methyl-3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside | 77398-20-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl-3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside
• 英文别名: β-methyl daunosaminid；methyl β-L-daunosamine；Methyl beta-L-daunosaminide；(2S,3S,4S,6S)-4-amino-6-methoxy-2-methyloxan-3-ol
• CAS: 77398-20-0
• 化学式: C₇H₁₅NO₃
• 分子量: 161.201
• InChiKey: UIWJWFKPPXKEJV-ZTYPAOSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  64.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl-3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside 在 盐酸 作用下， 反应 2.0h， 生成 3-amino-2,3,6-trideoxy-DL-lyxo-hexopyranoside hydrochloride
  参考文献：
  名称：

  Synthesis of a new hapten for generating catalytic antibodies that activate doxorubicin prodrugs

  摘要：

  In order to assess a novel strategy for catalytic activation of a new prodrug of doxorubicin, a new hapten has been designed and prepared, which can be used to induce an immune response from which catalytic antibodies (cAbs) may be produced. (C), 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01681-1
• 作为产物：
  描述：

  ((2S,3R,4S,6S)-3-Hydroxy-6-methoxy-2-methyl-tetrahydro-pyran-4-yl)-carbamic acid methyl ester 在 吡啶 、 barium dihydroxide 、 AG-1-X₄ (OH- form) 、 sodium acetate 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 65.0h， 生成 methyl-3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside
  参考文献：
  名称：

  利用非对映选择性分子内[3 + 2]环加成法完全合成二十烷胺和柔红胺

  摘要：

  通过非对映选择性分子内的硝酮-烯烃环化反应已完成了道诺胺（3）和二十二胺（4）的全合成。在关键步骤中，手性硝酮12a环化以得到82:18比例的两个异恶唑烷13a和14a。对13a的进一步加工导致了道诺胺和二十二胺。还检查了烯烃取代对环加成的非对映选择性的影响。

  DOI：

  10.1016/s0040-4020(01)96700-6

文献信息

• A new reagent and its polymer-supported variant for the amidination of amines
  作者：Gerald Dräger、Wladimir Solodenko、Josef Messinger、Uwe Schön、Andreas Kirschning

  DOI：10.1016/s0040-4039(01)02403-0

  日期：2002.2

  New reagents for the high yielding amidination of primary and secondary amines are described. By attaching a benzyl substituent to the 3,5-dimethyl-1H-pyrazole-1-carboxamidine ring, a reagent 1 is obtained which allows easy work-up after amidination because of solubility of byproducts in organic solvents. In addition, the polystyrene-bound analogue 2 was prepared which allows amidination of various

  描述了用于伯胺和仲胺的高产率酰胺化的新试剂。通过将苄基取代基连接到3，5-二甲基-1 H-吡唑-1-羧am环上，获得试剂1，由于副产物在有机溶剂中的溶解性，该试剂1在酰胺化后易于后处理。另外，制备了聚苯乙烯结合的类似物2，其允许以高纯度酰胺化各种胺。
• 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。
• Total synthesis of acosamine and daunosamine utilizing a diastereoselective intramolecular [3+2] cycloaddition
  作者：P.M. Wovkulich、M.R. Uskoković

  DOI：10.1016/s0040-4020(01)96700-6

  日期：1985.1

  acosamine (4) has been accomplished via a diastereoselective intramolecular nitrone-olefin cyclization. In the key step the chiral nitrone 12a cyclized to give two isoxazolidines 13a and 14a in an 82:18 ratio. Further elaboration of 13a led to daunosamine and acosamine. The effects of olefin substitution on the diastereoselectivity of the cycloaddition was also examined.

  通过非对映选择性分子内的硝酮-烯烃环化反应已完成了道诺胺（3）和二十二胺（4）的全合成。在关键步骤中，手性硝酮12a环化以得到82:18比例的两个异恶唑烷13a和14a。对13a的进一步加工导致了道诺胺和二十二胺。还检查了烯烃取代对环加成的非对映选择性的影响。
• Synthesis of a new hapten for generating catalytic antibodies that activate doxorubicin prodrugs
  作者：Carlos Jiménez、Alfonso Tramontano

  DOI：10.1016/s0040-4039(01)01681-1

  日期：2001.10

  In order to assess a novel strategy for catalytic activation of a new prodrug of doxorubicin, a new hapten has been designed and prepared, which can be used to induce an immune response from which catalytic antibodies (cAbs) may be produced. (C), 2001 Elsevier Science Ltd. All rights reserved.