5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-threo-pentofuranose-3-ulose | 103763-15-1

• 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-1,2-O-isopropylidene-β-L-threo-pentofuranose-3-ulose
• 英文别名: (3aR,5S,6aS)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-3a,6a-dihydrofuro[2,3-d][1,3]dioxol-6-one
• CAS: 103763-15-1
• 化学式: C₂₄H₃₀O₅Si
• 分子量: 426.585
• InChiKey: LVVPFDIKDGCSOA-KSEOMHKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-threo-pentofuranose-3-ulose 在 吡啶 、 sodium tetrahydroborate 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.09h， 生成 5-O-(tert-butyldiphenylsilyl)-3-deoxy-1,2-O-isopropylidene-β-L-treopentofuranose
  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：

  阿拉伯糖 在 吡啶 、 咪唑 、 chromium(VI) oxide 、 硫酸 、 copper(II) sulfate 作用下， 以 二氯甲烷 、 乙酸酐 为溶剂， 反应 19.17h， 生成 5-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-β-L-threo-pentofuranose-3-ulose
  参考文献：
  名称：

  Dahlman; Garegg; Mayer, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 1, p. 15 - 20

  摘要：

  DOI：

文献信息

• Synthesis of spiro carbon linked disaccharides from d-glucose, d- and l-arabinose
  作者：G.V.M Sharma、V.Goverdhan Reddy、Palakodety Radha Krishna、A.Ravi Sankar、A.C Kunwar

  DOI：10.1016/s0040-4020(02)00319-8

  日期：2002.5

  The synthesis of new spiro carbon linked disaccharides from d-glucose, d- and l-arabinose is described. In the present study furan is used as a masked sugar synthon, while chirality is transferred from the sugar derived chiral templates.

  描述了由d-葡萄糖，d-和1-阿拉伯糖合成新的螺碳连接的二糖。在本研究中，呋喃用作掩蔽的糖合成子，而手性则从糖衍生的手性模板转移而来。
• Carbohydrate-based approach to four enantiomerically pure 2-naphthylmethyl 3-hydroxy-2-methylbutanoates
  作者：Bogdan Doboszewski、Piet Herdewijn

  DOI：10.1016/j.tetlet.2007.12.104

  日期：2008.2

  Chiral pool approach using d-glucose, l-xylose, and d- and l-arabinoses was used to obtain four stereoisomeric 3-hydroxy-2-methylbutanoic acids with well defined configurations. The acids were isolated as fluorescent 2-naphthylmethyl esters after reaction with 2-naphthyldiazomethane.

  使用d-葡萄糖，l-木糖以及d-和l-阿拉伯糖的手性库法获得了具有明确定义构型的四种立体异构体3-羟基-2-甲基丁酸。与2-萘基重氮甲烷反应后，分离出作为荧光的2-萘基甲基酯的酸。
• Dimerization of aldosuloses and aldonolactones into branched higher carbon sugars
  作者：Yachen Zhao、Shengyang Wang、Biao Yu

  DOI：10.1039/c9cc09093b

  日期：——

  Homo-dimerizations of a variety of aldosulose and aldonolactone derivatives via aldol and Claisen reactions have been achieved, leading to novel branched higher carbon sugars in a highly stereoselective manner.

  已经通过醛醇缩合反应和克莱森反应实现了多种醛糖和醛糖内酯衍生物的均二聚，从而以高度立体选择性的方式产生了新的支链高碳糖。
• Amipurimycin: Total Synthesis of the Proposed Structures and Diastereoisomers
  作者：Shengyang Wang、Jiansong Sun、Qingju Zhang、Xin Cao、Yachen Zhao、Gongli Tang、Biao Yu

  DOI：10.1002/anie.201800169

  日期：2018.3.5

  The proposed diastereoisomers (1 a–d) together with their C8′‐epimers (1 e–h) of amipurimycin, a unique antifungal peptidyl nucleoside antibiotic, have been synthesized for the first time. The synthetic approach is efficient and stereodivergent, and features a stereoselective aldol condensation to build the branched C9 sugar amino acid skeleton and a regio‐ and stereocontrolled gold(I)‐catalyzed N‐glycosylation

  拟议的非对映异构体（1 a – d）以及其独特的抗真菌肽基肽核苷抗生素Amipurimycin的C8'-顶基（1 e – h）首次合成。合成方法高效且立体发散，并具有立体选择性羟醛缩合以构建分支的C9糖氨基酸骨架，以及区域和立体控制的金（I）催化的N-糖基化作用，以提供嘌呤核苷。NMR数据分析表明，阿米普霉素中先前分配的叔C3'构型应为相反构型。
• Branched-chain nucleosides: Synthesis of 3′-deoxy-3′-C- hydroxymethyl-α-l-lyxopyranosyl thymine and 3′-deoxy- 3′-C-hydroxymethyl-α-l-threofuranosyl thymine.
  作者：Bogdan Doboszewski、Piet Herdewijn

  DOI：10.1016/0040-4020(95)00994-9

  日期：1996.1

  The synthesis of 3′-deoxy-3′-C-hydroxymethyl branched nucleosides with α- l-lyxopyranosyl and α-l-threofuranosyl sugar moleties is described. The synthetic scheme makes use of a furanose → pyranose conversion and of the formation of both furanose and pyranose nucleosides during Vörbruggen sugar-base condensation reaction starting from tetra-O-acetyl-3-deoxy-3-C-hydroxymethyl-l-lyxo-(1,6)-furanose.

  描述了具有α-1-Ly-吡喃吡喃糖基和α-1-L-呋喃呋喃糖基糖摩尔的3'-脱氧-3'- C-羟甲基支链核苷的合成。该合成方案利用了呋喃糖→吡喃糖的转化，并在Vörbruggen糖基缩合反应中从四-O-乙酰基-3-脱氧-3- C-羟甲基-1-Lyxo-开始，形成了呋喃糖和吡喃糖核苷。（1,6）-呋喃糖。讨论了靶分子的构象