methyl 2,3-O-carbonyl-α-L-rhamnopyranoside | 75100-10-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-O-carbonyl-α-L-rhamnopyranoside
• 英文别名: Methyl α-L-rhamnopyranoside 2,3-carbonate；(3aR,4R,6S,7S,7aR)-7-hydroxy-4-methoxy-6-methyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2-one
• CAS: 75100-10-6
• 化学式: C₈H₁₂O₆
• 分子量: 204.18
• InChiKey: OHYAGKHFDNIJTI-PAMBMQIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  methyl 2,3-O-carbonyl-α-L-rhamnopyranoside 在 四氧化钌 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 4.0h， 生成 methyl 5-deoxy-2,3-O-carbonyl-β-D-ribofuranoside
  参考文献：
  名称：

  Collins, Peter M.; Travis, Anthony S., Journal of the Chemical Society. Perkin transactions I, 1980, p. 779 - 786

  摘要：

  DOI：
• 作为产物：
  描述：

  bis(ethoxycarbonyl) disulphide 、 甲基-Alpha-D-吡喃鼠李糖苷 在 三乙胺 作用下， 以 二甲基亚砜 、 丙酮 为溶剂， 反应 2.0h， 以30%的产率得到methyl 2,3-O-carbonyl-α-L-rhamnopyranoside
  参考文献：
  名称：

  Collins, Peter M.; Travis, Anthony S., Journal of the Chemical Society. Perkin transactions I, 1980, p. 779 - 786

  摘要：

  DOI：

文献信息

• Enantiodivergent Total Syntheses of Nanaomycins and Their Enantiomers, Kalafungins
  作者：Kuniaki Tatsuta、Kohji Akimoto、Masahiko Annaka、Yutaka Ohno、Mitsuhiro Kinoshita

  DOI：10.1246/bcsj.58.1699

  日期：1985.6

  The first, enantiospecific total syntheses of pyranonaphthoquinone antibiotics, nanaomycins D and A, and their enantiomers, kalafungin and 4-deoxykalafunginic acid are described by an “enantiodivergent” strategy from a common optically active intermediate, (1S,3RS,4S)-3,4-dihydro-5,9,10-trimethoxy-1-methyl-1H-naphtho[2,3-c]pyran-3,4-diol, which has been derived from L-rhamnose via condensation of

  第一个，吡喃萘醌抗生素，nanaomycins D 和 A 及其对映异构体，kalafungin 和 4-deoxykalafunginic 酸的对映特异性全合成是通过来自常见光学活性中间体 (1S,3RS,4S)-3 的“对映发散”策略描述的， 4-dihydro-5,9,10-trimethoxy-1-methyl-1H-naphtho[2,3-c]pyran-3,4-diol，由L-鼠李糖通过4-甲氧基-3缩合得到(苯基磺酰基)-1(3H)-异苯并呋喃酮和甲基 3,4,6-三脱氧-α-L-甘油-己基-3-烯吡喃糖苷-2-酮糖。
• Organofluorine compounds and fluorinating agents Part 17: Sonochemical-forced preparation of perfluoroalkanals and their use for non-conventional acetalations of carbohydrates
  作者：Alexey O. Miller、Dietmar Peters、Cornelia Zur、Michael Frank、Ralf Miethchen

  DOI：10.1016/s0022-1139(96)03551-8

  日期：1997.4

  The homologous 1-iodo-perfluoroalkanes 1a-1c and alpha,omega-dibromo-perfluoroalkanes 4a, 4b were carbonylated with DMF in the presence of Al/SnCl2 or Al/PbBr2 under sonication in a short reaction time. The hydrated aldehydes 2a-2c and 5a, 5b respectively were obtained in good yields allowing dehydration to 3a-3c and 6a, 6b. Some of the fluorinated aldehydes were selected as substrates in a Wittig-Homer olefination assisted by ultrasound and in non-conventional acetalations of methyl alpha-L-rhamnopyranoside (9). Thus, (E)-1-perfluorooctyl-2-phenylsulphonyl-ethene (8) was prepared from 3c and the phosphonate 7 by Wittig-Horner synthesis. Acetalations of 9 were carried out with the aldehydes (3a, 3b, 6a), hydrated aldehydes (2a, 2b), and the aldehyde hemiacetal 12 respectively, in the presence of dicyclohexylcarbodiimide (DCC). In all cases, a selective epimerization was observed at the C-atom 3 of the monosaccharide, i.e. polyfluoroalkylidenated 6-deoxy-alpha-L-altropyranosides 10, 11, 13, and 14 were obtained. (C) 1997 Elsevier Science S.A. All rights reserved.