Methyl 4-O-acetyl-3-acetamido-2,3,6-trideoxy-α-L-lyxopyranoside | 18981-63-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 4-O-acetyl-3-acetamido-2,3,6-trideoxy-α-L-lyxopyranoside
• 英文别名: methyl di-N,O-acetyl-α-L-daunosaminide；Methyl-N,O-diacetyl-α-daunosaminid；methyl N,O-diacetyl-α-L-daunosaminide；N,O-diacetyl-α-daunosaminide；α-Methyl-L-daunosaminid-N,O-diacetat；[(2S,3S,4S,6R)-4-acetamido-6-methoxy-2-methyloxan-3-yl] acetate
• CAS: 18981-63-0
• 化学式: C₁₁H₁₉NO₅
• 分子量: 245.276
• InChiKey: SBJRRLJCQHFWCN-BOWGKDCGSA-N

物化性质

• 沸点：
  394.4±42.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 3-amino-2,3,6-trideoxy-N,O-(2,2,2-trichloroethylethylidene)-α-L-lyxo-hexopyranoside 生成 Methyl 4-O-acetyl-3-acetamido-2,3,6-trideoxy-α-L-lyxopyranoside
  参考文献：
  名称：

  SAMMES, PETER G.;THETFORD, DEAN, J. CHEM. SOC. PERKIN TRANS., 1,(1988) N 1, 111-123

  摘要：

  DOI：

文献信息

• Stereocontrolled routes to cis-hydroxyamino sugars, part VII: synthesis of daunosamine and ristosamine
  作者：Henry W. Pauls、Bert Fraser-Reid

  DOI：10.1016/0008-6215(86)80009-x

  日期：1986.8

  The nitrogen of an allylic amine can serve as the fulcrum for stereocontrolled delivery of oxygen to an adjacent trigonal site, and cis-hydroxyamino sugars can thus be prepared. Methods for achieving the complementary procedure, namely, control of the delivery of nitrogen to an adjacent site by an allylic oxygen, are described. For example, treatment of methyl 2,3,6-trideoxy-alpha-L-erythro-hex-2-enopyranoside

  烯丙基胺的氮可以用作支点，用于将氧立体控制地递送至相邻的三角位点，因此可以制备顺式-羟基氨基糖。描述了用于实现互补过程的方法，即，通过烯丙基氧控制氮向相邻部位的递送的控制。例如，用三氯乙腈处理甲基2,3,6-三甲氧基-α-L-赤-己基-2-烯吡喃糖苷得到亚氨酸酯，该亚氨酸酯与高氯酸二可合碘鎓反应，得到2-三氯甲基-（甲基2,3,4 ，6-四脱氧-2-碘-α-L-altropyranosido）-[3,4-d] -2-恶唑系。该产物的彻底还原性脱卤，然后水解，得到甲基N-乙酰基-α-L-豆蔻酰胺。使用一系列类似的反应来制备相应的柔红酰胺。
• Antibiotikamodelle, 3. Asymmetrisch induzierte Synthese von Aminozuckern: Derivate des Daunosamins (3‐Amino‐2,3,6‐tridesoxy‐ <scp>L</scp> ‐ <i>lyxo</i> ‐hexose)
  作者：Ingolf Dyong、Reinhard Wiemann

  DOI：10.1002/cber.19801130810

  日期：1980.8

  Das kürzlich beschriebene trans-3-3-D-glycero-4-4-((2R, 3R)-weinsäure-dimethylester)acetal (3)2) führt durch cis-Hydroxylierung mit N-Bromacetamid und Silberacetat in Eisessig hoch stereoselektiv zum 4,5-Dihydroxy-3-tosylaminoL-lyxo-hexanal-acetal 6. Dieser Daunosamin-Precursor wird in wenigen Schritten zum Methyl-4-O-acetyl-3-acetylamino-2,3,6-tridesoxy-2,3,6-6-tridesoxy-α-L-lyxo-hexosid (Methyl-N

  达斯kürzlichbeschriebene反式-3-3-D-甘油基-4-4 - （（2- [R，3 - [R）-weinsäure-二甲酯）缩醛（3）2） führt第三人以顺-Hydroxylierung MIT Ñ -Bromacetamid UND Silberacetat在Eisessig HOCH立体selum 4,5-二羟基-3- tosylaminoL- lyxo -hexanal-缩醛6。Dieser Daunosamin-前体在wenigen Schritten zum中的甲基4- O-乙酰基-3-乙酰氨基-2,3,6-三甲氧基-2,3,6-6-三甲氧基-α-L- lyxo - hexosidid（甲基-N，O-二乙酰基-α-柔红霉素）（12）。
• Mondelli, Rosanna; Arnone, Alberto; Fronza, Giovanni, Journal of Chemical Research, Miniprint, 1984, # 6, p. 1717 - 1737
  作者：Mondelli, Rosanna、Arnone, Alberto、Fronza, Giovanni、Cassinelli, Giuseppe、Gioia, Bruno、Vigevani, Aristide

  DOI：——

  日期：——
• Regio- and stereoselective synthesis of methyl .alpha.-L-daunosaminide hydrochloride
  作者：Giuliana Cardillo、Mario Orena、Sergio Sandri、Claudia Tomasini

  DOI：10.1021/jo00195a013

  日期：1984.10
• Synthesis of <scp>l</scp>-Daunosamine Derivatives on the Basis of the Asymmetric Dihydroxylation of 3-((<i>E</i>)-1-Propenyl)-4,5-dihydroisoxazole
  作者：Peter A. Wade、Stephen G. D'Ambrosio、Jetla Appa Rao、Sharmila Shah-Patel、Damien T. Cole、James K. Murray,、Patrick J. Carroll

  DOI：10.1021/jo962293d

  日期：1997.5.1

  Methyl L-N,O-diacetyldaunosaminide was prepared from 3-nitro-4,5-dihydroisoxazole in 8.5% overall yield. A key step in the synthesis involved the AD reaction of (E)-3-(1-propenyl)-4,5-dihydroisoxazole (2b), affording the corresponding diol in 76% yield (92% ee). A second key step involved reductive cleavage of the dihydroisoxazole 4a and subsequent N-acetylation to afford separable diastereomeric gamma-(acetylamino)alcohols 7a and 8a in 62% yield (72:28, 7a/8a). Swern oxidation of 7a and subsequent methanolysis followed by acetylation provided methyl L-N,O-diacetyldaunosaminide as an anomeric mixture. The AD reactions of chiral alkenyl dihydroisoxazole 16 with (DHQ)(2)-PHAL and (DHQD)(2)-PHAL afforded diastereomeric diol products, isolated as the acetates 18 and 19 (98:2 and 5:95 ratios, respectively, depending on the chiral auxiliary).