methyl 2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside | 91463-72-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: methyl 2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside
• 英文别名: (2S,3S,6R)-6-methoxy-2-methyl-3,6-dihydro-2H-pyran-3-ol
• CAS: 91463-72-8
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: BPAHQTJCFQUBHC-LYFYHCNISA-N

物化性质

• 沸点：
  239.3±40.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside 在 盐酸 、 N-碘代丁二酰亚胺 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium hydride 作用下， 以 甲醇 、 氯仿 、 苯 为溶剂， 反应 38.5h， 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
• 作为产物：
  描述：

  (2S,3R,6R)-3,6-Dimethoxy-2-methyl-3,6-dihydro-2H-pyran 在 sodium methylate 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 methyl 2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside
  参考文献：
  名称：

  Synthèse de disaccharides polydésoxygénés et iodés

  摘要：

  3-Amino-polydeoxy disaccharides have been prepared by condensation of a glycal with methyl 2,3,6-trideoxy-alpha-L-erythro- (or threo)-hex-2-enopyranoside in the presence of N-iodosuccinimide. After acid hydrolysis of the glycoside, 1,4-addition of hydrazoic acid to the corresponding hex-2-enopyranose led to 3-azido-disaccharides which were acetylated. Reduction of the azido group gave 2,2'-dideoxy- or 2,2'-dideoxy-2'-iodo compounds. Condensation of O-(3,4-di-O-acetyl-2,6-dideoxy-2-iodo-alpha-L-manno-hexopyranosyl)-(1 --> 4)-1-O-acetyl-2,3,6-trideoxy-3-trifluoroacetamido-alpha-L-arabino-hexopyranose with daunomycinone, followed by 3',4'-O-deacetylation produced the new anthracycline, 7-O-[O-(2,6-dideoxy-2-iodo-alpha-L-manno-hexopyranosyl)-(1 --> 4)-2,3,6-trideoxy-3-trifluoroacetamido-alpha-L-arabino-hexopyranosyl]-daunomycinone.

  DOI：

  10.1016/s0008-6215(00)90558-5

文献信息

• A new route to (±)-daunosamine and related amino-sugars
  作者：Peter G. Sammes、Dean Thetford

  DOI：10.1039/c39850000352

  日期：——

  1-(2-Furyl)ethanol has been converted into (±)-daunosamine by use of a modified Mitsunobu reaction.

  使用改良的Mitsunobu反应将1-（2-呋喃基）乙醇转化为（±）-柔红胺。
• 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。
• Synthesis of <scp>l</scp>-Daunosamine and <scp>l</scp>-Ristosamine Glycosides via Photoinduced Aziridination. Conversion to Thioglycosides for Use in Glycosylation Reactions
  作者：Matthew T. Mendlik、Peng Tao、Christopher M. Hadad、Robert S. Coleman、Todd L. Lowary

  DOI：10.1021/jo061167z

  日期：2006.10.1

  l-ristosamine glycosides is reported. Photoreaction of methyl 4-O-azidocarbonyl-2,3,6-trideoxy-l-hex-2-enopyranosides, followed by aziridine opening, leads to 3-amino-3-N-,4-O-carbonyl-2,3,6-trideoxy precursors to the aminosugar methyl glycosides. Conversion of these precursors to their thioglycoside analogues followed by N-acetylation of the carbamate moiety permits high yielding and, in some cases, stereoselective

  据报道，将光诱导的酰基氮烯叠氮化用于合成l-柔丹胺和1- ristosamine糖苷。甲基4 - O-叠氮基羰基-2,3,6-三苯氧基-1-己-2--2-吡喃侧葡糖苷的光反应，然后打开氮丙啶，导致3-氨基-3- N-，4 - O-羰基-2,3氨基糖甲基糖苷的-6-三甲氧基前体。这些前体转化为其硫代糖苷类似物，然后对氨基甲酸酯部分进行N-乙酰化，可实现高收率，在某些情况下，使用由Crich和其同事开发的1-苯亚磺酰基哌啶-三氟甲磺酸酐活化方法可实现立体选择性糖基化。糖基化涉及N的激活-碘代琥珀酰亚胺和三氟甲磺酸银也成功，但是这些反应的立体选择性通常较低。
• A short, efficient route to a protected daunosamine from L-rhamnose
  作者：Henry W. Pauls、Bert Fraser-Reid

  DOI：10.1039/c39830001031

  日期：——

  The imidate ester obtained from the reaction of methyl 2,3,6-trideoxy-α-L-threo-hex-2-enopyranoside with trichloroacetonitrile undergoes iodonium ion-induced cyclisation, and the dihydroxazole product is subjected to reductive dehalogenation to give a protected from of daunosamine.

  从甲基-2,3,6-三脱氧-α-α-的反应得到的亚胺酯大号-苏式-己-2-烯吡喃糖苷与三氯乙腈经受碘鎓离子诱导的环化，并且二氢恶唑产物进行还原性脱卤化，得到被保护来自道诺沙胺。
• 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。