methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-altro-heptopyranoside | 68027-31-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-altro-heptopyranoside
• 英文别名: METHYL 2,3,4-TRI-O-BENZYL-6-DEOXY-α-D-GLUCOHEPTOPYRANOSIDE；2-((2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)ethanol；methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-manno-heptopyranoside；methyl 6-deoxy-2,3,4-tri-O-benzyl-α-D-manno-heptopyranoside；methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-mannoheptopyranoside；1-O-methyl-2,3,4-tri-O-benzyl-6-deoxy-D-mannoheptopyranose
• CAS: 68027-31-6；133918-92-0；40653-18-7
• 化学式: C₂₉H₃₄O₆
• 分子量: 478.585
• InChiKey: IMIUUOMKTPBICJ-PNHLWVRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35.0
• 可旋转键数：
  12.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-altro-heptopyranoside 在 N,N-二异丙基乙胺 、 lithium bromide 作用下， 以 二氯甲烷 、 丁酮 为溶剂， 反应 1.25h， 生成 methyl 2,3,4-tri-O-benzyl-6-deoxy-7-bromo-α-D-mannoheptopyranoside
  参考文献：
  名称：

  A Flexible Route to Mannose 6-Phosphonate Functionalized Derivatives

  摘要：

  A new approach for the synthesis of a mannose 6-phosphonate isosteric analog of mannose 6-phosphate is reported. The mannosylphosphonate has been prepared in a multistep synthesis involving an homologation reaction of the methyl alpha-D-mannopyranoside followed by an Arbuzov reaction between a bromohomomannosyl derivative and the tris(trimethylsilyl)phosphite. This approach, avoiding the deprotection of dialkylphosphonate, allowed us to prepare the mannose 6-phosphonate in good yield. The described method was successfully extended to the preparation of a mannose 6-phosphonate linked to a cholesteryl moiety. This strategy affords a more general route for a wide range of functionalized mannose 6-phosphonate derivatives.

  DOI：

  10.1080/10426500214297
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-deoxy-6-(1,3-dithianyl)-α-D-mannopyranoside 在 sodium tetrahydroborate 、 ammonium cerium(IV) nitrate 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 0.33h， 生成 methyl 2,3,4-tri-O-benzyl-6-deoxy-α-D-altro-heptopyranoside
  参考文献：
  名称：

  A Flexible Route to Mannose 6-Phosphonate Functionalized Derivatives

  摘要：

  A new approach for the synthesis of a mannose 6-phosphonate isosteric analog of mannose 6-phosphate is reported. The mannosylphosphonate has been prepared in a multistep synthesis involving an homologation reaction of the methyl alpha-D-mannopyranoside followed by an Arbuzov reaction between a bromohomomannosyl derivative and the tris(trimethylsilyl)phosphite. This approach, avoiding the deprotection of dialkylphosphonate, allowed us to prepare the mannose 6-phosphonate in good yield. The described method was successfully extended to the preparation of a mannose 6-phosphonate linked to a cholesteryl moiety. This strategy affords a more general route for a wide range of functionalized mannose 6-phosphonate derivatives.

  DOI：

  10.1080/10426500214297

文献信息

• Synthesis, Characterization, and Coupling Reactions of Six-Membered Cyclic P-Chiral Ammonium Phosphonite–Boranes; Reactive <i>H</i>-Phosphinate Equivalents for the Stereoselective Synthesis of Glycomimetics
  作者：Angélique Ferry、Xavier Guinchard、Pascal Retailleau、David Crich

  DOI：10.1021/ja305104b

  日期：2012.7.25

  phostone-mimetics of disaccharides. On the basis of these studies, successful protocols were established for the synthesis of β-gluco and α- and β-manno-configured phostones of primary alcohols. Deprotection of the dimeric compounds leads to novel families of α- or β-(1→6)-linked glycomimetics.

  葡萄糖和甘露糖系列中 P-手性亚膦酸铵-硼烷配合物的立体选择性合成已从 P(V) 膦衍生物发展而来。已经研究了这些光酮供体与醇的偶联反应，特别强调保护基团和条件对立体选择性的影响。亚膦酸酯-硼烷复合物可直接用于偶联反应，产物原位氧化以得到二糖的磷酮模拟物。在这些研究的基础上，建立了合成 β-葡萄糖和 α- 和 β- 甘露糖构型伯醇的成功方案。二聚体化合物的去保护导致了新的α-或β-(1→6)-连接的糖模拟物家族。
• Syntheses of methyl glycosides of 6-deoxyheptoses
  作者：Gerald O. Aspinall、Armando G. McDonald、Ramesh K. Sood

  DOI：10.1139/v94-037

  日期：1994.1.1

  by reduction of the resulting heptopyranosidurononitriles with diisobutylaluminum hydride, hydrolysis of the imine, further reduction with sodium borohydride, and catalytic O-debenzylation, give the corresponding methyl 6-deoxyheptopyranosides. Configurational change at C-4 of methyl 6-deoxy-7-O-tert-butyldiphenylsilyl-α-D-manno-heptopyranoside to give the talo isomer was effected by oxidation followed

  已经制备了 6-脱氧-D-altro-heptose、6-deoxy-D-manno-heptose 和 6-deoxy-D-talo-heptose 的甲基 α-D-glycopyranosides。用氰化钾置换 2,3,4-三-O-苄基己基己基吡喃糖苷 6-三氟甲磺酸甲酯，然后用二异丁基氢化铝还原生成的吡喃基吡喃糖醛腈，水解亚胺，用硼氢化钠进一步还原，并催化 O-脱苄基，得到相应的甲基 6-脱氧庚基吡喃糖苷。甲基 6-脱氧-7-O-叔丁基二苯基甲硅烷基-α-D-甘露-吡喃庚糖苷在 C-4 处的构型变化以得到 talo 异构体是通过氧化和立体选择性还原来实现的。苷的1H核磁共振数据，
• Access to 6-Deoxy-heptose Constructs by One Carbon Homologation of Hexoses with Malononitrile: Divergent Synthesis of <i>Campylobacter jejuni</i> Strain 81-176 Capsular Trisaccharide Repeating Unit Derivatives
  作者：Yao Sun、Zhi Qiao、Dongwei Li、Jingxuan Ni、Jianjun Wang、Peng Wang、Ni Song、Ming Li

  DOI：10.1021/acs.orglett.2c03075

  日期：2022.11.4

  efficient approach to 6-deoxy-heptose constructs has been established by one-carbon homologation of the sugar chain of hexoses. The reaction features the formation of sugar-based α-substituted propanedinitriles and ensuing diverse oxidative transformations under mild reaction conditions that are compatible with a wide range of sugars bearing various functional/protecting groups. The applications of this

  已经通过己糖糖链的单碳同源建立了 6-脱氧-庚糖构建体的有效方法。该反应的特点是在温和的反应条件下形成糖基 α-取代的丙二腈并随后发生多种氧化转化，这些反应与带有各种功能/保护基团的各种糖相容。这种方法的应用通过空肠弯曲杆菌菌株 81-176 荚膜三糖重复单元衍生物的发散组装得到证明。
• General Homologation Strategy for Synthesis of <scp>l</scp>-<i>glycero</i>- and <scp>d</scp>-<i>glycero</i>-Heptopyranoses
  作者：Shaheen K. Mulani、Kuang-Chun Cheng、Kwok-Kong T. Mong

  DOI：10.1021/acs.orglett.5b02620

  日期：2015.11.20

  A general and stereospecific homologation strategy for the synthesis of heptopyranosides is reported. The strategy employs the Wittig olefination and proline-catalyzed a-aminoxylation to achieve one carbon elongation and stereoselective hydroxylation at the C6 position, respectively. The l-glycero- and d-glycero-heptopyranosides can be obtained with nearly perfect stereoselectivity. Further study reveals the difference in the chemical shift of the C6 proton of l/d-glycero-heptopyranosyl diastereomers, which is found to be useful for assignment of the configuration of heptopyranosides.
• EP2017281
  申请人：——

  公开号：——

  公开（公告）日：——