methyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside | 92733-57-8

• 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-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside
• 英文别名: methyl 2,2',3,3',6-penta-O-benzyl-β-lactoside；methyl 2,3,6,2',3'-penta-O-benzyl-β-lactoside；Bn(-2)[Bn(-3)]Gal(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]b-Glc1Me；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(2R,3R,4S,5R,6R)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 92733-57-8
• 化学式: C₄₈H₅₄O₁₁
• 分子量: 806.95
• InChiKey: WLXVZBVZRGOIOW-UFXDQSFSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  59
• 可旋转键数：
  20
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  124
• 氢给体数：
  2
• 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-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside 在 palladium on activated charcoal 二乙胺基三氟化硫 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.58h， 生成 Methyl 6'-deoxy-6'-fluoro β-lactoside
  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：

  甲基 4-O-BETA-D-半乳糖基-BETA-D-吡喃葡萄糖苷 在 sodium hydride 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 methyl 2,3,6-tri-O-benzyl-4-O-(2,3-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Carbohydrate-derived surfactants: synthesis and phase behaviour of methyl 4′ 6′-di-O-alkyl-β-lactosides

  摘要：

  In order to study the physical properties of lactose-derived surfactants. methyl 4',6'-di-O-hexyl-beta-lactoside and methyl 4',6'-di-O-octyl-beta-lactoside were prepared. The 4',6'-O-isopropylidene ketal was used as a temporary protecting group in the key intermediate. The 3',4'-O-benzylidene acetal was identified as a minor by-product in the preparation of methyl 4',6'-O-benzylidene-beta-lactoside by acid-catalysed transacetalation. The phase behaviour of these derivatives is reported.

  DOI：

  10.1039/p19940002103

文献信息

• 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，
• Syntheses of all the possible monomethyl ethers and several deoxyhalo analogues of methyl β-lactoside as ligands for the Ricinus communis lectins
  作者：Paloma Fernández、Jesús Jiménez-Berbero、Manuel Martín-Lomas

  DOI：10.1016/0008-6215(94)84243-4

  日期：1994.2

  The synthesis of all the possible monomethyl ethers of methyl beta-lactoside (1) has been performed from 1 in a straightforward way, making use of the different reactivity of the hydroxyl groups in alkylation and stannylation reactions. In addition, the deoxyfluoro derivatives of 1 at positions, 6,3',4',epi-4', and 6' have been prepared by reaction of the appropriate substrates with diethylaminosulfur

  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。
• Carbohydrate-derived surfactants: synthesis and phase behaviour of methyl 4′ 6′-di-O-alkyl-β-lactosides
  作者：Virginie Langlois、J. Michael Williams

  DOI：10.1039/p19940002103

  日期：——

  In order to study the physical properties of lactose-derived surfactants. methyl 4',6'-di-O-hexyl-beta-lactoside and methyl 4',6'-di-O-octyl-beta-lactoside were prepared. The 4',6'-O-isopropylidene ketal was used as a temporary protecting group in the key intermediate. The 3',4'-O-benzylidene acetal was identified as a minor by-product in the preparation of methyl 4',6'-O-benzylidene-beta-lactoside by acid-catalysed transacetalation. The phase behaviour of these derivatives is reported.