2,3,4,6-tetra-O-benzyl-L-altrono-1,5-lactone | 167904-07-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-L-altrono-1,5-lactone
• 英文别名: (3R,4S,5S,6S)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-one
• CAS: 167904-07-6
• 化学式: C₃₄H₃₄O₆
• 分子量: 538.64
• InChiKey: BUBVLQDEIIUIQG-ZWDYZTTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  2,3,4,6-tetra-O-benzyl-L-altrono-1,5-lactone 在 二异丁基氢化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.33h， 以98%的产率得到2,3,4,6-tetra-O-benzyl-L-altrose
  参考文献：
  名称：

  A Novel and Practical Synthesis of l-Hexoses from d-Glycono-1,5-lactones

  摘要：

  A novel and efficient conversion of D-glycono-1,5-lactones into the corresponding L-sugars is described. The important intermediate, delta-hydroxyalkoxamates, was provided by a practical alkoxyamination of D-glycono-1,5-lactones mediated by Me3Al. In contrast to the preparation of beta-lactam skeletons from beta-hydroxyalkoxamates, the cyclization of delta-hydroxyalkoxamates under Mitsunobu conditions resulted in O-alkylation rather than N-alkylation. It is noteworthy that delta-hydroxyalkoxamates derived from D-mannono-1,5-lactones afforded the O-alkylation product in 91% yield. None of the N-alkylation product was detected in this case. These O-cyclized oximes, in which the inversion of the configuration at C5 was secured, were efficiently converted into the L-sugars.

  DOI：

  10.1021/ja992808t
• 作为产物：
  描述：

  苄氧基乙醛 在 四氧化锇 、 三氟乙酸 、 L-脯氨酸 N-甲基吲哚酮 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 生成 2,3,4,6-tetra-O-benzyl-L-altrono-1,5-lactone
  参考文献：
  名称：

  聚酮化合物和碳水化合物合成子的直接一锅高对映选择性组装

  摘要：

  提出了一种短，直接，催化，对映选择性合成聚酮化合物链段和碳水化合物的方法。新颖，直接，一锅，有机催化的不对称串联双羟醛/ Horner-Wittig-Emmons反应以93-98％ee的高收率组装了聚酮化合物和碳水化合物衍生物。将一锅催化不对称串联反应应用于稀有碳水化合物l-altrose的高度对映选择性形式从头合成。

  DOI：

  10.1016/j.tetlet.2006.05.018

文献信息

• Intramolecular Tishchenko Reactions of Protected Hexos-5-uloses: a Novel and Efficient Synthesis of l-Idose and l-Altrose
  作者：M. Adinolfi、G. Barone、F. De Lorenzo、A. Iadonisi

  DOI：10.1055/s-1999-3156

  日期：1999.3

  Protected t-butyl esters of aldonic acids with the rare L-ido and L-altro configuration can be effectively obtained by a diastereoselective Tishchenko reaction of hexos-5-uloses induced by t-BuOSmI2. These compounds can be easily converted into the corresponding protected lactones and free sugars.

  可以通过t-BuOSmI2诱导的六碳糖5-酮糖的立体选择性Tishchenko反应，有效地获得具有稀有L-ido和L-altro构象的戊酸的保护叔丁基酯。这些化合物可以容易地转化为相应的保护内酯和游离糖。
• Synthesis of Galactose- andN-Acetylglucosamine-Derived Tetrazoles and their evaluation as ?-glycosidase inhibitors
  作者：Thomas D. Heightman、Philipp Ermert、Daniela Klein、Andrea Vasella

  DOI：10.1002/hlca.19950780221

  日期：1995.3.22

  NaN3 yielded the tetrazole 25, which was deprotected to 6. The tetrabenzyl ether 16 (from 14, or from 25via27) was reduced to 28 and deprotected to give the known deoxygalactostain 8 (Scheme 2). Oxidation of the hydroxynitrile 30, derived from 29, followed by reduction of 32 yielded mostly the L-ido-hydroxynitrile (Scheme 3), which was tosylated and treated with NaN3 to give the tetrazole 35a and its manno-isomer

  标题化合物6和7已经从已知的2,3-二-制备ø -苄基-4,6- ø -亚苄基- d -半乳糖（18）和Ñ 2 -乙酰基三- ö苄基D-氨基葡萄糖肟（29）分别分八步和六步进行。由14制备导致苄基化的半乳糖-四唑16的叠氮腈，并在其形成的条件下使其环化（方案1）。通过氧化10得到醇13其次是减少。当将亚苄基保护的D-半乳糖醇20进行氧化还原时，经由酮21产生L- α-醇22（方案2），实现了更好的产率和非对映选择性。用NaN 3处理相应的甲苯磺酸酯24，得到四唑25，将其脱保护为6。四苄基醚16（从14或从25通过27）还原为28并脱保护得到已知的脱氧半乳糖苷8（方案2）。氧化衍生自29的羟基腈30，然后还原32，主要生成L- ido-羟基腈（流程3），将其甲苯磺酸化并用NaN 3处理，得到四唑35a及其甘露糖异构体36a，而Al （N 3）3产生（E）-和（Z）-38（方案4）。中间叠氮化物39当使用NH
• A Novel and Practical Synthesis of <scp>l</scp>-Hexoses from <scp>d</scp>-Glycono-1,5-lactones
  作者：Hideyo Takahashi、Yuko Hitomi、Yoshinori Iwai、Shiro Ikegami

  DOI：10.1021/ja992808t

  日期：2000.4.1

  A novel and efficient conversion of D-glycono-1,5-lactones into the corresponding L-sugars is described. The important intermediate, delta-hydroxyalkoxamates, was provided by a practical alkoxyamination of D-glycono-1,5-lactones mediated by Me3Al. In contrast to the preparation of beta-lactam skeletons from beta-hydroxyalkoxamates, the cyclization of delta-hydroxyalkoxamates under Mitsunobu conditions resulted in O-alkylation rather than N-alkylation. It is noteworthy that delta-hydroxyalkoxamates derived from D-mannono-1,5-lactones afforded the O-alkylation product in 91% yield. None of the N-alkylation product was detected in this case. These O-cyclized oximes, in which the inversion of the configuration at C5 was secured, were efficiently converted into the L-sugars.
• Direct one-pot highly enantioselective assembly of polyketide and carbohydrate synthons
  作者：Gui-Ling Zhao、Wei-Wei Liao、Armando Córdova

  DOI：10.1016/j.tetlet.2006.05.018

  日期：2006.7

  short, direct, catalytic, enantioselective synthesis of polyketide segments and carbohydrates is presented. The novel, direct, one-pot, organocatalytic asymmetric tandem cross-aldol/Horner–Wittig–Emmons reactions assemble polyketide and carbohydrate derivatives in good yield with 93–98% ee. The one-pot catalytic asymmetric tandem reaction was applied to a highly enantioselective formal de novo synthesis

  提出了一种短，直接，催化，对映选择性合成聚酮化合物链段和碳水化合物的方法。新颖，直接，一锅，有机催化的不对称串联双羟醛/ Horner-Wittig-Emmons反应以93-98％ee的高收率组装了聚酮化合物和碳水化合物衍生物。将一锅催化不对称串联反应应用于稀有碳水化合物l-altrose的高度对映选择性形式从头合成。