β-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose | 51885-41-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• 英文别名: 6-O-β-D-galactopyranosyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose；(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxane-3,4,5-triol
• CAS: 51885-41-7
• 化学式: C₁₈H₃₀O₁₁
• 分子量: 422.43
• InChiKey: INRMYZZMSZQZFR-LANDYSMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  β-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 sodium hydride 、 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-O-benzyl-3,4-O-isopropylidene-6-O-(methoxydimethyl)methyl-β-D-galactopyranosyl-(1-> 6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Scope and limitation of the application of the (methoxydimethyl)methyl group in the synthesis of 2′-O-, 6′-O- and 2′,6′-di-O-(α-l-arabinofuranosyl)-β-d-galactopyranosyl-(1→6)-d-galactoses

  摘要：

  For the characterisation of the anticipated epitope of an arabinogalactan, isolated from the extract of Echinacea purpurea, the trisaccharide alpha-L-Araf-(1 --> 2)-beta-D-Galp-(1 --> 6)-D-Gal was synthesized. The easily available 3,4-O-isopropylidene-6-O-(methoxydimethyl)methyl-beta-D-galactopyranosyl- (1 --> 6)-1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose having the OH-2' free served as aglycone upon direct arabinosylation at the 2' position under Helferich conditions. The formed HgBr2 cleaved the acid sensitive protecting group at position 6', but under basic conditions the desired, fully protected trisaccharide, or its symmetrical dimerization derivative linked 6'- to 6'-position via an isopropylidene bridge, could be obtained. An alternative route involved arabinosylation of a hepta-O-acetylated digalactose with free OH-2'. Two other oligosaccharides, namely, alpha-L-Araf-(1 --> 6)-beta-D-Galp-(1 --> 6)-D-Gal and (alpha-L-Araf)(2)-(1 --> 2,6)-beta-D-Galp-(1 --> 6)-D-Gal were also synthesized and characterised. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(99)00094-4
• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 24.0h， 生成 β-D-galactopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  3- O-芳基甲磺酸化（1→6）-β-D-加拉普坦表位的合成

  摘要：

  两个四聚阿拉伯半乳聚糖，β- D-吡喃半乳糖-（1→6）-β- D-吡喃半乳糖-（1→6）-[α- L-阿拉伯呋喃糖基- （1→3）]- D-吡喃半乳糖（14）和α -L-阿拉伯呋喃糖基- （1→3）-β- D-吡喃半乳糖基-（1→6）-β- D-吡喃半乳糖基-（1→6）-D-吡喃半乳糖（25），它们是CCRC-M7的良好候选者抗原表位表征，使用收敛策略进行了有效合成。受体乙酰基的迁移被证明是合成的障碍，但是区域选择性糖基化或4- O受体的-苄基保护避免了这个问题，从而可以有效合成1→6连接的目标化合物。

  DOI：

  10.1081/car-100104865

文献信息

• A convenient new pathway for stereospecific epimerization of monosaccharide moieties in disaccharides
  作者：Ralf Miethchen、Daniel Rentsch、Michael Frank、András Lipták

  DOI：10.1016/0008-6215(95)00338-x

  日期：1996.2

  yl-1-thio-beta-D-glucopyranoside (7) were selectively acetalated with chloral-dicyclohexylcarbodiimide in a nonclassical pathway. During acetalation, the D-mannopyranosyl moiety of the disaccharide 2 and the unprotected beta-D-galactopyranosyl moieties of 4 and 7 were epimerized at their 3-positions, generating D-altro- and D-gulo-pyranosyl moieties, respectively.

  二糖苄基4,6-O-亚苄基-2-O-α-D-甘露吡喃糖基-β-D-吡喃葡萄糖苷（2），6-O-β-D-吡喃并吡喃糖基-1,2：3,4-二- O-异亚丙基-α-D-吡喃半乳糖（4）和苯基4-O-β-D-吡喃半乳糖基-1-硫代-β-D-吡喃葡萄糖苷（7）用氯代二环己基碳二亚胺选择性地乙缩醛化。在缩醛化过程中，二糖2的D-甘露吡喃糖基部分和4和7的未保护的β-D-吡喃半乳糖基部分在其3位上差向异构，分别生成D-altro和D-gulo-吡喃糖基部分。
• Glycosylation Using Unprotected Alkynyl Donors
  作者：Sreeman K. Mamidyala、M.G. Finn

  DOI：10.1021/jo901857x

  日期：2009.11.6

  Gold(III) activation of unprotected propargyl glycosyl donors has been shown to be effective for the synthesis of saccharides. Terminal propargyl glycosides of glucose, galactose, and mannose required heating at reflux in acetonitrile with 5% AuCl(3) for reaction with various primary alcohol acceptors, the latter used in 10-fold molar excess relative to donor. Donors containing the 2-butynyl group were more reactive, giving good yields of glycoside products at lower temperatures Secondary alcohols could also be used but with diminished efficiency. The propargylic family of donors is especially convenient because they can be easily prepared on large scale by Fischer glycosylation and stored indefinitely before chemoselective activation by the catalyst.
• Can Side-Chain Conformation and Glycosylation Selectivity of Hexopyranosyl Donors Be Controlled with a Dummy Ligand?
  作者：Kapil Upadhyaya、Nicolas Osorio-Morales、David Crich

  DOI：10.1021/acs.joc.2c02889

  日期：2023.3.17
• Scope and limitation of the application of the (methoxydimethyl)methyl group in the synthesis of 2′-O-, 6′-O- and 2′,6′-di-O-(α-l-arabinofuranosyl)-β-d-galactopyranosyl-(1→6)-d-galactoses
  作者：Anikó Borbás、Lóránt Jánossy、András Lipták

  DOI：10.1016/s0008-6215(99)00094-4

  日期：1999.5

  For the characterisation of the anticipated epitope of an arabinogalactan, isolated from the extract of Echinacea purpurea, the trisaccharide alpha-L-Araf-(1 --> 2)-beta-D-Galp-(1 --> 6)-D-Gal was synthesized. The easily available 3,4-O-isopropylidene-6-O-(methoxydimethyl)methyl-beta-D-galactopyranosyl- (1 --> 6)-1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose having the OH-2' free served as aglycone upon direct arabinosylation at the 2' position under Helferich conditions. The formed HgBr2 cleaved the acid sensitive protecting group at position 6', but under basic conditions the desired, fully protected trisaccharide, or its symmetrical dimerization derivative linked 6'- to 6'-position via an isopropylidene bridge, could be obtained. An alternative route involved arabinosylation of a hepta-O-acetylated digalactose with free OH-2'. Two other oligosaccharides, namely, alpha-L-Araf-(1 --> 6)-beta-D-Galp-(1 --> 6)-D-Gal and (alpha-L-Araf)(2)-(1 --> 2,6)-beta-D-Galp-(1 --> 6)-D-Gal were also synthesized and characterised. (C) 1999 Elsevier Science Ltd. All rights reserved.
• SYNTHESIS OF 3-<i>O</i>-ARABINOSYLATED (1→6)-β-<scp>D</scp>-GALACTAN EPITOPES
  作者：Qingfeng Pan、Yuguo Du、Fanzuo Kong*、Jingqi Pan、Mujian Lü

  DOI：10.1081/car-100104865

  日期：2001.4.30

  Two tetrameric arabinogalactans, β-D-galactopyranosyl-(1→6)-β-D-galactopyranosyl-(1→6)-[α-L-arabinofuranosyl-(1→3)]-D-galactopyranose (14) and α-L-arabinofuranosyl-(1→3)-β-D-galactopyranosyl-(1→6)-β-D-galactopyranosyl-(1→6)-D-galactopyranose (25), which are good candidates for CCRC-M7 epitope characterization, were synthesized efficiently using a convergent strategy. Migration of an acceptor acetyl

  两个四聚阿拉伯半乳聚糖，β- D-吡喃半乳糖-（1→6）-β- D-吡喃半乳糖-（1→6）-[α- L-阿拉伯呋喃糖基- （1→3）]- D-吡喃半乳糖（14）和α -L-阿拉伯呋喃糖基- （1→3）-β- D-吡喃半乳糖基-（1→6）-β- D-吡喃半乳糖基-（1→6）-D-吡喃半乳糖（25），它们是CCRC-M7的良好候选者抗原表位表征，使用收敛策略进行了有效合成。受体乙酰基的迁移被证明是合成的障碍，但是区域选择性糖基化或4- O受体的-苄基保护避免了这个问题，从而可以有效合成1→6连接的目标化合物。