1,6-anhydro-2-O-benzyl-3-deoxy-β-D-erythro-hexopyrano-4-ulose | 123823-24-5

• 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: 1,6-anhydro-2-O-benzyl-3-deoxy-β-D-erythro-hexopyrano-4-ulose
• 英文别名: 1,6-anhydro-2-O-benzyl-3-deoxy-D-erythro-hexopyrano-4-ulose；1,6-Anhydro-2-O-benzyl-3-deoxy-D-erythro-hexopyranos-4-ulose；(1R,4R,5R)-4-phenylmethoxy-6,8-dioxabicyclo[3.2.1]octan-2-one
• CAS: 123823-24-5
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: JZVDFDFIJWWASV-JHJVBQTASA-N

物化性质

• 沸点：
  371.7±42.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,6-anhydro-2-O-benzyl-3-deoxy-β-D-erythro-hexopyrano-4-ulose 在 palladium on activated charcoal chromium dichloride 、 dimethyl sulfide borane 、 四丁基氟化铵 、 氢气 、 氧气 、 nickel dichloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 六甲基磷酰三胺 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2S,4R)-2-[(R)-((1S,2S,3S,4R,5R)-3,4-Dihydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-hydroxy-methyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Convergent synthesis of (1→2)- and (1→4)-C-linked imino disaccharides†

  摘要：

  通过将羟脯氨酸衍生的甲醛与异左旋葡烯酮或左旋葡烯酮衍生的烯醇三酸酯进行野崎岸偶联，实现了(1â2)-和(1â4)-C-连接的亚氨基二糖的聚合合成。

  DOI：

  10.1039/a905310g
• 作为产物：
  描述：

  戊二酰-2-(羟甲基)蒽并醌 在 lithium aluminium tetrahydride 、 草酰氯 、 dimsylsodium 、 sodium acetate 、 二甲基亚砜 、 三乙胺 、 palladium dichloride 作用下， 以 乙醚 、 水 、 溶剂黄146 为溶剂， 反应 3.75h， 生成 1,6-anhydro-2-O-benzyl-3-deoxy-β-D-erythro-hexopyrano-4-ulose
  参考文献：
  名称：

  Synthesis of 3,6-dideoxy-4-C-(41-hydroxyethyl)hexopyranoses (yersinioses) from 1,6-anhydro-β-d-glucopyranose

  摘要：

  A series of isomers of 3,6-dideoxy-4-C-(4(1)-hydroxyethyl)-D-hexopyranose (yersiniose), structural components of the O-specific polysaccharides from the Yersinia genus, have been synthesised from 1,6-anhydro-beta-D-glucopyranose (levoglucosan).

  DOI：

  10.1016/s0008-6215(00)90496-8

文献信息

• Short, Stereoselective Syntheses of C(1→3)-linked Disaccharides
  作者：Yao-Hua Zhu、Pierre Vogel

  DOI：10.1016/s0040-4039(97)10460-9

  日期：1998.1

  Nucleophilic additions to D-isolevoglucosenone are face selective and generate the corresponding enolates which react with 1,2:3,4-di-O-isopropylidene-alpha-D-galacto-hexodialdo-1,5-pyranose to give aldol adducts. These can be reduced stereoselectively into C(1-->3) glycosides of 1,6-anhydro-D-galacto-pyranose. (C) 1997 Elsevier Science Ltd. All rights reserved.
• Convergent syntheses of C(1→3)-linked disaccharides starting from isolevoglucosenone
  作者：Yao-Hua Zhu、Raynald Demange、Pierre Vogel

  DOI：10.1016/s0957-4166(99)00492-9

  日期：2000.1

  Nucleophilic addition (Nu-Mf) to isolevoglucosenone 1 generates enolates stereospecifically (exo face addition) that can be reacted with sugar-derived aldehydes to give C(1-->3)-linked disaccharide precursors with high diastereoselectivity. Limitations of the method arising from unfavorable aldolate stability can be overcome by using Et2AlI as the nucleophile. This leads to products of Baylis-Hillmann condensations. One example is presented and has led to the preparation of 2,3-anhydro-3-C-[(1S)-2,6-anhydro-D-glycero-D-gulo-heptitol-1-C-yl]-beta-D-gulo-pyranose 5. (C) 2000 Elsevier Science Ltd. All rights reserved.
• C(1→4)-linked disaccharides through carbonylative Stille cross-coupling
  作者：Peter Steunenberg、Vincent Jeanneret、Yao-Hua Zhu、Pierre Vogel

  DOI：10.1016/j.tetasy.2004.11.048

  日期：2005.1

  A tinglucal tributyl[4,6-O-bis(t-butyl)silylidene-3-O-tris(isopropyl)silyl]tin 7 and a triflate derived from isolevoglucosenone (1R,4R,5R)-4-benzyloxy-6,8-dioxabicyclo[3.2.1]oct-2-en-2-yl trifluoromethanesulfonate 10 undergo the carbonylative Stille condensation under special conditions requiring AsPh3, LiCl, and powdered charcoal as co-catalysts to give a cross-conjugated dienone 6 in which the bicyclic alkene moiety is more reactive than the glucal alkene moiety. This allows the regio- and stereoselective hydrogenation of the bicyclic alkene moiety giving an enone 21 that can be reduced stereoselectively to an allylic alcohol 22. Hydroboration of the glucal and bicyclic acetal opening generates a C(1-->4) linked disaccharide 25 in which a protected form of beta-D-glucopyranose is attached at position C(4) of a alpha-D-3-deoxy-ribo-hexopyranoside derivative via a (S)-hydroxymethano linker. (C) 2004 Elsevier Ltd. All rights reserved.
• Short and Convergent Synthesis of (1→3)-C-Linked Imino Disaccharides (Aza-C-disaccharides)
  作者：Yao-Hua Zhu、Pierre Vogel

  DOI：10.1021/jo981781d

  日期：1999.1.1
• Synthesis of (<i>Z</i>)-3-Deoxy-3-(1,2,3,6-Tetradeoxy-3,6-Imino-L-<i>Arabino</i>-Hexitol-1-<i>C</i>-Ylidene)-D-<i>Xylo</i>-Hexose Derivatives. First Examples Of Homo-(1→3)-<i>C</i>-Linked Iminodisaccharides.
  作者：Francesca Cardona、Inmaculada Robina、Pierre Vogel

  DOI：10.1080/07328300008544099

  日期：2000.1

  Cross-aldolisation of 3,6-[(tert-butoxy)carbonyl]imino-2,3,6-trideoxy-4,5-O- isopropylidene-L-arabino-hexose (10) with 1,6-anhydro-2-O-benzyl-3-deoxy-beta-D-erythro-hexopyrano-4-ulose (6) generates, after water elimination, a single enone II that is reduced selectively into an allylic alcohol 12, deprotection of which affords methyl (Z)-3-deoxy-3-(1,2,3,6-tetradeoxy-3,6-imino-L-arabino-hexitol-1-C-ylidene)-beta-D-xylo-hexofuranoside (1) and (Z)-1,6-anhydro-3-deoxy-3-(1,2,3,6-tetradeoxy-3,6-imino-L-arabino-hexitol-1 -C-ylidene)-beta-D-xylo-hexopyranose (14).