methyl 3,4,6-tri-O-acetyl-2-bromo-2-deoxy-β-D-arabino-hexopyranoside | 2873-28-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4,6-tri-O-acetyl-2-bromo-2-deoxy-β-D-arabino-hexopyranoside
• 英文别名: methyl 3,4,6-tri-O-acetyl-2-bromo-2-deoxy-β-D-glucopyranoside；3,4,6-Tri-O-acetyl-2-brom-2-desoxy-methyl-β-D-glucopyranosid；D-Glucal-3,4,6-triacetat-bromid-methoxid；2-Brom-3,4,6-tri-O-acetyl-2-desoxy-methyl-β-D-glucopyranosid；methyl-(tri-O-acetyl-2-bromo-2-deoxy-β-D-glucopyranoside)；Methyl-(tri-O-acetyl-2-brom-2-desoxy-β-D-glucopyranosid)；Methyl-(2-brom-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosid)；2-Brom-3,4,6-triacetyl-2-desoxy-methyl-β-D-glucopyranosid；[(2R,3R,4S,5R,6R)-3,4-diacetyloxy-5-bromo-6-methoxyoxan-2-yl]methyl acetate
• CAS: 2873-28-1
• 化学式: C₁₃H₁₉BrO₈
• 分子量: 383.193
• InChiKey: FQZHEAHOMRPVCY-SYLRKERUSA-N

物化性质

• 熔点：
  138-139 °C
• 沸点：
  417.5±45.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  97.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3,4,6-tri-O-acetyl-2-bromo-2-deoxy-β-D-arabino-hexopyranoside 在 ammonium hydroxide 作用下， 生成 甲基3-氨基-3-脱氧-beta-D-阿卓吡喃糖苷
  参考文献：
  名称：

  Levene; Meyer, Journal of Biological Chemistry, 1923, vol. 55, p. 221,224

  摘要：

  DOI：
• 作为产物：
  描述：

  2-hydroxy-L-rhamnal acetate 在 四氯化碳 、 溴 作用下， 生成 methyl 3,4,6-tri-O-acetyl-2-bromo-2-deoxy-β-D-arabino-hexopyranoside 、 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Fischer,E.; Bergmann; Schotte, Chemische Berichte, 1920, vol. 53, p. 520

  摘要：

  DOI：

文献信息

• Substituent Dependence of the Diastereofacial Selectivity in Iodination and Bromination of Glycals and Related Cyclic Enol Ethers
  作者：Antonella Boschi、Cinzia Chiappe、Antonietta De Rubertis、Marie Françoise Ruasse

  DOI：10.1021/jo000799x

  日期：2000.12.1

  azide trapping of any cationic intermediate, it is concluded that these brominations which do not go through an ionic intermediate are concerted additions of bromine and methanol with very loose rate- and product-determining transition states. Finally, the substituent conformation at C-4 influences drastically the stereoselectivity in all these brominations. Evidence for alpha-anomeric control of the

  已经比较了在各种条件下三-O-苄基-D-葡萄糖的亲电子碘化和溴化的立体化学过程与取代的二氢吡喃2-5的立体化学过程。在乙腈中存在或不存在苄氧基取代基的情况下，在乙腈中添加IN（3）可以得到反式α-碘叠氮化物（80-87％），除了少量反式β-加合物外与桥接的碘鎓离子中间体达成协议。相反，通过开放的溴氧碳鎓离子在二氯乙烷中添加溴的非对映选择性在很大程度上取决于取代基。在没有C-4和C-5取代基的情况下，反式-二溴化物是主要的（85-95％）加合物，而在它们的存在下，对顺式-α-加成具有中等至排他选择性（60-99％）被观察到。当在相同溶剂中但用三溴化物离子盐进行溴化反应时，无论取代基是什么，都再次观察到反式α加成的优势，支持在这些条件下两个溴原子的一致加成。最后，在甲醇中添加溴表现出完全不同的行为，即非选择性形成反式α-和反-β-甲氧基溴化物，并且对取代基的依赖性很小。与不存在任何阳离子中间体
• A New Catalytic Route for the Oxidative Halogenation of Cyclic Enol Ethers using Tungstate Exchanged on Takovite
  作者：B. Sels、P. Levecque、R. Brosius、D. De?Vos、P. Jacobs、D.?W. Gammon、H.?H. Kinfe

  DOI：10.1002/adsc.200404138

  日期：2005.1

  An efficient and benign method for the regio- and stereoselective synthesis of halohydrins and β-halo ethers from dihydropyrans, dihydrofurans and anhydro sugars in the presence of a halide salt and hydrogen peroxide is presented with tungstate-exchanged takovite as oxidation catalyst.

  提出了一种高效，良性的方法，该方法用于在卤化物盐和过氧化氢的存在下，由钨酸盐交换的塔科维特作为氧化催化剂，从二氢吡喃，二氢呋喃和无水糖区域和立体选择性地合成卤代醇和β-卤代醚。
• Synthesis of 6-Hydroxy-L-Daunosamine and L-Daunosamine Derivatives
  作者：Laurent Daley、Pierre Roger、Claude Monneret

  DOI：10.1080/07328309708006508

  日期：1997.1.1

  Methyl 3-trifluoroacetamido-2,3-dideoxy-alpha-L-lyxo-hexopyranoside (19) has been synthesized from D-glucose derivatives following two pathways. The first one involving 1,2:5,6-di-O-isopropylidene-alpha-D-glucopyranose as starting material is mainly based upon azidation at C-3, inversion of configuration at C-5 and then radical deoxygenation at C-2 (13 steps and 10% overall yield). This pathway also afforded methyl N-trifluoroacetyl-alpha-L-daunosamine 22. The second pathway, which started from tri-O-acetyl-D-glucal, relied essentially upon Michael addition of N3H on the corresponding hex-2-enose and glycosidation of the two pivaloyl compounds 33 and 34. After the beta-D-ribo isomer 34 was subsequently converted into its beta-methyl glycoside 28b, inversion of configuration at C-5 was carried out via the formation of the 6-bromo-sugar 36, followed by formation of the hex-5-enopyranoside 37. Hydroboration of 37 stereoselectively afforded 38, followed by catalytic hydrogenation and trifluoroacetylation to give 19.
• Nakamura et al., Chemical and pharmaceutical bulletin, 1964, vol. 12, p. 1302,1306
  作者：Nakamura et al.

  DOI：——

  日期：——
• A convenient synthesis of 2-deoxy-d-arabino-hexose and of its methyl and benzyl glycosides
  作者：Claude Monneret、Patrick Choay

  DOI：10.1016/s0008-6215(00)81880-7

  日期：1981.10