1,2-dideoxy-4,6-O-isopropylidene-3-O-methyl-D-arabino-hex-1-enopyranose | 72727-02-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 1,2-dideoxy-4,6-O-isopropylidene-3-O-methyl-D-arabino-hex-1-enopyranose
• 英文别名: (4aR,8R,8aS)-8-methoxy-2,2-dimethyl-4,4a,8,8a-tetrahydropyrano[3,2-d][1,3]dioxine
• CAS: 72727-02-7
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: GQAACYWZOYQYJS-HLTSFMKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  1,2-dideoxy-4,6-O-isopropylidene-3-O-methyl-D-arabino-hex-1-enopyranose 在 甲醇 、 对甲苯磺酸 、 三氟乙酸酐 作用下， 以 二甲基亚砜 、 丙酮 为溶剂， 生成 1-cyano-3,4-dihydro-3(S*)-(1-methoxy-3,4-O-isopropylidene-2-oxybutyl)naphthalene
  参考文献：
  名称：

  Stereocontrolled synthesis of a model aureolic acid aglycone via Diels-Alder reaction of an unsaturated sugar

  摘要：

  DOI：

  10.1021/jo01294a055
• 作为产物：
  描述：

  4,6-O-异亚丙基-D-葡萄糖醛 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.33h， 以81%的产率得到1,2-dideoxy-4,6-O-isopropylidene-3-O-methyl-D-arabino-hex-1-enopyranose
  参考文献：
  名称：

  Total synthesis of (+)-papulacandin D

  摘要：

  A total synthesis of (+)-papulacandin D has been achieved in 31 steps, in a 9.2% overall yield from commercially available materials. The synthetic strategy divided the molecule into two nearly equal sized subunits, the spirocyclic C-arylglycopyranoside and the polyunsaturated fatty acid side-chain. The C-arylglycopyranoside was prepared in 11 steps in a 30% overall yield from triacetoxyglucal. The fatty acid side-chain was also prepared in 11 steps in a 30% overall yield from geraniol. The key strategic transformations in the synthesis are: (1) a palladium-catalyzed, organosilanolate-based cross-coupling reaction of a dimethylglucal-silanol with an electron-rich and sterically hindered aromatic iodide and (2) a Lewis-base catalyzed, enantioselective allylation reaction of a dienal and allyltrichlorosilane. A critical element in the successful execution of the synthesis was the development of a suitable protecting group strategy that satisfied a number of stringent criteria. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.03.093

文献信息

• NFSI mediated C3-ether oxidation of glycals for the synthesis of hex-3-enuloses
  作者：Pradip Das、Rima Thakur

  DOI：10.1016/j.carres.2024.109032

  日期：2024.2

  constitute a vital carbohydrate synthetic intermediate that provide access to wide range of chiral molecules through diverse derivatizations. Herein we report synthesis of these fascinating scaffolds by oxidation of C3-ether protections on glycals in presence of N-fluorobenzenesulfonimide (NFSI) under Cu(I) catalysed conditions. Benzyl, methyl and silyl ethers have been efficiently oxidized to the carbonyl

  Hex-3-enulose 是一种重要的碳水化合物合成中间体，可通过不同的衍生化获得多种手性分子。在此，我们报道了在N-氟苯磺酰亚胺 (NFSI)存在下，在 Cu(I) 催化条件下，通过氧化糖醛上的 C3-醚保护来合成这些令人着迷的支架。苄基醚、甲基醚和甲硅烷基醚已被有效氧化成羰基。已发现氧化具有高度区域选择性，其中一系列保护基团能够耐受反应条件。这项工作对来自各种市售糖的吡喃糖基糖醛进行了研究，以评估广泛的底物范围。
• Vilsmeier-haack reactoin of glycals-a short route to C-2-formyl glycals
  作者：N.G. Ramesh、K.K. Balasubramanian

  DOI：10.1016/s0040-4039(00)79402-0

  日期：1991.7

  A short and straightforward route has been accomplished for the synthesis of C-2-formyl glycals by a Vilsmeier-Haack reaction of glycals.
• Aureolic acid antibiotics: synthesis of a model aglycon
  作者：Richard W. Franck、Thomas V. John

  DOI：10.1021/jo00167a022

  日期：1983.9
• GUANIDINO-SUBSTITUTED COMPOUNDS
  申请人：Allelix Biopharmaceuticals Inc.

  公开号：EP0757695A1

  公开（公告）日：1997-02-12
• [EN] GUANIDINO-SUBSTITUTED COMPOUNDS<br/>[FR] COMPOSES SUBSTITUES PAR GUANIDINO
  申请人：ALLELIX BIOPHARMACEUTICALS INC.

  公开号：WO1995029926A1

  公开（公告）日：1995-11-09

  (EN) Novel guanidino-substituted compounds are described having general formula (I) or a salt, hydrate or solvate thereof, in which X is selected from C, O, N and S; R1 and R3 are independently -(W)a-(R6)b-Z, wherein a and b are independently 0 or 1; W is NH, O or S; R6 is C1-8alkylene in which one or two non-adjacent, intervening carbon atoms thereof is optionally replaced with nitrogen or oxygen; and Z is H, OH or -NH-C(NH)-NH2; provided that when b is 0 then Z is H; R2 is selected from H and OH; and R4 and R5 are independently C1-8alkylene in which one of the carbon atoms thereof is optionally replaced with nitrogen or oxygen. Compounds in accordance with formula (I) have been found to inhibit HIV replication.(FR) Nouveaux composés substitués par guanidino correspondant à la formule générale (I), ou leur sel, hydrate ou solvate. Dans cette formule, X est choisi entre C, O, N et S; R1 et R3 représentent indépendamment -(W)a-(R6)b-Z, où a et b valent séparément 0 ou 1; W représente NH, O ou S; R6 représente alkylène C1-8 dont un ou deux atomes de carbone intermédiaires et non adjacents sont éventuellement remplacés par azote ou oxygène; et Z représente H, OH ou -NH-C(NH)-NH2, à condition que Z représente H quand b vaut 0; R2 est choisi entre H et OH; et R4 et R5 représentent indépendamment alkylène C1-8 dont un des atomes de carbone est éventuellement remplacé par azote ou oxygène. Des composés conformes à la formule (I) inhibent la réplication du VIH.