methyl 2,3,6-tri-O-benzyl-4-O-(2',3',6'-tri-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside | 19474-56-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,6-tri-O-benzyl-4-O-(2',3',6'-tri-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside
• 英文别名: methyl 2,3,6-tri-O-benzyl-4-O-(2,3,6-tri-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside；methyl 2,3,6,2',3',6'-hexa-O-benzyl-β-lactoside；methyl 2,3,6,2',3'6'-hexa-O-benzyl-β-lactoside；Bn(-2)[Bn(-3)][Bn(-6)]Gal(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]b-Glc1Me；(2R,3S,4S,5R,6S)-6-[(2R,3R,4S,5R,6R)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-ol
• CAS: 19474-56-7；19474-57-8；127243-56-5；92733-60-3
• 化学式: C₅₅H₆₀O₁₁
• 分子量: 897.075
• InChiKey: AOHOBOWOJXBEMI-RBSKJUBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  66
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 2,3,6-tri-O-benzyl-4-O-(2',3',6'-tri-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 2.75h， 以60%的产率得到methyl 2,3,6,2',3',6'-hexa-O-benzyl-4'-deoxy-4'-fluoro-β-cellubioside
  参考文献：
  名称：

  合成所有可能的单甲基醚和甲基β-乳糖苷的几种脱氧卤代类似物，作为蓖麻蓖麻凝集素的配体。

  摘要：

  甲基β-内酯（1）的所有可能的单甲基醚的合成已从1直接进行，利用了烷基化和甲锡烷基化反应中羟基的不同反应性。另外，通过适当的底物与二乙基氨基三氟化硫或氟化四丁基铵的反应制备了在6,3'，4'，epi-4'和6'位置的1的脱氧氟衍生物。最后，还制备了1的6-脱氧碘和6'-溴脱氧氧基类似物。

  DOI：

  10.1016/0008-6215(94)84243-4
• 作为产物：
  描述：

  苯甲醛二甲缩醛 在 盐酸 、 3 A molecular sieve 、 sodium cyanoborohydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 1.0h， 生成 methyl 2,3,6-tri-O-benzyl-4-O-(2',3',6'-tri-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  对应于肺炎链球菌识别的受体结构的二糖，三糖和四糖的合成

  摘要：

  摘要描述了甲基2-乙酰氨基-2-脱氧-4-O-β-d-吡喃半乳糖苷-α-d-吡喃葡萄糖苷，甲基2-乙酰氨基-2-脱氧-4- O-β-d-吡喃半乳糖苷-β的合成-d-吡喃葡萄糖苷，甲基3- O-（2-乙酰氨基-2-脱氧-β-d-吡喃葡萄糖基-β-d-吡喃半乳糖苷，甲基3- O-（2-乙酰氨基-2-脱氧-4- O-β -d-吡喃半乳糖基-β-d-吡喃吡喃糖基）-β-d-吡喃半乳糖苷和甲基4-O-[3-O-（2-乙酰氨基-2-脱氧-4-O-β-d-吡喃半乳糖基-β- d-吡喃葡萄糖基）-β-d-吡喃半乳糖基]-β-d-吡喃葡糖苷。

  DOI：

  10.1016/0008-6215(85)85219-8

文献信息

• Synthesis and hydrolysis studies of novel glyco-functionalized platinum complexes
  作者：Janina Möker、Joachim Thiem

  DOI：10.1016/j.carres.2011.08.024

  日期：2012.2

  and some of its derivatives are among the most active cytostatics for cancer treatment. Unfortunately, application of platinum complexes always indicates side effects, and frequently primary or developed resistance of tumour cells appear. Therefore, development of novel analogues especially with natural ligands is expedited. Glyco-functionalized ligands were obtained via ether synthesis with omega-halo

  顺铂及其某些衍生物是治疗癌症最活跃的细胞抑制剂。不幸的是，铂络合物的施用总是表明副作用，并且经常出现肿瘤细胞的原发性或发达抗性。因此，加快了特别是天然配体的新型类似物的开发。通过与ω-卤代醚的醚合成，Finkelstein反应，丙二酸酯的进一步处理和最终的脱保护，然后制备二钠盐，来获得糖基官能化的配体。随后的络合产生了新的铂衍生物，研究了其在水溶液介质中的稳定性。
• Studies of the molecular recognition of synthetic methyl β-lactoside analogues by Ricinus communis agglutinin
  作者：Alfonso Rivera-Sagredo、Jesús Jiménez-Barbero、Manuel Martín-Lomas、Dolores Solís、Teresa Díaz-Mauriño

  DOI：10.1016/0008-6215(92)80055-6

  日期：1992.8

  The 2-, 3-, 6-, 2'-, 3'-, 4'-, and 6'-deoxy derivatives and the 3-O-methyl derivative of methyl beta-lactoside have been synthesised and their binding to the galactose-specific agglutinin from Ricinus communis (RCA-120) has been investigated. The results indicate that HO-3,4,6 of the beta-D-galactopyranose moiety are the key polar groups. The main difference from the closely related ricin lectin RCA-60

  已经合成了甲基β-乳糖苷的2-，3-，6-，2'-，3'-，4'-和6'-脱氧衍生物和3-O-甲基衍生物，并且它们与半乳糖结合研究了来自蓖麻的特异性凝集素（RCA-120）。结果表明，β-D-吡喃半乳糖部分的HO-3、4、6是关键的极性基团。与紧密相关的蓖麻毒素凝集素RCA-60的主要区别在于D-吡喃葡萄糖部分的HO-6，这似乎有助于碳水化合物与RCA-60的结合而不与RCA-120的结合。
• Synthesis of the trisaccharide moiety of gangliotriosylceramide (asialo GM2)
  作者：Hans-Peter Wessel、Tommy Iversen、David R. Bundle

  DOI：10.1016/0008-6215(84)85266-0

  日期：1984.7

  The synthesis of the trisaccharide methyl glycoside beta-D-GalNAc-(1----4)-beta-D-Gal-(1----4)-beta-D-Glc-OMe, which corresponds to the carbohydrate portion of gangliotriosylceramide (asialo GM2), was accomplished by the reaction of 4-O-acetyl-3,6-di-O-benzoyl-2-deoxy-2-phthalimido-D-galactopyranosyl bromide (18) with a benzylated derivative of methyl 4-O-beta-D-galactopyranosyl-beta-D-glucopyranoside

  三糖甲基糖苷β-D-GalNAc-（1 ---- 4）-β-D-Gal-（1 ---- 4）-β-D-Glc-OMe的合成部分神经节三糖基神经酰胺（亚氨基GM2）是通过使4-O-乙酰基-3,6-二-O-苯甲酰基-2-脱氧-2-邻苯二甲酰亚胺基-D-吡喃半乳糖苷溴化物（18）与甲基4-O-β-D-吡喃半乳糖基-β-D-吡喃葡萄糖苷。用6'-苄基醚和6'-苯甲酸酯进行的比较研究表明，O-6'处的取代基对于O-4'处糖基化的结果至关重要，醚衍生物的反应性更高。从葡糖衍生物通过单次获得叔丁基4-O-乙酰基-3,6-二-O-苯甲酰基-2-脱氧-2-邻苯二甲酰亚胺基-D-吡喃半乳糖苷，其易于转化为相应的溴化物18。 -步，
• An efficient glycosylation reaction for the synthesis of asialo GM2 analogues
  作者：Bin Sun、Aliaksei V. Pukin、Gerben M. Visser、Han Zuilhof

  DOI：10.1016/j.tetlet.2006.08.008

  日期：2006.10

  We investigated the coupling reaction of glycosyl donors N-trichloroethoxycarbonyl-galactosamine-O-trichloroacetimidate (2a) and N-p-nitrobenzyloxycarbonyl-galactosamine-O-trichloroacetimidate (2b) with the 4'-OH of lactose derivatives (3a-d) to synthesize key intermediates of asialo GM2 analogues, and found that the glycosylation yield with 2a was 90% or more in all investigated cases. (c) 2006 Elsevier Ltd. All rights reserved.
• Inhibition of Cellobiohydrolases fromTrichoderma reesei. Synthesis and Evaluation of Some Glucose-, Cellobiose-, and Cellotriose-Derived Hydroximolactams andImidazoles
  作者：Stefan Vonhoff、Kathleen Piens、Muriel Pipelier、Christophe Braet、Marc Claeyssens、Andrea Vasella

  DOI：10.1002/(sici)1522-2675(19990707)82:7<963::aid-hlca963>3.0.co;2-v

  日期：1999.7.7

  The lactam 16, the hydroximolactams 8, 20, 23, and 27, and the imidazole 32 were prepared following known methods. They were tested together with the known tetrazole 35 and the hydroximolactams 2 and 36 as inhibitors of the cellobiohydrolases Cel7A and Cel6A from Trichoderma reesei. Cel7A is only weakly inhibited by these compounds. Comparing their inhibitory activity evidences the importance of occupying subsites tl and +2. We results strongly suggest that the shape of none of the variants of the lactone-type inhibitor motif embodied by these inhibitors is complementary to the subsite - 1, i.e.,analogous to the transition state. Cel6A is rather strongly inhibited by the cellobiose analogues 20, 23, and 32, and by the cellotriose analogue 27. Their relative inhibitory activities evidence that binding at subsite -2 depends upon the shape of the moiety occupying subsite - 1. There is only a small difference between the inhibition by the hydroximolactams 20 and 23, which may be (partially) protonated by the catalytic acid of either anti- or syn-protonating glycosidases, and the imidazole 32, which can only be protonated by anti-protonating glycosidases. The results strongly suggest that shape requirements must be met by glycosidase inhibitors before they can be used to characterize the proton trajectory of glycosidases.