2,3:5,6-di-O-isopropylidene-L-mannonic acid γ-lactone | 49561-21-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3:5,6-di-O-isopropylidene-L-mannonic acid γ-lactone
• 英文别名: 2,3;5,6-di-O-isopropylidene-D-gulonic acid γ-lactone；2,3:5,6-di-O-isopropylidene-D-gulono-1,4-lactone；(3aR,6S,6aR)-6-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one；O²,O³;O⁵,O⁶-diisopropylidene-L-mannonic acid-lactone；O²,O³;O⁵,O⁶-Diisopropyliden-L-mannonsaeure-lacton；(3aR,6S,6aR)-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• CAS: 49561-21-9
• 化学式: C₁₂H₁₈O₆
• 分子量: 258.271
• InChiKey: OFZPAXSEAVOAKB-RBXMUDONSA-N

物化性质

• 熔点：
  123-125 °C
• 沸点：
  361.2±42.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3:5,6-di-O-isopropylidene-L-mannonic acid γ-lactone 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 生成 (4R,5R)-5-[(S)-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-hydroxy-methyl]-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde
  参考文献：
  名称：

  Synthetic studies on halichondrins: A new practical synthesis of the C.1–C.12 segment

  摘要：

  A new practical synthesis of the C.1-C.12 halichondrin segment was achieved from L-mannonic gamma-lactone (5), using osmylation, C-allylation and Michael reaction as key steps.

  DOI：

  10.1016/s0040-4039(00)60394-5
• 作为产物：
  描述：

  D-galactono-1,4-lactone 以94%的产率得到
  参考文献：
  名称：

  BUCHANAN, J. GRANT;LUMBARD, KEITH W.;STURGEON, ROBERT J.;THOMPSON, DERYK +, J. CHEM. SOC. PERKIN TRANS. PT 1,(1990) N, C. 699-706

  摘要：

  DOI：

文献信息

• A convenient strategy for replacement of the anomeric hydroxyl group by difluoromethyl functionality in carbohydrate derivatives
  作者：J.Sarah Houlton、William B. Motherwell、Barry C. Ross、Matthew J. Tozer、David J. Williams、Alexandra M.Z. Slawin

  DOI：10.1016/s0040-4020(01)88029-7

  日期：1993.9

  A series of carbohydrate gem-difluoroenol ethers are readily prepared by the reaction of the corresponding lactones with dibromodifluoromethane, tris(dimethylamino)phosphine and zinc. Subsequent catalytic hydrogenation provides difluoromethyl C-glycoside analogues in which the exocyclic oxygen atom has been replaced by a difluoromethylene unit.

  通过使相应的内酯与二溴二氟甲烷，三（二甲基氨基）膦和锌反应，可以容易地制备一系列碳水化合物的宝石-二氟烯醇醚。随后的催化氢化提供了二氟甲基C-糖苷类似物，其中环外氧原子已被二氟亚甲基单元取代。
• All Eight Stereoisomeric <scp>d</scp>-Glyconic-δ-lactams:  Synthesis, Conformational Analysis, and Evaluation as Glycosidase Inhibitors
  作者：Yoshio Nishimura、Hayamitsu Adachi、Takahiko Satoh、Eiki Shitara、Hikaru Nakamura、Fukiko Kojima、Tomio Takeuchi

  DOI：10.1021/jo000141j

  日期：2000.8.1

  gamma-lactone to lead to two epimers of delta-lactam from one parent gamma-lactone. Conformations of eight glycono-delta-lactams were examined by X-ray crystallographic analysis and molecular modeling. Analyses of conformation and glycosidase-inhibition provide useful information for the design of new glycosidase inhibitors.

  已经开发了一种有效且通用的合成途径，用于合成所有八种立体异构D-糖基-δ-内酰胺。该策略包括作为关键步骤的立体发散性δ-内酰胺的形成，其具有构型保留或在起始C-内酰胺的C-4处反转，以从一个母体γ-内酯产生两种δ-内酰胺差向异构体。通过X射线晶体学分析和分子模型检查了八个糖基-δ-内酰胺的构象。构象和糖苷酶抑制分析为设计新型糖苷酶抑制剂提供了有用的信息。
• Short syntheses of D-deoxymannojirimycin and D-mannonolactam from L-gulonolactone and of L-deoxymannojirimycin and L-mannonolactam from D-gulonolactone
  作者：George W.J. Fleet、Nigel G. Ramsden、David R. Witty

  DOI：10.1016/0040-4039(88)85234-1

  日期：1988.1

  Short syntheses of D-deoxymannojirimycin and of D-mannonolactam from L-gulonolactone are reported; identical sequences on D-gulonolactone lead to L-deoxymannojirimycin and L-mannonolactam.

  据报道，由L-古洛内酯短合成D-脱氧甘露糖霉素和D-甘露内酰胺。D-古洛内酯上的相同序列导致L-脱氧甘露糖霉素和L-甘露糖内酰胺。
• The Formation of Polyhydroxy-dialdehydes. III.<i>l</i>-Lyxotrihydroxy-glutaric Dialdehyde and its Derivatives
  作者：Koichi Iwadare

  DOI：10.1246/bcsj.17.372

  日期：1942.8

  Following compounds were obtained in crystals: 2,3,5,6-Diacetone-l-mannofuranose, m.p., 122–122.5° and [α]D=−27° (in acetone). Bis-phenylhydrazone of l-lyxo-trihydroxy-glutaric dialdehyde, m.p., 165–165.5° and [α]D=+73° (in pyridine). Bis-p-nitro-phenyl-hydrazone of l-lyxotrihydroxy-glutaric dialdehyde, m.p., 203.5–204°. Potassium diacetone-l-mannonate, [α]D10=+32.2° (in water). And diacetone-l-mannopolactone, m.p. 124–124.5°.

  以下化合物为晶体：2,3,5,6-二丙酮-l-甘露糖，熔点 122-122.5°，[α]D=-27°（在丙酮中）。l-lyxo-trihydroxy-glutaric dialdehyde 的双苯基腙，熔点 165-165.5°，[α]D=+73°（在吡啶中）。l-lyxotrihydroxy-glutaric dialdehyde 的双对硝基苯腙，熔点 203.5-204°。二丙酮-l-甘露酸钾，[α]D10=+32.2°（水中）。二丙酮-l-甘露内酯，熔点 124-124.5°。
• A unified strategy for the synthesis of enantiomerically pure branched-chain cyclohexenones and -cyclopentenones from a single progenitor
  作者：F. Chrétien、M. Khaldi、Y. Chapleur

  DOI：10.1016/s0040-4039(97)01348-8

  日期：1997.8

  Branched-chain cyclohexenones and cyclopentenones were prepared from sugar lactones by amide enolate condensation and subsequent intramolecular Knoevenagel reaction. Depending on the conditions, either the six- or the five-membered rings can be prepared from the same progenitor

  由糖内酯通过酰胺烯酸酯缩合和随后的分子内Knoevenagel反应制备支链环己烯酮和环戊烯酮。根据条件，六元环或五元环可以由同一祖细胞制备