-6-O-triphenylmethyl-α-D-xylohexofuranose 在 sodium tetrahydroborate 、 3 A molecular sieve 、 Amberlite IR-120 (H+) 、 sodium acetate 、 pyridinium chlorochromate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 27.0h， 生成 5-deoxy-D-ribo-hexofuranose
  参考文献：
  名称：

  Synthetic applications of glucose isomerase: isomerisation of C-5-modified (2R,3R,4R)-configured hexoses into the corresponding 2-ketoses

  摘要：

  Immobilised glucose isomerase (EC 5.3.1.5) accepted various (2R,3R,4R)-configured hexoses such as 5-deoxy-D-ribo-hexose, 5-azido-5-deoxy-D-allose, as well as the corresponding epimer at C-5, 5-azido-5-deoxy-L-talose, as substrates. From the resulting azidodeoxyketoses, 5-azido-5-deoxy-D-psico- and -L-tagatopyranose, the powerful D-galactosidase inhibitors 2,5-dideoxy-2,5-imino-D-galactital and -D-altritol were obtained in one additional step. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00119-6
• 作为产物：
  描述：

  1,2-O-Isopropyliden-6-O-triphenylmethyl-5-desoxy-α-D-xylo-hexofuran-5-enose 在 sodium tetrahydroborate 、 sodium methylate 、 溶剂黄146 、 三乙胺 作用下， 以 1,4-二氧六环 、 吡啶 、 甲醇 、 乙醇 、 水 为溶剂， 反应 26.5h， 生成 5-deoxy-1,2-O-isopropylidene-6-O-triphenylmethyl-α-D-xylohexofuranose
  参考文献：
  名称：

  Mikhailov, Sergei N.; Padyukova, Nelly Sh.; Karpeiskii, Marat Ya., Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 4, p. 1055 - 1066

  摘要：

  DOI：

文献信息

• Efficient Divergent Synthesis of 2′-<i>O</i>,4′-<i>C</i>-Ethylene-Bridged Nucleic Acid (ENA) Phosphoramidites
  作者：Yuzo Abe、Kazutoshi Ukai、Makoto Michida

  DOI：10.1021/acs.oprd.2c00013

  日期：2022.4.15

  developed a highly efficient synthetic method for ENA phosphoramidites. The basic concept of the new synthetic route is “divergent synthesis” for the preparation of four types of monomers such as A, G, C, and T. We applied stereoselective glycosylation reactions without utilizing neighboring group participation to set a common intermediate in the downstream of the route.

  2'- O ,4'- C-乙烯桥连核酸（ENA）亚磷酰胺是第一三共发现的极具前景的修饰核酸单体。为了提高生产效率，我们开发了一种高效的 ENA 亚磷酰胺合成方法。新合成路线的基本概念是“发散合成”，用于制备 A、G、C 和 T 四种单体。我们应用立体选择性糖基化反应，不利用相邻基团参与，在下游设置共同的中间体的路线。
• A new scheme for the synthesis of 5′-nucleotide phosphonate analogs
  作者：Nelly Sh Padyukova、Marat Ya Karpeisky、Lidiya I Kolobushkina、Sergey N Mikhailov

  DOI：10.1016/s0040-4039(00)95552-7

  日期：1987.1

  A convenient and general method is proposed for the synthesis of 5′-nucleotide phosphonate analogs starting from 5-deoxy-1,2-O-isopropylidene- α-D-xylo-hexofuranose (1).

  提出了一种方便且通用的方法，以5-脱氧-1,2-O-异亚丙基-α-D-木糖六呋喃糖为原料合成5'-核苷酸膦酸酯类似物（1）。
• Synthesis of 5,6-dimodified open-chain d-fructose derivatives and their properties as substrates of bacterial polyol dehydrogenase
  作者：Philipp Hadwiger、Peter Mayr、Bernd Nidetzky、Arnold E Stütz、Andreas Tauss

  DOI：10.1016/s0957-4166(99)00526-1

  日期：2000.2

  5-Deoxy-5-fluoro-D-xylulose as well as a range of new 5,6-dimodifed open-chain analogues of D-fructose, namely the 5,6-diazido-5,6-dideoxy, 6-azido-5,6-dideoxy, 6-azido-5,6-dideoxy-5-fluoro, 5,6-dideoxy-5-fluoro, 5,6-dideoxy-6-fluoro and 5,6-dideoxy-5,6-difluoro derivatives, were synthesised employing glucose isomerase catalysed isomerisation of the corresponding D-xylo- and D-glucofuranoses as a key step. New compounds as well as some previously reported analogues such as 5-azido-5,6-dideoxy-6-fluoro-D- fructose were shown to be excellent substrates of polyol dehydrogenase from Burkholderia cepacia DSM 50181 with K-m values two orders of magnitude smaller than the corresponding natural substrates. (C) 2000 Elsevier Science Ltd, All rights reserved.
• Binding and catalysis by yeast aldose reductase: A substrate-analog approach with new aldose derivatives
  作者：Philipp Hadwiger、Peter Mayr、Andreas Tauss、Arnold E Stütz、Bernd Nidetzky

  DOI：10.1016/s0960-894x(99)00255-3

  日期：1999.6

  5-Deoxy-D-xylofuranose derivatives and a range of new 5,6-dideoxy analogs of D-glucofuranose bearing azido or fluoro substituents were synthesised and employed as substrates of the NADH-dependent aldehyde reduction catalysed by yeast aldose reductase. In terms of catalytic efficiencies, these products proved to be superior to the parent compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.
• MIKHAILOV, SERGEI N.;PADYUKOVA, NELLY SH.;KARPEISKII, MARAT YA.;KOLOBUSHK+, COLLECT. CZECHOSL. CHEM. COMMUN., 54,(1989) N, C. 1055-1066
  作者：MIKHAILOV, SERGEI N.、PADYUKOVA, NELLY SH.、KARPEISKII, MARAT YA.、KOLOBUSHK+

  DOI：——

  日期：——