benzyl 4,6-O-benzylidene-2-amino-2-deoxy-α-D-glucopyranoside | 13347-83-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 4,6-O-benzylidene-2-amino-2-deoxy-α-D-glucopyranoside
• 英文别名: benzyl 4,6-O-benzylidene-2-amino-2-deoxy-α-D-glucoside；benzyl 2-amino-4,6-benzylidene-2-deoxy-α-D-glucopyranoside；benzyl 2-amino-4,6-O-benzylidene-2-deoxy-α-glucopyranoside；(4aR,6S,7R,8R,8aS)-7-amino-2-phenyl-6-phenylmethoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-ol
• CAS: 13347-83-6
• 化学式: C₂₀H₂₃NO₅
• 分子量: 357.406
• InChiKey: BOSPELTZTUYCQA-NPKOBNKKSA-N

物化性质

• 熔点：
  178-179 °C(Solv: chloroform (67-66-3); water (7732-18-5); ethanol (64-17-5))
• 沸点：
  551.0±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  83.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl 4,6-O-benzylidene-2-amino-2-deoxy-α-D-glucopyranoside 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 benzyl 4,6-O-benzylidene-2-benzyloxyacetamido-3-O-<1-(R)-carboxyethyl>-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  具有增强佐剂活性的胞壁酰二肽类似物的合成

  摘要：

  N-Acetylmuramyl-L-alanyl-D-isoglutamine (MDP) 和十三个新的类似物是通过常规有机化学方法合成的，使用二环己基碳二亚胺-N-羟基-5-降冰片烯-2,3-二甲酰亚胺作为偶联剂。测定了它们在豚鼠中诱导对 N-乙酰基-3-(4-arsonophenylazo)-L-酪氨酸的迟发型超敏反应的能力。结果表明，与 MDP 中乳酸部分相邻的 α-氨基酸的存在对于高生物活性很重要，缬氨酸类似物具有最有利的作用。讨论了构效关系。

  DOI：

  10.1246/bcsj.53.2570
• 作为产物：
  描述：

  D-GlcNAc 在 乙酰氯 、 potassium hydroxide 、 zinc(II) chloride 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 48.0h， 生成 benzyl 4,6-O-benzylidene-2-amino-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  糖衍生的氨基醇催化亚胺还原的方法

  摘要：

  本发明公开了一种糖衍生的氨基醇催化亚胺还原的方法：以亚胺为底物，依次包括以下步骤：1）、将亚胺和糖衍生的氨基醇催化剂溶于有机溶剂Ⅰ中，所述亚胺和糖衍生的氨基醇催化剂的摩尔比为100:1～20；2）、向步骤1）所得的溶液中滴加1.5～5倍当量的三氯硅烷后，于-20～40℃下搅拌反应12～36h后，然后用饱和碳酸氢钠溶液淬灭；3）、将步骤2）的所得物用有机溶剂Ⅱ萃取，柱层析分离，制得胺类化合物。

  公开号：

  CN103936596B
• 作为试剂：
  描述：

  1-苄基-1H-吲哚-2,3-二酮 、 丙酮 在 benzyl 4,6-O-benzylidene-2-amino-2-deoxy-α-D-glucopyranoside 作用下， 以 二氯甲烷 为溶剂， 反应 24.25h， 生成 (R)-1-benzyl-3-hydroxy-3-(2'-oxopropyl)indolin-2-one 、 (S)-1-benzyl-3-hydroxy-3-(2-oxopropyl)indolin-2-one
  参考文献：
  名称：

  Carbohydrate-derived alcohols as organocatalysts in enantioselective aldol reactions of isatins with ketones

  摘要：

  The catalytic activity of carbohydrate-derived amino alcohols in the enantioselective aldol reaction of ketones with isatin and its derivatives has been examined for the first time. The carbohydrate-derived amino alcohols 5 were found to be efficient organocatalysts for asymmetric aldol reactions. A variety of isatins were used as substrates and the corresponding aldol products were obtained in high yields (up to 99%) and with moderate enantioselectivities (up to 75%). Crown Copyright (C) 2011 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.04.007

文献信息

• Muramyl Peptides, 1 Stereochemically Pure Derivatives of Muramic and Isomuramic Acids
  作者：Paul H. Gross、Manfred Rimpler

  DOI：10.1002/jlac.198619860104

  日期：1986.1.14

  of their methyl esters (4r and 4s). The high yield and complete separation of 4r and 4s allow a reliable assessment of the low stereoselectivity of the lactyl ether synthesis step from racemic 2-chloropropionic acid. Similarly, syntheses employing pure enantiomers of 2-chloropropionic acid were disclosed as not completely stereospecific. Coupling products with L- and D-alanine esters were prepared for

  一种改进的，大规模制备描述，由2-乙酰氨基-2-脱氧- d-葡萄糖导致苄基2-乙酰氨基-4,6- ø -亚苄基-3- ö - [（R）-1-羧乙基] -2-脱氧α-d-D-吡喃葡萄糖苷（α-苄ñ -乙酰基-4,6- ö -benzylidenemuramic酸。5R）和它的（小号） -异构体（α-苄ñ -乙酰基-4,6- ø -亚苄基isomuramic酸，5S）通过它们的甲酯（色谱分离4R和4S）。4r和4s的高产量和完全分离可以可靠地评估由外消旋2-氯丙酸合成的乳酸醚合成步骤的立体选择性低。类似地，公开了使用2-氯丙酸的纯对映异构体的合成不是完全立体特异性的。制备了5r和5s的具有L-和D-丙氨酸酯的偶联产物。
• A Facile Synthesis of Benzyl 2-Amino-3-azido-4-<i>O-p</i>-methoxybenzyl-6-<i>O</i>-benzyl-2,3-dideoxy-α-<scp>d</scp>-glucopyranoside: A Key Intermediate in the Formation Of A Didemnin B Analog
  作者：Joshi M. Ramanjulu、Madeleine M. Joullié

  DOI：10.1080/07328309608005660

  日期：1996.4

  Although the deprotection of amides by hydrazinolysis is a well established method in carbohydrate chemistry, this reaction is dependent upon the nearby substituents. In our facile synthesis of intermediate benzyl 2-amino-3-azido-4-O-p-methoxybenzyl-6-O-benzyl-2,3-dideoxy-α-d-glucopyranoside (3), we found that the use of trifluoroacetamides provided a more efficient protection strategy.

  尽管通过肼解作用使酰胺脱保护是碳水化合物化学中公认的方法，但该反应取决于附近的取代基。在我们轻松合成中间体苄基2-氨基-3-叠氮基-4- Op-甲氧基苄基-6- O-苄基-2,3-二脱氧-α- d-吡喃葡萄糖苷（3）时，我们发现使用了三氟乙酰胺更有效的保护策略。
• Novel immunological adjuvant compounds and methods of preparation thereof
  申请人：Syntex (U.S.A.) Inc.

  公开号：US04082735A1

  公开（公告）日：1978-04-04

  This application relates to novel immunological adjuvant compounds of the formula: ##STR1## wherein each of R and R.sup.1 are the same or different and are hydrogen or an acyl radical; R.sup.2 is an unsubstituted or substituted alkyl radical, or an unsubstituted or substituted aryl radical; X is an aminoacyl moiety; and Y is D-isoasparagine or D-isoglutamine.

  该应用涉及一种新型免疫佐剂化合物，其化学式为：##STR1## 其中R和R.sup.1分别相同或不同，为氢或酰基基团；R.sup.2为未取代或取代的烷基基团，或未取代或取代的芳基基团；X为氨基酰基基团；Y为D-异天冬酰胺或D-异谷氨酰胺。
• Novel carbohydrate-derived pyridinecarboxylic organocatalysts for the enantioselective reduction of imines with trichlorosilane
  作者：Xin Ge、Chao Qian、Yunbin Chen、Xinzhi Chen

  DOI：10.1016/j.tetasy.2014.03.015

  日期：2014.4

  A new type of carbohydrate-derived pyridinecarboxylic organocatalyst was prepared by fine-tuning a D-glucosamine backbone at the C-2 and C-3 positions. The carbohydrate-derived pyridinecarboxylic organocatalyst was used for the enantioselective reduction of imines with trichlorosilane. The reduction proceeded in high yield (up to 93%) and with moderate enantioselectivity (up to 75%). (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of novel carbohydrate-based chiral P, N ligands and their applications in Cu-catalyzed enantioselective 1, 4-conjugate additions
  作者：Haijun Xia、Hua Yan、Chao Shen、Fangyi Shen、Pengfei Zhang

  DOI：10.1016/j.catcom.2011.09.021

  日期：2011.11

  A new type of phosphate-pyridine (P, N) ligand derived from D-glucosamine and BINOL was synthesized and successfully applied in Cu-catalyzed enantioselective conjugate addition of diethylzinc to chalcones for the first time, high yields and enantioselectivities were obtained when the ligand 10a which contains (S)-BINOL was used. The results also showed that the configuration of BINOL at the ligand backbone had remarkable effects on the activities and enantioselectivities. (C) 2011 Elsevier B.V. All rights reserved.