3-O-Acetyl-1,2-O-isopropyliden-α-D-xylofuranose | 59940-64-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-Acetyl-1,2-O-isopropyliden-α-D-xylofuranose
• 英文别名: [(3aR,5R,6S,6aR)-5-(hydroxymethyl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] acetate
• CAS: 59940-64-6
• 化学式: C₁₀H₁₆O₆
• 分子量: 232.233
• InChiKey: QEROQENRHNMWGZ-BZNPZCIMSA-N

物化性质

• 沸点：
  312.7±42.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-O-Acetyl-1,2-O-isopropyliden-α-D-xylofuranose 以 醋酸异丙酯 、 水 为溶剂， 反应 12.0h， 生成 5-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose
  参考文献：
  名称：

  [EN] METHOD OF PREPARING DEOXYRIBOFURANOSE COMPOUNDS
  [FR] MÉTHODE DE SYNTHÈSE DE DÉSOXYRIBOFURANNOSES

  摘要：

  本发明涉及制备脱氧核糖类化合物的方法，例如化合物（2），这些化合物是制备药物化合物（例如5-氨基-3-（2'-O-乙酰基-3'-脱氧-β-D-核糖呋喃基）-3H-噻唑并[4,5-d]嘧啶-2-酮等）中有用的中间体。

  公开号：

  WO2010057103A1
• 作为产物：
  描述：

  [(3aR,5R,6S,6aR)-6-acetyloxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl butanoate 在 Candida cylindracea lipase 、 phosphate buffer (0.1 M, ph=7) 作用下， 生成 3-O-Acetyl-1,2-O-isopropyliden-α-D-xylofuranose
  参考文献：
  名称：

  Application of lipases in the removal of protective groups on glycerides and glycosides

  摘要：

  DOI：

  10.1016/s0040-4039(00)96264-6

文献信息

• A mild and selective cleavage of trityl ethers by CBr4–MeOH
  作者：Jhillu S. Yadav、Basi V. Subba Reddy

  DOI：10.1016/s0008-6215(00)00241-x

  日期：2000.12

  Trityl ethers are selectively deprotected to the corresponding alcohols in high yields by CBr4 in refluxing methanol under neutral reaction conditions. Other hydroxyl protecting groups like isopropylidene, allyl, benzyl, acetyl, benzoyl, methyl, tosyl, prenyl, propargyl, tert-butyldiphenylsilyl and p-methoxybenzyl ethers are unaffected.

  在中性反应条件下，在回流的甲醇中，通过CBr4将三苯甲基醚高选择性地脱保护为相应的醇。其他羟基保护基如异亚丙基，烯丙基，苄基，乙酰基，苯甲酰基，甲基，甲苯磺酰基，异戊二烯基，炔丙基，叔丁基二苯基甲硅烷基和对甲氧基苄基醚不受影响。
• An extremely simple, convenient, and selective method for acetylating primary alcohols in the presence of secondary alcohols
  作者：Kazuaki Ishihara、Hideki Kurihara、Hisashi Yamamoto

  DOI：10.1021/jo00067a005

  日期：1993.7

  Reaction of primary-secondary diols with acetyl chloride in dichloromethane in the presence of 2,4,6-collidine, NN-diisopropylethylamine, or 1,2,2,6,6-pentamethylpiperidine (PMP) leads to the corresponding primary monoacetates simply, conveniently, and in good yields. In this way, other acyl chlorides, sulfonyl chlorides, and silyl chlorides in place of acetyl chloride also react with primary hydroxyl group selectively.
• Detritylation of mono- and di-saccharide derivatives using ferric chloride hydrate
  作者：Xianglan Ding、Wei Wang、Fanzuo Kong

  DOI：10.1016/s0008-6215(97)00190-0

  日期：1997.10

  Quantitative detritylation of mono-and di-saccharide derivatives of diverse structure was achieved with FeCl3.6H(2)O in CH2Cl2 at room temperature. Benzyl, isopropylidene, isopropylthio, allyl, acetyl, and benzoyl O-protecting groups were not effected under the designated conditions. (C) 1997 Elsevier Science Ltd.
• Highly Efficient Deacetylation by Use of the Neutral Organotin Catalyst [tBu2SnOH(Cl)]2
  作者：Akihiro Orita、Yuuki Hamada、Takehiko Nakano、Shinji Toyoshima、Junzo Otera

  DOI：10.1002/1521-3765(20010803)7:15<3321::aid-chem3321>3.0.co;2-h

  日期：2001.8.3

  Deprotection of acetyl esters is effected cleanly by the neutral organotin catalyst, [tBu(2)SnOH(Cl)](2). The mildness of the reaction gives rise to great synthetic versatility and in the process a variety of functional groups are tolerated. Differentiations between primary, secondary, and tertiary alcohols and between acetyl ester and other esters are feasible. No racemization occurs with chiral acetyl esters. Exclusive deprotection of primary acetyl esters in carbohydrates and nucleosides is observed. The crude product thus obtained can be used for further reactions without purification.
• KLOOSTERMAN, M.;MOSMULLER, E. W. J.;SCHOEMAKER, H. E.;MEIJER, E. M., TETRAHEDRON LETT., 28,(1987) N 26, 2989-2992
  作者：KLOOSTERMAN, M.、MOSMULLER, E. W. J.、SCHOEMAKER, H. E.、MEIJER, E. M.

  DOI：——

  日期：——