6-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose | 32754-29-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose
• 英文别名: (R)-2-Hydroxy-2-((3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethyl acetate；[(2R)-2-[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl] acetate
• CAS: 32754-29-3
• 化学式: C₁₁H₁₈O₇
• 分子量: 262.26
• InChiKey: WXJUNIGVSOENPU-JDDHQFAOSA-N

物化性质

• 熔点：
  147 °C (decomp)
• 沸点：
  432.4±40.0 °C(Predicted)
• 密度：
  1.304±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 在 吡啶 、 ruthenium trichloride 、 sodium periodate 、 氯化亚砜 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.0h， 生成 6-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose 3,5-cyclic sulfate
  参考文献：
  名称：

  Cyclic sulfates in the regioselective synthesis of 5- and 6-amino and 5- and 6-fluorohexofuranoses

  摘要：

  Cyclic sulfates of 5,6- and 3,5-D-glucofuranose were used to prepare 6- and 5-azido (amino) and 6- and ti-fluoro derivatives of 1,2-O-isopropylidenehexofuranoses (D-gluco and L-ino configurations). The reactions were completely regioselective and, in the case of stereogenic centers (substitution at C-5), completely stereoselective. (C) 1999 Elsevier Science Ltd, All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00124-x
• 作为产物：
  描述：

  1,2-o-异亚丙基-alpha-d-呋喃葡萄糖-3-乙酸酯 在 ammonium hydroxide 作用下， 生成 6-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose
  参考文献：
  名称：

  Josephson, Justus Liebigs Annalen der Chemie, 1929, vol. 472, p. 217,228

  摘要：

  DOI：

文献信息

• Regioselective O-deacylation of fully acylated glycosides and 1,2-O-isopropylidenealdofuranose derivatives with hydrazine hydrate
  作者：Hoshiharu Ishido、Nobuo Sakairi、Masao Sekiya、Nobuo Nakazaki

  DOI：10.1016/s0008-6215(00)80525-x

  日期：1981.11

  partial O -deacylation of fully acylated methyl glycosides and some other glycosyl compounds (23 compounds) was found to be induced, to give, in good yields, products bearing one free hydroxyl group; the results obtained indicated that, among the primary and secondary O -acyl groups, the 2- O -acyl groups were, in general, the most labile toward the nucleophile (hydrazine). Hydrazinolysis of 1,2- O -

  摘要在1：4乙酸-吡啶中进行肼解后，在吡啶中，可诱导完全酰化的甲基糖苷和某些其他糖基化合物（23种化合物）的部分O-脱酰作用，从而以较高的收率得到含1种化合物的产物。游离羟基 所得结果表明，在伯和仲O-酰基中，2-O-酰基通常对亲核试剂（肼）最不稳定。另一方面，对1，2-O-异亚丙基戊二醛呋喃糖酰化物（3种化合物）进行水合肼解，以高收率得到相应的在其伯羟基上具有保护基的单酰基衍生物。讨论了可能与肼解的区域选择性有关的因素。
• An Improved Procedure for the Regioselective Acetylation of Monosaccharide Derivatives by Pancreatin-Catalyzed Transesterification in Organic Solvents
  作者：Fritz Theil、Hans Schick

  DOI：10.1055/s-1991-26510

  日期：——

  A series of pyranosidic and furanosidic monosaccharide derivatives were monoacetylated in the 6-position with high regioselectivity and good to excellent yields by the pancreatin-catalyzed transesterification with vinyl acetate in the solvent system tetrahydrofuran/triethylamine.

  一系列吡喃糖和呋喃糖的单糖衍生物在6位上通过胰酶催化的酯交换反应，与乙酸乙烯酯在四氢呋喃/三乙胺溶剂体系中进行，实现了高度区域选择性的单乙酰化，产率良好至优秀。
• Ceric Ammonium Nitrate/Pyridine: A Mild Reagent for the Selective Deprotection of Cyclic Acetals and Ketals in the Presence of Acid Labile Protecting Groups
  作者：Michelangelo Parrilli、Gaspare Barone、Emiliano Bedini、Alfonso Iadonisi、Emiliano Manzo

  DOI：10.1055/s-2002-34225

  日期：——

  The reagent system ceric ammonium nitrate/pyridine can perform the cleavage of primary and (in some cases) secondary acetonides, benzylidenes and tetrahydropyranyl ethers. The mild acididity of the reaction system (pH 4.4) allows deprotections to be performed in the presence of several acid labile protecting groups.

  试剂系统硝酸铈铵/吡啶可以进行一级和（在某些情况下）二级丙酮化物、亚苄基和四氢吡喃基醚的裂解。反应系统的温和酸性 (pH 4.4) 允许在几个酸不稳定保护基团的存在下进行脱保护。
• Application of Ortho Esterification under Kinetically Controlled Conditions to the Selective Acylation in the D-Gluco-, D-Ribo- and D-Xylo-furanose Series
  作者：Mohamed Bouchra、Pierre Calinaud、Jacques Gelas

  DOI：10.1055/s-1995-3955

  日期：1995.5

  The ortho esterification of various glucofuranoses in the D-ribo-, D-xylo and D-gluco series under kinetic control was obtained through the action of 1,1-dimethoxyethene (a ketene acetal) on the monosaccharide using mild acid conditions. The selective hydrolysis of the methoxyethylidene derivatives thus obtained, gave access to α-hydroxy acetates which are useful synthetic intermediates.

  D-核糖、D-木糖和 D-葡萄糖系列中的各种呋喃葡萄糖在动力学控制下的原酯化是通过 1,1-二甲氧基乙烯（乙烯酮缩醛）在弱酸条件下与单糖的作用来实现的。由此获得的甲氧基亚乙基衍生物的选择性水解，得到α-羟基乙酸酯，这是有用的合成中间体。
• Selective transformation of acetonides to orthoesters: an application of a photoinduced electron transfer process
  作者：Mariella Mella、Maurizio Fagnoni、Angelo Albini

  DOI：10.1016/s0040-4020(00)01011-5

  日期：2001.1

  Irradiation of alpha,beta -acetonides of polyols and sugars in the presence of benzene 1,2,4,5-tetracarbonitrile causes cleavage of a methyl radical and generates an alpha,alpha -dioxy carbocation. The subsequent nucleophile addition gives different kinds of derivatives depending on the acetonide structure. Cyclic othoesters are formed when a delta -hydroxyl group is present, while in the other case, intermolecular trapping by moisture, present in the solvent (acetonitrile) or by added alchols occurs and gives orthoacids. With galactopyranose acetonide, efficient intermolecular trapping by a second molecule of sugar has been obtained. Useful synthetic intermediates such as hydroxy acetates are in turn obtained by selective hydrolysis of the methoxyethylidene derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.