1,5-anhydro-2,6-dideoxy-3-O-<(4-methoxyphenyl)methyl>-D-lyxo-hex-1-enopyranoside | 134355-02-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,5-anhydro-2,6-dideoxy-3-O-<(4-methoxyphenyl)methyl>-D-lyxo-hex-1-enopyranoside
• 英文别名: (2R,3S,4R)-4-[(4-methoxyphenyl)methoxy]-2-methyl-3,4-dihydro-2H-pyran-3-ol
• CAS: 134355-02-5
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: LNJBPUMHTYASBI-HONMWMINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-2,6-dideoxy-3-O-<(4-methoxyphenyl)methyl>-D-lyxo-hex-1-enopyranoside 在 吡啶 、 偶氮二异丁腈 、 iodonium(di-γ-collidine) perchlorate 、 4 A molecular sieve 、 三苯基氢化锡 、 二甲基二环氧乙烷 、 sodium hydride 作用下， 以 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 10.75h， 生成 methyl 4,6-dideoxy-4-<<(2,4,6-trideoxy-3-O<(1,1-dimethylethyl)dimethylsilyl>-4-(methylthio)-β-D-ribo-hexopyranosyl)oxy><2-(trimethylsilyl)ethoxycarbonyl>amino>-2-O-<2,4-dideoxy-3-O-methyl-4-phthalimido-α-L-threo-pentopyranosyl>-3-O-(4-methoxyphenyl)..
  参考文献：
  名称：

  Studies Related to the Carbohydrate Sectors of Esperamicin and Calicheamicin: Definition of the Stability Limits of the Esperamicin Domain and Fashioning of a Glycosyl Donor from the Calicheamicin Domain

  摘要：

  The core trisaccharide regions of esperamicin and the aryltetrasaccharide region of calicheamicin have been synthesized. The minimum protection modalities necessary to stabilize structures against rearrangement to an isomeric azafuranose series were ascertained (see compounds 12 and 65). Deprotection of the 2-(trimethylsilyl)ethoxycarbonyl carbamate from 65 led to azafuranose 14 characterized as methyl glycoside 15. Using this insight, it was possible to fashion, for the first time, a pre-glycosyl donor (see compound 128) corresponding to the complete arylsaccharide sector of calicheamicin gamma(1)(I) at the oxidation level of the domain. Among the key assembly strategies were the conversion of alpha-thiophenylpseudoglycals to allal derivatives (see 44 --> 45); the interfacing of epoxide-mediated glycosylation with iodoglycosylation (see 30 --> 47 --> 48); the synthesis of hydroxylamine glycosides via triflate displacement (see 61 + 91 --> 101); and a new route to p-hydroxybenzonitriles (see formation of 86).

  DOI：

  10.1021/ja00126a013
• 作为产物：
  描述：

  3,4-di-O-acetyl-D-fucal 在 sodium methylate 、 二正丁基氧化锡 、 cesium fluoride 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 1,5-anhydro-2,6-dideoxy-3-O-<(4-methoxyphenyl)methyl>-D-lyxo-hex-1-enopyranoside
  参考文献：
  名称：

  Studies Related to the Carbohydrate Sectors of Esperamicin and Calicheamicin: Definition of the Stability Limits of the Esperamicin Domain and Fashioning of a Glycosyl Donor from the Calicheamicin Domain

  摘要：

  The core trisaccharide regions of esperamicin and the aryltetrasaccharide region of calicheamicin have been synthesized. The minimum protection modalities necessary to stabilize structures against rearrangement to an isomeric azafuranose series were ascertained (see compounds 12 and 65). Deprotection of the 2-(trimethylsilyl)ethoxycarbonyl carbamate from 65 led to azafuranose 14 characterized as methyl glycoside 15. Using this insight, it was possible to fashion, for the first time, a pre-glycosyl donor (see compound 128) corresponding to the complete arylsaccharide sector of calicheamicin gamma(1)(I) at the oxidation level of the domain. Among the key assembly strategies were the conversion of alpha-thiophenylpseudoglycals to allal derivatives (see 44 --> 45); the interfacing of epoxide-mediated glycosylation with iodoglycosylation (see 30 --> 47 --> 48); the synthesis of hydroxylamine glycosides via triflate displacement (see 61 + 91 --> 101); and a new route to p-hydroxybenzonitriles (see formation of 86).

  DOI：

  10.1021/ja00126a013

文献信息

• Stereoselective Synthesis of 2-Deoxy-β-glycosides Using Anomeric O-Alkylation/Arylation
  作者：William J. Morris、Matthew D. Shair

  DOI：10.1021/ol8022006

  日期：2009.1.1

  Anomeric O-alkylation/arylation is applied to the synthesis of 2-deoxy-β-glycosides. Treatment of lactols with NaH in dioxane followed by the addition of electrophiles leads to the formation of 2-deoxy-β-glycosides in high yield and high selectivity. The high β-selectivity observed here demonstrates a powerful stereoelectronic effect for the stereoselective formation of acetals under kinetic control

  异头 O-烷基化/芳基化应用于 2-脱氧-β-糖苷的合成。在二恶烷中用 NaH 处理乳糖醇，然后加入亲电子试剂，以高产率和高选择性形成 2-脱氧-β-糖苷。这里观察到的高β-选择性证明了在动力学控制下立体选择性形成缩醛的强大立体电子效应。
• Observations in the Chemistry and Biology of Cyclic Enediyne Antibiotics:  Total Syntheses of Calicheamicin γ₁^I and Dynemicin A
  作者：Samuel J. Danishefsky、Matthew D. Shair

  DOI：10.1021/jo951560x

  日期：1996.1.1
• The synthesis of the core trisaccharide of esperamicin: corroboration of the proposed structure for its rearrangement product and stabilization of the core trisaccharide domain
  作者：Randall L. Halcomb、Mark D. Wittman、Steven H. Olson、Samuel J. Danishefsky、Jerzy Golik、Henry Wong、Dolatrai Vyas

  DOI：10.1021/ja00013a065

  日期：1991.6
• Direct Synthesis of 2-Deoxy-β-Glycosides via Anomeric <i>O</i>-Alkylation with Secondary Electrophiles
  作者：Danyang Zhu、Kedar N. Baryal、Surya Adhikari、Jianglong Zhu

  DOI：10.1021/ja4116956

  日期：2014.2.26

  An approach for direct synthesis of biologically significant 2-deoxy-beta-glycosides has been developed via O-alkylation of a variety of 2-deoxy-sugar-derived anomeric alkoxides using challenging secondary triflates as electrophiles. It was found a free hydroxyl group at C3 of the 2-deoxy-sugar-derived lactols is required in order to achieve synthetically efficient yields. This method has also been applied to the convergent synthesis of a 2-deoxy-beta-tetrasaccharide.
• HALCOMB, RANDALL L.;WITTMAN, MARK D.;OLSON, STEVEN H.;DANISHETSKY, SAMUEL+, J. AMER. CHEM. SOC., 113,(1991) N3, C. 5080-5082
  作者：HALCOMB, RANDALL L.、WITTMAN, MARK D.、OLSON, STEVEN H.、DANISHETSKY, SAMUEL+

  DOI：——

  日期：——