3-deoxy-2-C-hydroxymethyl-2,2'-O-isopropylidene-D-glycero-pentitol | 93662-50-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-2-C-hydroxymethyl-2,2'-O-isopropylidene-D-glycero-pentitol
• 英文别名: (2S)-3-[(4R)-4-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]propane-1,2-diol
• CAS: 93662-50-1
• 化学式: C₉H₁₈O₅
• 分子量: 206.239
• InChiKey: GMIRDBQPODKBHV-IONNQARKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-deoxy-2-C-hydroxymethyl-2,2'-O-isopropylidene-D-glycero-pentitol 在 4-二甲氨基吡啶 、 硫酸氢铵 、 sodium periodate 、 六甲基二硅氮烷 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 10.0h， 生成 1-[3-C-hydroxymethyl-3,3'-O-isopropylidene-α-L-glycero-tetrafuranosyl] uracil
  参考文献：
  名称：

  Synthesis of novel apionucleosides: a short and concise synthesis of 2-deoxyapio-l-furanosyl acetate from d-lactose

  摘要：

  A series of 2'-deoxyapio-L-furanosyl pyrimidine nucleosides were efficiently synthesized starting from D-lactose via condensation of lactitor acetates with silylated pyrimidine bases under standard Vorbruggen conditions. Their structures were determined by ID and 2D NMR spectroscopy. All the synthesized nucleosides were assayed against several viruses such as HIV-1, HBV, HSV-1, HSV-2, and HCMV. However, none of these compounds had any significant antiviral activity at concentrations up to 100 muM. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00018-1
• 作为产物：
  描述：

  3-deoxy-2-C-hydroxymethyl-D-erythro-pentono-1,4-lactone 在 lithium aluminium tetrahydride 作用下， 生成 3-deoxy-2-C-hydroxymethyl-2,2'-O-isopropylidene-D-glycero-pentitol
  参考文献：
  名称：

  光学活性的4-脱甲氧基蒽环素的有效合成

  摘要：

  由乳糖作为环A的手性前体和由亮氨酸喹嗪碱作为环B，C和D的前体，只需几步即可合成旋光的4-de甲氧基蒽环素。

  DOI：

  10.1016/0040-4039(84)80044-1

文献信息

• An efficient synthesis of optically active 4-demethoxy anthracyclinones
  作者：Fatima Bennani、Jean-Claude Florent、Michel Koch、Claude Monneret

  DOI：10.1016/s0040-4020(01)91528-5

  日期：1984.1

  Optically active 4-demethoxy-anthracyclinones related to daunorubicin were synthesized in several steps from lactose as chiral precursor of ring A and from leucoquinizarine as precursor of rings B, C and D.

  分几步合成了与柔红霉素有关的旋光性4-脱甲氧基蒽环酮，其中乳糖作为环A的手性前体，而白藜芦碱则作为环B，C和D的前体。
• Synthesis of Enantiomerically Pure Heterocycles: Access to Hydroxylated Piperidines from a Sugar Lactone
  作者：Christine Thomassigny、Khalil Bennis、Jacques Gelas

  DOI：10.1055/s-1997-1167

  日期：1997.2

  A protected hydroxylated piperidine 7 and its bicyclo- and substituted diastereoisomers 12 and 13, respectively, have been synthesizes from α-D-isosaccharino-1,4-lactone (3), in two very short sequences.

  受保护的羟基化哌啶 7 及其双环和取代的非对映异构体 12 和 13 分别由 α-D-异糖精-1,4-内酯 (3) 以两个非常短的序列合成。
• Anthracyclinones. 2. Isosaccharinic acid as chiral template for the synthesis of (+)-4-demethoxy-9-deacetyl-9-hydroxymethyldaunomycinone and (-)-4-deoxy-.gamma.-rhodomycinone
  作者：J. C. Florent、J. Ughetto-Monfrin、Claude Monneret

  DOI：10.1021/jo00382a015

  日期：1987.3
• FLORENT, J. -C.;MONNERET, C.
  作者：FLORENT, J. -C.、MONNERET, C.

  DOI：——

  日期：——
• Synthesis of novel apionucleosides: a short and concise synthesis of 2-deoxyapio-l-furanosyl acetate from d-lactose
  作者：Jihee Kim、Joon Hee Hong

  DOI：10.1016/s0008-6215(03)00018-1

  日期：2003.4

  A series of 2'-deoxyapio-L-furanosyl pyrimidine nucleosides were efficiently synthesized starting from D-lactose via condensation of lactitor acetates with silylated pyrimidine bases under standard Vorbruggen conditions. Their structures were determined by ID and 2D NMR spectroscopy. All the synthesized nucleosides were assayed against several viruses such as HIV-1, HBV, HSV-1, HSV-2, and HCMV. However, none of these compounds had any significant antiviral activity at concentrations up to 100 muM. (C) 2003 Elsevier Science Ltd. All rights reserved.