5-O-(tert-butyldiphenylsilyl)-3-deoxy-1,2-O-isopropylidene-β-L-treopentofuranose | 150950-21-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-O-(tert-butyldiphenylsilyl)-3-deoxy-1,2-O-isopropylidene-β-L-treopentofuranose
• 英文别名: 5-O-tert-butyldiphenylsilyl-3-deoxy-1,2-O-isopropylidene-β-L-threo-pentofuranose；[(3aR,5R,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methoxy-tert-butyl-diphenylsilane
• CAS: 150950-21-3
• 化学式: C₂₄H₃₂O₄Si
• 分子量: 412.601
• InChiKey: YBYPDGJMQGKASW-STZQEDGTSA-N

物化性质

• 沸点：
  451.0±38.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-O-(tert-butyldiphenylsilyl)-3-deoxy-1,2-O-isopropylidene-β-L-treopentofuranose 在 四氯化碳 、 磷酸酐 、 sodium tetrahydroborate 、 sodium periodate 、 溶剂黄146 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 32.08h， 生成 (R)-1-((tert-butyldiphenylsilyl)oxy)-4-chloro-2-(methoxymethoxy)butane
  参考文献：
  名称：

  An Enantiospecific Synthesis of the Human Cytomegalovirus Antiviral Agent [(R)-3-((2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4- hydroxybutyl]phosphonic Acid

  摘要：

  The racemic isosteric phosphonate of ganciclovir monophosphate (BW2482U89, SR3745, [3-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4-hydroxybutyl]phosphonic acid, 1) has potent and selective in vitro;activity against human cytomegalovirus. An enantiospecific synthesis of the R-enantiomer of compound 1 starting from L-arabinose was developed. The synthesis involved (1) the preparation of a chiral acyclic moiety, (2) the coupling of the chiral acyclic moiety to diacetylguanine, (3) the introduction; of phosphorus, and (4) the final deprotection. The R-enantiomer, which has stereochemistry analogous to the natural compound GMP, was tested against human cytomegalovirus and had an IC50 Of 1.7 mu M, which was approximately 2-fold more active than the racemic material. Both racemic and chiral compounds were less toxic than ganciclovir to bone marrow progenitor cells in an in vitro assay.

  DOI：

  10.1021/jm00035a018
• 作为产物：
  描述：

  Dithiocarbonic acid O-[(3aR,5S,6S,6aR)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl] ester S-methyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以84%的产率得到5-O-(tert-butyldiphenylsilyl)-3-deoxy-1,2-O-isopropylidene-β-L-treopentofuranose
  参考文献：
  名称：

  基于碳水化合物的天然存在的海洋代谢产物slagenins B和C的合成。

  摘要：

  [反应：见正文]已经描述了Slagenins B和C（来自Agelas nakamurai的海洋代谢产物）从L-阿拉伯糖开始的第一对映选择性合成。

  DOI：

  10.1021/ol020112q

文献信息

• Deoxygenation at the C3 position of d- and l-arabinofuranose: stereospecific access to enantiomeric cordycepose derivatives
  作者：Fábio da Paixão Soares、Maria Joselice e Silva、Bogdan Doboszewski

  DOI：10.1016/j.carres.2013.07.017

  日期：2013.10

  Efficient synthesis of 3-deoxy-1,2-O-isopropylidene-beta-D- and beta-L-threo-pentofuranose (1,2-O-isopropylidene-beta-D- and beta-L-cordycepose) was accomplished starting from D- and L-arabinofuranose derivatives, respectively, by the action of LiBH(Et)(3) on corresponding intermediate 3-O-lyxofuranosyl trifluoromethanesulfonates. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.
• Carbohydrate-Based Synthesis of Naturally Occurring Marine Metabolites Slagenins B and C
  作者：Mukund K. Gurjar、Smritilekha Bera

  DOI：10.1021/ol020112q

  日期：2002.10.1

  [reaction: see text] The first enantioselective syntheses of slagenins B and C, marine metabolites from Agelas nakamurai, starting from L-arabinose have been described.

  [反应：见正文]已经描述了Slagenins B和C（来自Agelas nakamurai的海洋代谢产物）从L-阿拉伯糖开始的第一对映选择性合成。
• An Enantiospecific Synthesis of the Human Cytomegalovirus Antiviral Agent [(R)-3-((2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4- hydroxybutyl]phosphonic Acid
  作者：Stanley D. Chamberlain、Karen K. Biron、Ronna E. Dornsife、Devron R. Averett、Lilia Beauchamp、George W. Koszalka

  DOI：10.1021/jm00035a018

  日期：1994.4

  The racemic isosteric phosphonate of ganciclovir monophosphate (BW2482U89, SR3745, [3-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)-4-hydroxybutyl]phosphonic acid, 1) has potent and selective in vitro;activity against human cytomegalovirus. An enantiospecific synthesis of the R-enantiomer of compound 1 starting from L-arabinose was developed. The synthesis involved (1) the preparation of a chiral acyclic moiety, (2) the coupling of the chiral acyclic moiety to diacetylguanine, (3) the introduction; of phosphorus, and (4) the final deprotection. The R-enantiomer, which has stereochemistry analogous to the natural compound GMP, was tested against human cytomegalovirus and had an IC50 Of 1.7 mu M, which was approximately 2-fold more active than the racemic material. Both racemic and chiral compounds were less toxic than ganciclovir to bone marrow progenitor cells in an in vitro assay.