六碳氨糖盐酸盐 | 32385-06-1

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 六碳氨糖盐酸盐
• 中文别名: 甲基-L-六碳氨糖盐酸盐；氨糖衍生物1
• 英文名称: Methyl α-L-daunosaminide hydrochloride
• 英文别名: Methyl L-daunosamine hydrochloride；(2S,3S,4S,6R)-4-amino-6-methoxy-2-methyloxan-3-ol;hydrochloride
• CAS: 32385-06-1
• 化学式: C₇H₁₅NO₃*ClH
• 分子量: 197.662
• InChiKey: JVYGBUAXDCLPMP-AOAPYHFMSA-N

物化性质

• 熔点：
  175-178°C dec.
• 溶解度：
  甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.12
• 重原子数：
  12
• 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：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  六碳氨糖盐酸盐 以81的产率得到methyl 2,3,6-trideoxy-3-trifluoroacetamido-α-L-arabino-hexopyranoside
  参考文献：
  名称：

  J. Med. Chem. 1975, 18, 703-707

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl-2,3,6-tridesoxy-α-L-erythro-hex-2-enopyranoside 在 盐酸 、 4-二甲氨基吡啶 、 N-碘代丁二酰亚胺 、 偶氮二异丁腈 、 Amberlyst A 26 (OH^-) 、 三正丁基氢锡 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 苯 为溶剂， 反应 57.0h， 生成 六碳氨糖盐酸盐
  参考文献：
  名称：

  Regio- and stereoselective synthesis of methyl .alpha.-L-daunosaminide hydrochloride

  摘要：

  DOI：

  10.1021/jo00195a013

文献信息

• Total synthesis of methyl l-daunosaminide hydrochloride via chiral 1,3-oxazine
  作者：Tian Jin、Jin-Seok Kim、Yu Mu、Seok-Hwi Park、Xiangdan Jin、Jong-Cheol Kang、Chang-Young Oh、Won-Hun Ham

  DOI：10.1016/j.tet.2014.02.033

  日期：2014.4

  Total synthesis of methyl l-daunosaminide hydrochloride was achieved from readily available l-tyrosine. Key steps in this strategy were palladium(0) catalyzed stereoselective intramolecular oxazine formation and catalytic hydrogenation of oxazine intermediate. This paper reported 1H and 13C NMR data of α- and β-anomer of methyl l-daunosaminide hydrochloride.

  从容易获得的1-酪氨酸实现了甲基1-柔香胺素盐酸盐的全合成。该策略的关键步骤是钯（0）催化的立体选择性分子内恶嗪的形成和恶嗪中间体的催化加氢。本文报道了甲基1-柔红酰胺盐酸盐的α-和β-端基异构体的1 H和13 C NMR数据。
• Syntheses of derivatives of L-daunosamine and its C-3 epimer employing as the key step the asymmetric conjugate addition of a homochiral lithium amide to tert-butyl (E,E )-hexa-2,4-dienoate
  作者：Stephen G. Davies、G. Darren Smyth、Ann M. Chippindale

  DOI：10.1039/a907017f

  日期：——

  The highly diastereoselective asymmetric conjugate addition of lithium (R)-N-benzyl-α-methylbenzylamide to methyl or tert-butyl (E,E)-hexa-2,4-dienoate, followed by osmium tetroxide-catalysed dihydroxylation of the resulting adducts, provides a concise route to methyl L-daunosaminide hydrochloride and methyl 3-epi-D-daunosaminide hydrochloride, a strategy which is applicable to the synthesis of either

  锂（R）-N-苄基-α-甲基苄基酰胺的高度非对映选择性不对称共轭加成至（E，E）-己二酸-6,2-二烯酸叔丁酯或叔丁基，然后四氧化os催化所得加合物的二羟基化，提供了获得甲基L-柔红酰胺盐酸盐和甲基3- epi - D的简洁途径-达柔诺胺盐酸盐，该策略适用于这些化合物的任一对映异构体的合成。关键的二羟基化反应的选择性可以通过采用Sharpless不对称二羟基化方案来显着提高。由于低选择性或需要过多的步骤，使用碘代内酯化或碘代环氨基甲酸酯化反应作为关键步骤的可能替代策略被发现不太令人满意。
• The design, synthesis, and evaluation of two universal doxorubicin-linkers: Preparation of conjugates that retain topoisomerase II activity
  作者：Chengzao Sun、Simon E. Aspland、Carlo Ballatore、Rosario Castillo、Amos B. Smith、Angelo J. Castellino

  DOI：10.1016/j.bmcl.2005.09.046

  日期：2006.1

  The design, synthesis, and evaluation of two N-alkylmaleimide aldehydes have been achieved, which upon reductive alkylation with the C3'-amino group of doxorubicin (DOX) permits the preparation of DOX conjugates via Michael addition of thiol-containing vectors. This method enables the mild, facile, and high-throughput preparation of DOX conjugates that retain the basic C3'-nitrogen, a pre-requisite for topoisomerase II inhibition. Seven DOX-amino acid conjugates were prepared, each displaying similar inhibitory activity as the parent drug. (c) 2005 Elsevier Ltd. All rights reserved.
• A New Route to 3-Amino Sugars. A Concise Synthesis of <scp>l</scp>-Daunosamine and <scp>d</scp>-Ristosamine Derivatives
  作者：Mukund P. Sibi、Jianliang Lu、Jessica Edwards

  DOI：10.1021/jo970576f

  日期：1997.8.1

  An asymmetric aldol strategy has been developed for the synthesis of L-daunosamine and D-ristosamine derivatives starting from noncarbohydrate precursors. Lithium and boron enolate mediated aldol reactions of 12 with O-TBS lactaldehyde gave non-Evans syn and Evans syn aldol products, respectively, with high selectivity. The chemical efficiency of the lithium enolate reactions were higher than the corresponding reactions with the boron enolates. Curtius rearrangement of lactone acids 23 and 26 gave the corresponding N-BOC amino lactones 30 and 32 in 64% and 62%, respectively, with complete retention of configuration. Lactone 30 was converted by a two-step sequence to N-benzoyldaunosamide 40. The overall yield for the amino sugar 40 was 18% over six steps. Similarly, lactone 32 was converted to N-benzoylristosamide 42 with an overall yield of 18% starting from 12.
• Sammes, Peter G.; Thetford, Dean, Journal of the Chemical Society. Perkin transactions I, 1988, p. 111 - 124
  作者：Sammes, Peter G.、Thetford, Dean

  DOI：——

  日期：——