methyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hexopyranoside | 16848-76-3

• 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: methyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hexopyranoside
• 英文别名: (4aR,6S,8aS)-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 16848-76-3
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: LASCUIFSNMHEDR-WJLOJVBCSA-N

物化性质

• 熔点：
  86-87 °C
• 沸点：
  364.1±42.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2932999099

反应信息

• 作为产物：
  描述：

  methyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 methyl 4,6-O-benzylidene-2,3-dideoxy-α-D-erythro-hexopyranoside
  参考文献：
  名称：

  Menicagli, Rita; Malanga, Corrado; Pecunioso, Angelo, Gazzetta Chimica Italiana, 1985, vol. 115, # 1, p. 23 - 28

  摘要：

  DOI：

文献信息

• Process for deoxygenating secondary alcohols
  申请人：Schering Corporation

  公开号：US04078139A1

  公开（公告）日：1978-03-07

  The process for removing a secondary hydroxyl group from an organic compound having at least one secondary hydroxyl group and having any amino groups protected, comprises the reaction of a reactive ester of said secondary hydroxyl group selected from the group consisting of an O-alkylthioester and an O-alkylselenoester with at least one mole of an organotin hydride, preferably tri-n-butylstannane, in an inert, aprotic solvent at a temperature of at least about 100.degree. C and under an inert atmosphere. The process is particularly useful in removing secondary alcohols in aminoglycoside antibiotics to produce deoxy derivatives thereof having antibacterial activity. Also described are novel O-sec.-alkylthiobenzoate, O-sec.-alkyl-S-methylxanthate, N-(sec.-alkoxythiocarbonyl)-imidazole esters, and di-O-alkylthiocarbonates having at least one secondary O-alkyl group, useful intermediates of the claimed process.

  将至少具有一个次级羟基且具有任何氨基保护的有机化合物中的次级羟基团从中去除的过程，包括将所述次级羟基团的反应性酯（所选自O-烷基硫酯和O-烷基硒酯组成的群）与至少一摩尔的有机锡氢化物（优选为三正丁基锡烷）在惰性、无极性溶剂中，在至少约100摄氏度的温度下，在惰性气氛下反应。该过程特别适用于去除氨基糖苷类抗生素中的次级醇，以产生具有抗菌活性的去氧衍生物。还描述了新颖的O-sec.-烷基硫代苯甲酸酯、O-sec.-烷基-S-甲基黄原酸酯、N-(sec.-烷氧硫代羰基)-咪唑酯和至少具有一个次级O-烷基基团的双O-烷基硫代碳酸酯，这些是所述过程的有用中间体。
• Site-Selective Catalysis of Phenyl Thionoformate Transfer as a Tool for Regioselective Deoxygenation of Polyols
  作者：María Sánchez-Roselló、Angela L. A. Puchlopek、Adam J. Morgan、Scott J. Miller

  DOI：10.1021/jo702334z

  日期：2008.3.1

  [Graphics]We report the application of peptide-embedded imidazoles as catalysts for the site-selective delivery of the phenyl thionoformate unit as a prelude to deoxygenation reactions of polyols. Methodology was developed that allows for the synthesis of thiocarboryl derivatives based on a combination of additives that include N-alkylimidazoles and FeCl3 as co-catalysts. The use of this reagent combination leads to increased reaction rates and efficient yields relative to those of simple base-mediated reactions. In terms of controlling regioselectivity during the course of polyol modification, we found that histidine-containing peptides, in combination with FeCl3, could lead to modulation of the product distribution. Through screening of peptides and control of reaction conditions, products could be observed that reflected both the inherent preference of substrates and also reversal of inherent selectivity.
• Wickremeshinghe, L. Kirthi G.; Slessor, Keith N., Canadian Journal of Chemistry, 1980, vol. 58, p. 2628 - 2632
  作者：Wickremeshinghe, L. Kirthi G.、Slessor, Keith N.

  DOI：——

  日期：——
• MENICAGLI, R.;MALANGA, C.;PECUNIOSO, A.;LARDICCI, L., GAZZ. CHIM. ITAL., 1985, 115, N 1, 23-27
  作者：MENICAGLI, R.、MALANGA, C.、PECUNIOSO, A.、LARDICCI, L.

  DOI：——

  日期：——
• US4078139A
  申请人：——

  公开号：US4078139A

  公开（公告）日：1978-03-07