methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside | 6748-91-0

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside
• 英文别名: Methyl 4,6-O-Benzylidene-2,3-di-O-benzoyl-α-D-glucopyranoside；Methyl 2,3-Di-O-benzoyl-4,6-O-benzylidene-alpha-D-glucopyranoside；[(4aR,6S,7R,8S,8aR)-7-benzoyloxy-6-methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] benzoate
• CAS: 6748-91-0
• 化学式: C₂₈H₂₆O₈
• 分子量: 490.51
• InChiKey: CGMUHSNJRXPSSA-IHTZYYJZSA-N

物化性质

• 熔点：
  152.0 to 157.0 °C

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

安全信息

• 海关编码：
  29389090

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 在 盐酸 、 sodium cyanoborohydride 作用下， 生成 methyl 6-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of p-nitrophenyl 65-O-benzyl-α-maltopentaoside, a substrate for alpha amylases

  摘要：

  p-Nitrophenyl alpha-maltopentaoside, having a benzyl group on O-6 of the terminal (nonreducing) D-glucosyl group was prepared by use of a reductive ring-opening reaction. Highly regioselective reduction of p-nitrophenyl O-(2,3-di-O-benzoyl-4,6-O-benzylidene-alpha-D-glucopyranosyl)-(1----4)- tris[O-(2,3,6-tri-O-benzoyl-alpha-D-glucopyranosyl)-(1----4)]-2,3,6-tri- O- benzoyl-alpha-D-glucopyranoside by dimethylamine-borane and p-toluenesulfonic acid, followed by debenzoylation, gave p-nitrophenyl O-(6-O-benzyl-alpha-D-glucopyranosyl)-(1----4)-tris[O-alpha-D-glucopyran osyl- (1----4)]-alpha-D-glucopyranoside. An experiment was done on the mode of action of human pancreatic and salivary alpha amylases on this derivative. The compound is suitable as a substrate for the assay of alpha amylase when used with glucoamylase and alpha-D-glucosidase as coupling enzymes.

  DOI：

  10.1016/0008-6215(88)84062-x
• 作为产物：
  描述：

  alpha-甲基葡萄糖甙 在 吡啶 、 zinc(II) chloride 作用下， 反应 0.67h， 生成 methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside
  参考文献：
  名称：

  Chittenden, Gordon J. F., Recueil des Travaux Chimiques des Pays-Bas, 1988, vol. 107, p. 607 - 609

  摘要：

  DOI：

文献信息

• Oligosaccharide glycosides having mammalian immunosuppresive and
  申请人：Glycomed Incorporated

  公开号：US05874411A1

  公开（公告）日：1999-02-23

  Disclosed are novel oligosaccharide glycosides having mammalian immunosuppressive and tolerogenic properties, pharmaceutical compositions containing such oligosaccharide glycosides and to methods of using such oligosaccharide glycosides to modulate cell-mediated immune responses in a mammal.

  揭示了具有哺乳动物免疫抑制和耐受性特性的新型寡糖糖苷，包含这种寡糖糖苷的药物组合物以及使用这种寡糖糖苷调节哺乳动物细胞介导免疫应答的方法。
• Regioselective O-deacylation of fully acylated glycosides and 1,2-O-isopropylidenealdofuranose derivatives with hydrazine hydrate
  作者：Hoshiharu Ishido、Nobuo Sakairi、Masao Sekiya、Nobuo Nakazaki

  DOI：10.1016/s0008-6215(00)80525-x

  日期：1981.11

  partial O -deacylation of fully acylated methyl glycosides and some other glycosyl compounds (23 compounds) was found to be induced, to give, in good yields, products bearing one free hydroxyl group; the results obtained indicated that, among the primary and secondary O -acyl groups, the 2- O -acyl groups were, in general, the most labile toward the nucleophile (hydrazine). Hydrazinolysis of 1,2- O -

  摘要在1：4乙酸-吡啶中进行肼解后，在吡啶中，可诱导完全酰化的甲基糖苷和某些其他糖基化合物（23种化合物）的部分O-脱酰作用，从而以较高的收率得到含1种化合物的产物。游离羟基 所得结果表明，在伯和仲O-酰基中，2-O-酰基通常对亲核试剂（肼）最不稳定。另一方面，对1，2-O-异亚丙基戊二醛呋喃糖酰化物（3种化合物）进行水合肼解，以高收率得到相应的在其伯羟基上具有保护基的单酰基衍生物。讨论了可能与肼解的区域选择性有关的因素。
• Reactions of relevance to the chemistry of aminoglycoside antibiotics. Part 13. A novel synthesis of benzyl ethers
  作者：Anthony G. M. Barrett、Roger W. Read、Derek H. R. Barton

  DOI：10.1039/p19800002184

  日期：——

  Benzyl ethers were prepared from alcohols by reaction with chloro(phenylmethylene)dimethylammonium chloride and sodium hydrogen telluride in sequence. The salt (1)[Me2NC(R1)OR2Cl–; R1= H, R2= cholest-5-en-3β-yl] and sodium borohydride gave the borane complex of 3β-dimethylaminomethoxycholest-5-ene. Salt (1; R1= Ph, R2= cholest-5-en-3β-yl or 5α-cholestan-3β-yl) and ammonia or hydrazine gave the steroidal

  通过依次与氯（苯基亚甲基）二甲基氯化铵和碲化氢钠反应，由醇制得苄基醚。盐（1）[我2 NC（R 1）OR 2氯- ; R 1＝ H，R 2＝胆甾-5-烯-3β-基]，硼氢化钠得到3β-二甲基氨基甲氧基胆甾-5-烯的硼烷配合物。盐（1； R 1 = Ph，R 2 =胆甾-5-en-3β-基或5α-胆甾-3β-基）和氨或肼得到甾族苯甲酸酯或苯甲酰肼酸盐。
• Site-Selective Acylations with Tailor-Made Catalysts
  作者：Florian Huber、Stefan F. Kirsch

  DOI：10.1002/chem.201600790

  日期：2016.4.18

  The acylation of alcohols catalyzed by N,N‐dimethylamino pyridine (DMAP) is, despite its widespread use, sometimes confronted with substrate‐specific problems: For example, target compounds with multiple hydroxy groups may show insufficient selectivity for one hydroxyl, and the resulting product mixtures are hardly separable. Here we describe a concept that aims at tailor‐made catalysts for the site‐specific

  N，N催化醇的酰化反应二甲氨基吡啶（DMAP）尽管已被广泛使用，但有时仍会遇到特定于底物的问题：例如，具有多个羟基的目标化合物可能对一个羟基的选择性不足，并且所得产物混合物几乎不可分离。在这里，我们描述了一种旨在针对特定位点的酰化量身定制催化剂的概念。为此，我们介绍了一个催化剂库，其中的每个条目都是通过将可变且易于调节的肽支架与基于DMAP的催化活性单元相连接而构建的。对于选定的例子，我们演示了库筛选如何导致优化催化剂的鉴定，并且与仅DMAP相比，目标底物可以显着提高的位点选择性转化。此外，
• Three Solvent-Free Catalytic Approaches to the Acetal Functionalization of Carbohydrates and Their Applicability to One-Pot Generation of Orthogonally Protected Building Blocks
  作者：Serena Traboni、Emiliano Bedini、Maddalena Giordano、Alfonso Iadonisi

  DOI：10.1002/adsc.201500745

  日期：2015.11.16

  alternative protocols were developed to carry out the selective installation of acetal groups on carbohydrates and polyols under mildly acidic, solvent-free conditions. One protocol is based on a diol/aldehyde condensation at room temperature, with an acetolysis process serving for the activation of the carbonyl component. A second approach is based on an orthoester-mediated activation of the carbonyl component

  开发了三种替代方案，以在弱酸性，无溶剂的条件下选择性地将缩醛基团安装在碳水化合物和多元醇上。一种方案是基于在室温下的二醇/醛缩合，其中乙酰解过程用于活化羰基组分。第二种方法是基于在高温下原酸酯介导的羰基组分的活化。第三方案相反是要求一种转缩醛化机制。这些方法的结合使得可以在非常简单的实验条件下，在空气中短时间内访问各种缩醛保护的构建基块。