[(4'S,5'S)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methanol | 100906-46-5

• 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: [(4'S,5'S)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methanol
• 英文别名: [(4S,5S)-2,2-dimethyl-5-phenylmethoxy-1,3-dioxan-4-yl]methanol
• CAS: 100906-46-5
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: XLECRIILTOJASF-STQMWFEESA-N

物化性质

• 熔点：
  60-62 °C
• 沸点：
  359.5±32.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(4'S,5'S)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methanol 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 四丁基碘化铵 、 sodium hydride 、 二异丁基氢化铝 、 potassium carbonate 、 对甲苯磺酸 、 臭氧 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 邻二甲苯 、 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 、 mineral oil 为溶剂， 反应 39.83h， 生成 (4R)-3-benzyl-4-[(1'S,2'S)-1',2'-bis(benzyloxy)-3'-hydroxypropyl]oxazolidin-2-one
  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：

  3-O-benzyl-1,2-O-isopropylidene-5-O-trityl-β-L-lyxofuranose 在 吡啶 、 甲醇 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 乙醇 、 D(+)-10-樟脑磺酸 、 水 、 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 18.59h， 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

文献信息

• Total synthesis of mycestericin A and its 14-epimer
  作者：Hiroyoshi Yamanaka、Kazuya Sato、Hideyuki Sato、Masatoshi Iida、Takeshi Oishi、Noritaka Chida

  DOI：10.1016/j.tet.2009.09.012

  日期：2009.11

  The total synthesis of mycestericin A (1) and its 14-epimer 34 is described herein. The Overman rearrangement of an allylic trichloroacetimidate derived from l-tartrate generated a tetra-substituted carbon with nitrogen and subsequent stereoselective transformations afforded the highly functionalized left-half segment, vinyl iodide. Cross-coupling of the vinyl iodide with a chiral organometallic species

  本文描述了mycestericin A（1）及其14-受体34的总合成。衍生自1-酒石酸酯的烯丙基三氯乙酰亚胺酸酯的超载重排产生了具有氮的四取代碳，随后的立体选择性转化提供了高度官能化的左半段碘乙烯。在Negishi或Suzuki-Miyaura偶联条件下，碘化乙烯与d-酒石酸合成的手性有机金属物质交叉偶联，然后脱保护，完成了1的总合成。还合成了Mycestericin A的14个表位，并比较了[α] D霉菌素A及其14-受体的过乙酰基γ-内酯衍生物的分子量值以及对1和34的降解研究充分证实了拟议的霉菌素A的绝对结构。
• The use of l-tartaric acid in the synthesis of enanthiomerically pure compounds: synthesis of 4-O-benzyl-2,3-dideoxi-L- threo-hex-2-en no-1,5-lactone.
  作者：Serafin Valverde、Bernardo Herradon、M. Martin-Lomas

  DOI：10.1016/s0040-4039(00)89235-7

  日期：1985.1
• Total synthesis of mycestericin A
  作者：Hideyuki Sato、Kazuya Sato、Masatoshi Iida、Hiroyoshi Yamanaka、Takeshi Oishi、Noritaka Chida

  DOI：10.1016/j.tetlet.2008.01.105

  日期：2008.3

  The first total synthesis of mycestericin A (1) starting from tartrates is described. The Overman rearrangement of an allylic trichloroacetimidate generated a tetra-substituted carbon with nitrogen, and subsequent stereoselective transformations afforded the highly functionalized vinyl iodide. The cross-coupling of the vinyl iodide with a chiral organozinc species under Negishi conditions, followed by deprotection, completed the total synthesis of 1. (c) 2008 Elsevier Ltd. All rights reserved.