2-[(3R,4R,5S,6R)-2-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione | 125946-77-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(3R,4R,5S,6R)-2-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione
• CAS: 125946-77-2
• 化学式: C₃₅H₃₃NO₇
• 分子量: 579.65
• InChiKey: IUFLCZSXWOOQTF-MOMIRWHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  94.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[(3R,4R,5S,6R)-2-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione 生成 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl trichloroacetimidate
  参考文献：
  名称：

  YAMAZAKI, FUMITO;KITAJIMA, TOHRU;NUKADA, TOMOO;ITO, YUKISHIGE;OGAWA, TOMO+, CARBOHYDR. RES. , 201,(1990) N, C. 15-30

  摘要：

  DOI：
• 作为产物：
  描述：

  allyl 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 sodium acetate 、 溶剂黄146 、 potassium iodide 、 palladium dichloride 、 silver(l) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 2-[(3R,4R,5S,6R)-2-hydroxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]isoindole-1,3-dione
  参考文献：
  名称：

  Synthesis of an appropriately protected core glycotetraoside, a key intermediate for the synthesis of “bisected” complex-type glycans of a glycoprotein

  摘要：

  A stereocontrolled synthetic route to a glycotetraoside, allyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1--- -4)-O- (3,6-di-O-allyl-2-O-benzyl-beta-D-mannopyranosyl)-(1----4)-O-3, 6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4)-3-O- benzyl- 2-deoxy-6-O-p-methoxy-phenyl-2-phthalimido-beta-D-glucopyranoside, an important intermediate for the synthesis of "bisected" complex type glycans of glycoproteins has been established by employing two glycosyl donors, 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate and 4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-alpha-D-mannopyranosyl bromide, and a glycosyl acceptor, allyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4) -3-O- benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-beta-D-glucopyranoside.

  DOI：

  10.1016/0008-6215(90)84222-g

文献信息

• Ketone-Imide versus Ketone-Oxime Reductive Cross-Coupling Promoted by Samarium Diiodide:  New Mechanistic Insight Gained from a Failed Aminocyclopentitol Synthesis
  作者：Jose Luis Chiara、Ángela García、Gabriella Cristóbal-Lumbroso

  DOI：10.1021/jo050185y

  日期：2005.5.1

  6-ketone/imide reductive coupling promoted by samarium diiodide competes favorably with an alternative 1,5-ketone/oxime ether coupling in a keto-oxime substrate derived from d-glucosamine N-protected with a phthalimido group. This pinacol coupling reaction affords new homochiral α-hydroxylactam scaffolds that could be useful in diversity-oriented synthesis. A mechanistic proposal for this reaction that explains

  由二碘化promote促进的分子内1,6-酮/酰亚胺还原偶联与衍生自被邻苯二甲酰亚胺基保护的d-葡糖胺N-的酮肟肟底物与替代的1,5-酮/肟醚偶联具有竞争优势。频哪醇偶联反应提供了新的高手性α-羟基内酰胺支架，可用于面向多样性的合成。DFT量子力学计算对模型化合物的解释为该反应提供了解释实验结果的机制建议。
• Synthesis of the <i>Campylobacter jejuni</i> 81 <b>‐</b> 176 Strain Capsular Polysaccharide Repeating Unit Reveals the Absolute Configuration of its <i>O</i> ‐Methyl Phosphoramidate Motif
  作者：V. Narasimharao Thota、Michael J. Ferguson、Ryan P. Sweeney、Todd L. Lowary

  DOI：10.1002/anie.201810222

  日期：2018.11.19

  the absolute stereochemistry at this atom has been undefined. We report the synthesis of the three repeating units found in C. jejuni 81‐176 CPS; one of these possesses a MeOPN group. In the course of these studies we established that the stereochemistry of the phosphorus atom in this MeOPN group is R. These studies represent the first unequivocal proof of stereochemistry of this group in any C. jejuni

  所述Ô甲基氨基磷酸酯（MeOPN）基序在所有的≈70％荚膜多糖（CPS）的一个非化学计量的修改空肠弯曲菌菌株。空肠弯曲杆菌的感染导致食源性疾病，它们产生的CPS是关键的毒力因子。这些CPS中的MeOPN磷原子是立体异构的，是单一的立体异构体。然而，迄今为止，该原子的绝对立体化学尚未确定。我们报告了空肠弯曲杆菌81-176 CPS中三个重复单元的合成；其中之一拥有MeOPN小组。在这些研究过程中，我们确定了该MeOPN基团中磷原子的立体化学是R。这些研究代表了空肠弯曲杆菌CPS中该组立体化学的第一个明确证据。预期所产生的化合物将是针对这种结构有趣的修饰的功能和生物合成进行研究的有用工具，到目前为止，这种修饰仅在弯曲杆菌中才能鉴定出来。
• Expedient and Versatile Formation of Novel Amino-deoxy-ketoheptuloses
  作者：Yevgeniy Leshch、Anna Jacobsen、Julian Thimm、Joachim Thiem

  DOI：10.1021/ol4021699

  日期：2013.10.4

  Novel monoketoheptuloses have been synthesized employing an amination step in a pre- and/or post-C1 chain elongation using a Petasis reagent by starting from aldohexoses or aldohexosamines. A series of gluco and manno configured 1-/3-deoxy-1-/3-amino-ketohept-2-uloses could be obtained.
• YAMAZAKI, FUMITO;KITAJIMA, TOHRU;NUKADA, TOMOO;ITO, YUKISHIGE;OGAWA, TOMO+, CARBOHYDR. RES. , 201,(1990) N, C. 15-30
  作者：YAMAZAKI, FUMITO、KITAJIMA, TOHRU、NUKADA, TOMOO、ITO, YUKISHIGE、OGAWA, TOMO+

  DOI：——

  日期：——
• Synthesis of an appropriately protected core glycotetraoside, a key intermediate for the synthesis of “bisected” complex-type glycans of a glycoprotein
  作者：Fumito Yamazaki、Tohru Kitajima、Tomoo Nukada、Yukishige Ito、Tomoya Ogawa

  DOI：10.1016/0008-6215(90)84222-g

  日期：1990.6

  A stereocontrolled synthetic route to a glycotetraoside, allyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1--- -4)-O- (3,6-di-O-allyl-2-O-benzyl-beta-D-mannopyranosyl)-(1----4)-O-3, 6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4)-3-O- benzyl- 2-deoxy-6-O-p-methoxy-phenyl-2-phthalimido-beta-D-glucopyranoside, an important intermediate for the synthesis of "bisected" complex type glycans of glycoproteins has been established by employing two glycosyl donors, 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate and 4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-alpha-D-mannopyranosyl bromide, and a glycosyl acceptor, allyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4) -3-O- benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-beta-D-glucopyranoside.