3-O-benzyl-1,2-O-isopropylidene-β-L-lyxofuranose

• 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-O-benzyl-1,2-O-isopropylidene-β-L-lyxofuranose
• 英文别名: 3-O-Benzyl-1,2-O-isopropylidene-B-L-lyxofuranose；[(3aR,5S,6R,6aR)-2,2-dimethyl-6-phenylmethoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methanol
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: ACGQAKYHAOEVJI-REWJHTLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-O-benzyl-1,2-O-isopropylidene-β-L-lyxofuranose 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 potassium carbonate 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 13.08h， 生成 [(4'S,5'S)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methanol
  参考文献：
  名称：

  Total synthesis of pachastrissamine together with its 4-epi-congener via [3,3]-sigmatropic rearrangements and antiproliferative/cytotoxic evaluation

  摘要：

  Synthesis of the HCl salts of two anhydrophytosphingosines, jaspine B (1) and its 4-epi-congener 5 from easily available dimethyl L-tartrate and/or L-arabinose, is described. The key transformations are the efficient incorporation of a chiral amino group via [3,3]-sigmatropic rearrangements, a Wittig olefination for the instalment of the carbon backbone and the acid-promoted building-up of a tetrahydrofuran framework. Evaluation for in vitro antiproliferative/cytotoxic activity with a panel of human tumour cell lines using a MTT assay revealed for some compounds of our strategy noteworthy activity. Compound 1 center dot HCl (IC50: 0. 41-2.35 mu M), its antipode ent-1 center dot HCl (IC50: 4.07-5.69 mu M) and also stereoisomer 4 center dot HCl (IC50: 4.28-6.10 mu M) exhibited significant potency compared with clinically available anticancer drugs such as cisplatin (IC(5)0: 11.4-14.7 mu M) and etoposide (IC50: 1.2-21.2 mu M) on MDA-MB-231, MCF-7 and Jurkat cells. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.11.004
• 作为产物：
  描述：

  L-阿拉伯糖 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 camphor-10-sulfonic acid 、 四丁基碘化铵 、 sodium hydride 、 2-碘酰基苯甲酸 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 、 mineral oil 为溶剂， 反应 79.17h， 生成 3-O-benzyl-1,2-O-isopropylidene-β-L-lyxofuranose
  参考文献：
  名称：

  Total synthesis of pachastrissamine together with its 4-epi-congener via [3,3]-sigmatropic rearrangements and antiproliferative/cytotoxic evaluation

  摘要：

  Synthesis of the HCl salts of two anhydrophytosphingosines, jaspine B (1) and its 4-epi-congener 5 from easily available dimethyl L-tartrate and/or L-arabinose, is described. The key transformations are the efficient incorporation of a chiral amino group via [3,3]-sigmatropic rearrangements, a Wittig olefination for the instalment of the carbon backbone and the acid-promoted building-up of a tetrahydrofuran framework. Evaluation for in vitro antiproliferative/cytotoxic activity with a panel of human tumour cell lines using a MTT assay revealed for some compounds of our strategy noteworthy activity. Compound 1 center dot HCl (IC50: 0. 41-2.35 mu M), its antipode ent-1 center dot HCl (IC50: 4.07-5.69 mu M) and also stereoisomer 4 center dot HCl (IC50: 4.28-6.10 mu M) exhibited significant potency compared with clinically available anticancer drugs such as cisplatin (IC(5)0: 11.4-14.7 mu M) and etoposide (IC50: 1.2-21.2 mu M) on MDA-MB-231, MCF-7 and Jurkat cells. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.11.004

文献信息

• Total synthesis of pachastrissamine together with its 4-epi-congener via [3,3]-sigmatropic rearrangements and antiproliferative/cytotoxic evaluation
  作者：Miroslava Martinková、Eva Mezeiová、Milica Fabišíková、Jozef Gonda、Martina Pilátová、Ján Mojžiš

  DOI：10.1016/j.carres.2014.11.004

  日期：2015.1

  Synthesis of the HCl salts of two anhydrophytosphingosines, jaspine B (1) and its 4-epi-congener 5 from easily available dimethyl L-tartrate and/or L-arabinose, is described. The key transformations are the efficient incorporation of a chiral amino group via [3,3]-sigmatropic rearrangements, a Wittig olefination for the instalment of the carbon backbone and the acid-promoted building-up of a tetrahydrofuran framework. Evaluation for in vitro antiproliferative/cytotoxic activity with a panel of human tumour cell lines using a MTT assay revealed for some compounds of our strategy noteworthy activity. Compound 1 center dot HCl (IC50: 0. 41-2.35 mu M), its antipode ent-1 center dot HCl (IC50: 4.07-5.69 mu M) and also stereoisomer 4 center dot HCl (IC50: 4.28-6.10 mu M) exhibited significant potency compared with clinically available anticancer drugs such as cisplatin (IC(5)0: 11.4-14.7 mu M) and etoposide (IC50: 1.2-21.2 mu M) on MDA-MB-231, MCF-7 and Jurkat cells. (C) 2014 Elsevier Ltd. All rights reserved.