methyl 2,6-bis-O-benzoyl-α-D-galactopyranoside | 26927-44-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,6-bis-O-benzoyl-α-D-galactopyranoside
• 英文别名: methyl 2,6-di-O-benzoyl-α-D-galactopyranoside；Methyl-2,6-di-O-benzoyl-α-D-galactopyranosid；[(2R,3R,4S,5R,6S)-5-benzoyloxy-3,4-dihydroxy-6-methoxyoxan-2-yl]methyl benzoate
• CAS: 26927-44-6；29575-26-6；51996-13-5；88087-63-2；29575-27-7
• 化学式: C₂₁H₂₂O₈
• 分子量: 402.401
• InChiKey: XILYXPMGDAVPPF-GFZGVUQPSA-N

物化性质

• 熔点：
  141-142 °C
• 沸点：
  568.8±50.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2,6-bis-O-benzoyl-α-D-galactopyranoside 在 吡啶 、 硫酸 、 D(+)-10-樟脑磺酸 、 溶剂黄146 作用下， 以 苯 为溶剂， 反应 49.0h， 生成 1,3-di-O-acetyl-2,4,6-tri-O-benzoyl-α-D-galactopyranose
  参考文献：
  名称：

  Study of glycosylation with N-trichloroacetyl-d-glucosamine derivatives in the syntheses of the spacer-armed pentasaccharides sialyl lacto-N-neotetraose and sialyl lacto-N-tetraose, their fragments, and analogues

  摘要：

  The syntheses of 2-aminoethyl glycosides of the pentasaccharides Neu5Ac-alpha (2 --> 3)-Gal-beta (3(1 --> 4)-GlcNAc-beta (3(1 --> 3)-Gal-beta (1 --> 4)-Glc and Neu5Ac-alpha (2 --> 3)-Gal-beta (1 --> 3)-GlcNAc-beta (1 --> 3)-Gal-beta (1 --> 4)-Glc, their asialo di-, tri-, and tetrasaccharide fragments, and analogues included a systematic study of glycosylation with variously protected mono- and disaccharide donors derived from N-trichloroacetyl-D-glucosamine of galactose, lactose, and lactosamine glycosyl acceptors bearing benzoyl protection around the OH group to be glycosylated. Despite the. low reactivity of these acceptors, stereo specificity and good to excellent yields were obtained with NIS-TfOH-activated thioglycoside donors of such type, or with AgOTf-activated glycosyl bromides, while other promotors, as well as a trichloroacetimidate donor, were less effective, and a beta -acetate donor was inactive. In NIS-TfOH-promoted glycosylation with the thioglycosides, the use of TfOH in catalytic amount led to rapid formation of the corresponding oxazoline, but the quantity of TfOH necessary for further efficient coupling with an acceptor depended on the reactivity of the donor, varying from 0.07 equiv for a 3,6-di-O-benzylated monosaccharide derivative to 2.1 equiv for a peracetylated disaccharide one. In the glycosylation products, the N-trichloroacetyl group was easily converted into N-acetyl by alkaline hydrolysis followed by N-acetylation. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(01)00213-0
• 作为产物：
  描述：

  methyl 3,4-O-isopropylidene-α-D-galactopyranoside 在 吡啶 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 methyl 2,6-bis-O-benzoyl-α-D-galactopyranoside
  参考文献：
  名称：

  半乳糖受体糖基化反应的区域选择性：实验和理论研究。

  摘要：

  区域选择性糖基化允许为寡糖的合成规划更简单的策略，从而减少了使用保护基的需要。为了进一步了解这种区域选择性，我们分析了糖基化反应中2，6-二保护的甲基α-和β-吡喃半乳糖苷衍生物的OH-3和OH-4基团的相对反应性。通过简单的方法有效地制备了糖基受体，并评估了具有不同反应性的糖基供体。由于OH-3基团的赤道取向，实现了对1→3产物的高区域选择性。分子建模方法支持了支持O-3取代的总体趋势，尽管它显示出一些无法解释控制某些受体之间区域选择性差异的微妙因素的能力。然而，可以通过使用本文测定的一些受体在区域上选择性地安装Galp-（β1→3）-Galp连接。

  DOI：

  10.3762/bjoc.15.294

文献信息

• Boronic esters as protective groups in carbohydrate chemistry: processes for acylation, silylation and alkylation of glycoside-derived boronates
  作者：Ross S. Mancini、Jessica B. Lee、Mark S. Taylor

  DOI：10.1039/c6ob02278b

  日期：——

  Procedures for selective installation of acyl, silyl ether and para-methoxybenzyl (PMB) ether groups to glycoside substrates have been developed, employing phenylboronic esters as protected intermediates. The sequence of boronic ester formation, functionalization and deprotection can be accomplished with only a single purification step, and the boronic acid component can be recovered and reused after

  选择性安装酰基，甲硅烷基醚和对位的程序已经开发了使用苯基硼酸酯作为受保护的中间体的对糖苷底物的-甲氧基苄基（PMB）醚基。硼酸酯形成，官能化和脱保护的顺序仅需一个纯化步骤即可完成，脱硼后可回收并再利用硼酸组分。关键的进展包括确定在硼酸酯存在下安装PMB基团的反应条件，以及霍尔和同事开发的“相转换”规程作为硼酸酯裂解的有效方法的使用。硼酸酯脱保护的相对温和的条件可耐受几个官能团，包括酯，甲硅烷基醚，缩酮和硫代糖苷。
• <i>N</i> ‐Acetyl‐5‐ <i>N</i> ,4‐ <i>O</i> ‐oxazolidinone‐Protected Sialyl Sulfoxide: An α‐Selective Sialyl Donor with Tf ₂ O/(Tol) ₂ SO in Dichloromethane
  作者：Zhen‐yuan Gu、Jia‐xin Zhang、Guo‐wen Xing

  DOI：10.1002/asia.201200172

  日期：2012.7

  Sweet as sugar: Sialyl sulfoxide protected by N‐acetyl‐5‐N,4‐O‐oxazolidinone was readily prepared, and its coupling to various sugar acceptors was investigated. When the reaction was promoted by Tf2O/(Tol)2SO, efficient and highly α‐selective sialylation yielded α(2,6), α(2,3), and α(2,4) glycosidic linkages between sialic acid and glucose/glacotose.

  像糖一样甜：很容易制备受N-乙酰基-5- N，4 - O-恶唑烷酮保护的唾液酸亚砜，并研究了它与各种糖受体的偶联作用。当Tf 2 O /（Tol）2 SO促进反应时，有效且高度α-选择性的唾液酸化会产生唾液酸之间的α（2,6），α（2,3）和α（2,4）糖苷键和葡萄糖/半乳糖。
• Diastereoselective formation of pyruvylated glycosides from partly protected sugars and methyl pyruvate
  作者：Thomas Ziegler、Elisabeth Eckhardt、Gerhard Herold

  DOI：10.1016/s0040-4039(00)60097-7

  日期：1992.7

  Various partly protected sugars (gluco-, manno-, and galactopyranosides) were acetalized with methyl pyruvate in moderate to good yield with BF3-etherate as the condensing reagent. Thus, (1-methoxycarbonyl)ethylidene glycosides were obtained diastereoselectivity.

  各种部分受保护的糖（葡萄糖基，甘露糖苷和半乳糖吡喃糖苷）以丙酮酸甲酯缩醛化，并以BF 3-醚酸酯为缩合试剂。因此，获得了（1-甲氧基羰基）亚乙基糖苷的非对映选择性。
• Tsuda, Yoshisuke; Haque, Md. Ekramul; Yoshimoto, Kimihiro, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 5, p. 1612 - 1624
  作者：Tsuda, Yoshisuke、Haque, Md. Ekramul、Yoshimoto, Kimihiro

  DOI：——

  日期：——
• Regioselective stannylation
  作者：Tomoya Ogawa、Masanao Matsui

  DOI：10.1016/s0040-4020(01)88890-6

  日期：1981.1