(3aS,5R,6S,6aS)-5-(((叔丁基二苯基甲硅烷基)氧基)甲基)-2,2-二甲基四氢呋喃[2,3-d][1,3]二氧杂环戊烯-6-醇 | 133048-89-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (3aS,5R,6S,6aS)-5-(((叔丁基二苯基甲硅烷基)氧基)甲基)-2,2-二甲基四氢呋喃[2,3-d][1,3]二氧杂环戊烯-6-醇
• 英文名称: 5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-β-D-lyxofuranose
• 英文别名: (3aS,5R,6S,6aS)-5-(((tert-Butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol；(3aS,5R,6S,6aS)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 133048-89-2
• 化学式: C₂₄H₃₂O₅Si
• 分子量: 428.601
• InChiKey: XJKAZNSYWAGYDQ-MLNNCEHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30
• 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：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aS,5R,6S,6aS)-5-(((叔丁基二苯基甲硅烷基)氧基)甲基)-2,2-二甲基四氢呋喃[2,3-d][1,3]二氧杂环戊烯-6-醇 在 ammonium fluoride 作用下， 以 甲醇 为溶剂， 以84%的产率得到1,2-O-isopropylidene-β-D-lyxofuranose
  参考文献：
  名称：

  Deoxygenation at the C3 position of d- and l-arabinofuranose: stereospecific access to enantiomeric cordycepose derivatives

  摘要：

  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.

  DOI：

  10.1016/j.carres.2013.07.017
• 作为产物：
  描述：

  D-arabinose diethyl dithioacetal 在 咪唑 、 sodium tetrahydroborate 、 草酰氯 、 TEA 、 二甲基亚砜 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 (3aS,5R,6S,6aS)-5-(((叔丁基二苯基甲硅烷基)氧基)甲基)-2,2-二甲基四氢呋喃[2,3-d][1,3]二氧杂环戊烯-6-醇
  参考文献：
  名称：

  Elucidation of the 2- C -methyl- d -erythritol 4-phosphate pathway for isoprenoid biosynthesis: straightforward syntheses of enantiopure 1-deoxy- d -xylulose from pentose derivatives

  摘要：

  Optically pure I-deoxy-D-xylulose, a key metabolite for feeding experiments in the methylerythritol phosphate pathway for isoprenoid biosynthesis, is conveniently synthesised from 1,2-O-isopropylidene-alpha -D-xylofuranose or from D-arabinose. This renders labelling with hydrogen isotopes possible. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00376-8

文献信息

• [EN] A POSITRON EMISSION TOMOGRAPHY PROBE TO MONITOR SELECTED SUGAR METABOLISM IN VIVO<br/>[FR] SONDE DE TOMOGRAPHIE PAR ÉMISSION DE POSITRONS DESTINÉE À SURVEILLER LE MÉTABOLISME D'UN SUCRE SÉLECTIONNÉ IN VIVO
  申请人：UNIV CALIFORNIA

  公开号：WO2013170085A1

  公开（公告）日：2013-11-14

  The invention disclosed herein discloses selected ribose isomers that are useful as PET probes (e.g. [18F]-2-fluoro-2-deoxy-arabinose). These PET probes are useful, for example, in methods designed to monitor physiological processes including ribose metabolism and/or to selectively observe certain tissue/organs in vivo. The invention disclosed herein further provides methods for making and using such probes.

  本发明披露了选定的核糖异构体，这些异构体可用作PET探针（例如[18F]-2-氟-2-脱氧-阿拉伯糖）。这些PET探针可用于监测生理过程，包括核糖代谢，或者选择性地观察体内的某些组织/器官。本发明还提供了制备和使用这些探针的方法。
• A new synthesis of 3′‐deoxy‐3′‐fluoroadenosine, a key intermediate of cyclic dinucleotide
  作者：Yayun Qiu、Zixing Li、Fangmin Ning、Dandan Tang、Huansheng Chen

  DOI：10.1002/jhet.4751

  日期：2024.1

  A new synthesis of 3′-deoxy-3′-fluoroadenosine for use as an important intermediate of antitumor-active cyclic dinucleotide is disclosed. The synthesis started with the known 5-O-TBDPS-D-lyxofuranose 1,2-acetonides, which was first transformed into a fluorinated compound after the DAST reaction. Desilylation and acidic methanolysis were then finished in one pot. After a sequence of triflation, displacement

  公开了用作抗肿瘤活性环状二核苷酸的重要中间体的3'-脱氧-3'-氟腺苷的新合成。合成从已知的 5- O -TBDPS-D-呋喃来糖 1,2-丙酮化合物开始，在 DAST 反应后首先将其转化为氟化化合物。然后脱甲硅烷基化和酸性甲醇解在一锅中完成。经过一系列三氟甲磺酸化、OBz置换以及苯甲酰化，得到过苯甲酰化的3-脱氧-3-氟-D-呋喃核苷，将其转化为3'-脱氧-3'-氟腺苷，作为环状二核苷酸的关键中间体氨解后。
• Attempted ring contraction of α-triflates of 3-azido- and 3-fluoro-γ-lactones to oxetanes
  作者：R.P. Elliott、G.W.J. Fleet、K. Vogt、F.X. Wilson、Y. Wang、D.R. Witty、R. Storer、P.L. Myers、C.J. Wallis

  DOI：10.1016/s0957-4166(00)82381-2

  日期：1990.1
• Elucidation of the 2- C -methyl- d -erythritol 4-phosphate pathway for isoprenoid biosynthesis: straightforward syntheses of enantiopure 1-deoxy- d -xylulose from pentose derivatives
  作者：Jean-François Hoeffler、Catherine Grosdemange-Billiard、Michel Rohmer

  DOI：10.1016/s0040-4039(01)00376-8

  日期：2001.4

  Optically pure I-deoxy-D-xylulose, a key metabolite for feeding experiments in the methylerythritol phosphate pathway for isoprenoid biosynthesis, is conveniently synthesised from 1,2-O-isopropylidene-alpha -D-xylofuranose or from D-arabinose. This renders labelling with hydrogen isotopes possible. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.