methyl N-acetyl-β-L-daunosamide | 57918-56-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl N-acetyl-β-L-daunosamide
• 英文别名: methyl 3-acetamido-2,3,6-trideoxy-β-L-lyxo-hexopyranoside；methyl 3-acetamido-2,3,6-trideoxy-beta-L-lyxohexopyranoside；N-[(2S,3S,4S,6S)-3-hydroxy-6-methoxy-2-methyloxan-4-yl]acetamide
• CAS: 57918-56-6
• 化学式: C₉H₁₇NO₄
• 分子量: 203.238
• InChiKey: JIZHXACDJCSYMG-IZJRFANQSA-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：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  67.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl N-acetyl-β-L-daunosamide 在 palladium on activated charcoal 、 Grubbs catalyst first generation 氢气 、 三乙胺 、 silver(l) oxide 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 、 苯 为溶剂， 反应 25.0h， 生成 1,4-bis (methyl 3'-acetamido-2',3',6'-trideoxy-β-L-lyxo-hexopyranos-4'-yi)-1,4-butanediol
  参考文献：
  名称：

  Synthesis of extended spacer-linked neooligodeoxysaccharides by metathesis olefination and evaluation of their RNA-binding properties

  摘要：

  The preparation of linear 1,4-butanediol-linked oligodeoxysugars 50-53, 58 and 60 is described which are potential binders to polynucleotides. Various aminodeoxymonosaccharides 9, 13-18, 30, 31 and 40-42 which are either allylated at the anomeric center or at C4 were subjected to the metathesis olefination protocol. Depending on the position of allylation E/Z-mixtures of C-2-symmetric head-to-head or tail-to-tail homodimers were formed. Among them, saccharides 13, 30, 31 and 40 were transformed into the corresponding 1,4-butanediol linked disaccharides 50-53 by catalytic hydrogenation of the central olefinic double bond and exhaustive deprotection. In order to target extended spacer-linked neooligosaccharides homodimeric aminoglycoside 37 was bisallylated and subjected to cross metathesis conditions using methyl 4-O-allyl daunosamide 40 as reaction partner which yielded two desired trimeric and tetrameric linearly spacer-linked daunosamine derivatives. After hydrogenation and deprotection two additional probes 58 and 60 for nucleic acid binding studies were at hand. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.013
• 作为产物：
  描述：

  methyl α-L-daunosaminide 在 水 、 三乙胺 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 0.83h， 生成 methyl N-acetyl-β-L-daunosamide
  参考文献：
  名称：

  合成己糖的新方法：进入 (.+-.)-岩藻糖和 (.+-.)-daunosamine

  摘要：

  Synthese a partir d'une cycloaddition entre l'acetaldehyde et le benzoyloxy-1 t-butyldimethylsiloxy-2 methoxy-4 butadiene-1,3

  DOI：

  10.1021/ja00291a028

文献信息

• Anthracycline glycosides
  申请人：Hoffmann-La Roche Inc.

  公开号：US04526960A1

  公开（公告）日：1985-07-02

  This invention relates to compounds of the formula ##STR1## wherein R is a hydrogen atom, a lower alkyl, aryl or aryl-(lower alkyl) group, a 5-membered or 6-membered heteroaromatic group in which the hetero atom is nitrogen, oxygen or sulphur or a group of the formula ##STR2## wherein R' is a hydroxy, lower alkoxy, amino, lower alkylamino, di-(lower alkyl)amino or arylamino group, n stands for an integer of 1 to 4, n' stands for an integer of 2 to 10, R.sup.1 and R.sup.2 each are a hydrogen atom or one of R.sup.1 and R.sup.2 is a hydrogen atom and the other is a hydroxy, lower alkoxy or benzyloxy group and X is a group of the formula ##STR3## and pharmaceutically acceptable acid addition salts thereof, a process for their manufacture and medicaments containing them. These compounds and salts possess antitumor activity.

  这项发明涉及以下公式的化合物：其中R是氢原子，较低烷基，芳基或芳基-(较低烷基)基，5-或6-成员杂芳基，其中杂原子是氮、氧或硫，或者是公式的基团：其中R'是羟基，较低烷氧基，氨基，较低烷基氨基，二-(较低烷基)氨基或芳基氨基，n代表1到4的整数，n'代表2到10的整数，R1和R2各自是氢原子，或者R1和R2中的一个是氢原子，另一个是羟基、较低烷氧基或苄氧基基团，X是以下公式的基团：及其药学上可接受的酸盐，以及包含它们的制备方法和含有它们的药物。这些化合物和盐具有抗肿瘤活性。
• Syntheses of spacer-linked neodisaccharides derived from l-daunosamine
  作者：Andreas Kirschning、Guang-wu Chen

  DOI：10.1016/s0040-4039(99)00862-x

  日期：1999.6

  The preparation of novel head-to-head spacer-linked bisdaunosamine homodimers 8, 15 and 18 is described. The synthesis is achieved by double glycosylation of monosilylated 1,4-butanediol 9 using silyl glycoside 5 as glycosyl donor. Alternatively, olefin metathesis of allyl glycosides α-11 and particularly of α-12 constitutes a second route toward 8 and its unsaturated derivative 15 while non symmetrical

  新颖头对磁头隔离联bisdaunosamine同二聚体的制备8，15和18进行说明。通过使用甲硅烷基糖苷5作为糖基供体的单甲硅烷基化的1，4-丁二醇9的双糖基化来实现合成。备选地，烯丙基糖苷α- 11，特别是α- 12的烯烃复分解构成了朝向8及其不饱和衍生物15的第二条途径，而烯丙基糖苷11和12的交叉复分解获得了不对称的二聚体18。
• A preparative synthesis of 3-amino-2,3,6-trideoxy-l-lyxo-hexose (daunosamine) hydrochloride from d-mannose
  作者：Derek Horton、Wolfgang Weckerle

  DOI：10.1016/s0008-6215(00)84166-x

  日期：1975.11

  4-O-benzoyl-6-bromide 7. Dehydrohalogenation of gives the 5,6-unsaturated glycoside 8, which, after O-debenzoylation to 9, undergoes stereospecific reduction by hydrogen with net C-5 inversion to give the crystalline, N-acetylated methyl beta-glycoside (10) of daunosamine, readily converted into daunosamine hydrochloride (11) and into the crystalline N-benzoyl (14) and N-acetyl(15) derivatives. No chromatographic

  描述了一种简单的，从甲基α-D-甘露吡喃糖苷（1）开始的九步制备方法，该方法以40％的总收率提供了标题氨基糖11，即抗肿瘤抗生素阿霉素和柔红霉素的糖成分。1的2,3：4,5-二亚苄基乙缩醛（2）被丁基锂转化为2-脱氧-3-酮3，其肟4以对D-核糖胺高的立体选择性还原为N -乙酰基衍生物5并通过N-溴琥珀酰亚胺的作用转化为4-O-苯甲酰基-6-溴化物7。的脱卤化氢得到5,6-不饱和糖苷8，在O-脱苯甲酰化为9后，通过氢与C-5净转化，得到柔红霉素的结晶N-乙酰化甲基β-糖苷（10），易转化为盐酸柔红胺（11）和结晶的N-苯甲酰基（14）和N-乙酰基（15）衍生物。在任何步骤中都不需要分离的色谱程序。
• US4024333A
  申请人：——

  公开号：US4024333A

  公开（公告）日：1977-05-17
• US4526960A
  申请人：——

  公开号：US4526960A

  公开（公告）日：1985-07-02