methyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-galactopyranoside | 91298-39-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-galactopyranoside
• 英文别名: Gal2Ac3Ac4Ac6Ac(b1-6)b-Gal1Me2Ac3Ac4Ac；[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-methoxyoxan-2-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 91298-39-4
• 化学式: C₂₇H₃₈O₁₈
• 分子量: 650.588
• InChiKey: PGJHXPDHJYQJOE-WPDXXWPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  45
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  221
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-galactopyranoside 生成 (2R,3R,5R,6R)-2-(hydroxymethyl)-6-[[(2R,3R,5R,6R)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]methoxy]oxane-3,4,5-triol
  参考文献：
  名称：

  HLAVATY, J.;KARACSONYI, S.;ALFOLDI, J., CHEM. PAP., 42,(1988) N 4, C. 519-525

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-6-O-(chloroacetyl)-α-D-galactopyranosyl bromide 在 palladium on activated charcoal 、 氰化汞 、 mercury dibromide calcium sulfate 、 氢气 、 碳酸氢钠 作用下， 以 乙醇 、 丙酮 、 苯 为溶剂， 反应 19.0h， 生成 methyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-galactopyranoside
  参考文献：
  名称：

  甲基O-（3-脱氧-3-氟-β-d-吡喃半乳糖苷）-（1→6）-β-d-吡喃半乳糖苷和甲基O-（3-脱氧-3-氟-β-d-吡喃半乳糖苷）-（1→6）-O-β-d-吡喃半乳糖苷-（1→6）-β-d-吡喃半乳糖苷

  摘要：

  2,4,6-三-O-乙酰基-3-脱氧-3-氟-α-d-吡喃半乳糖基溴化物（3）与2,3,4-三-O-乙酰基-β-d-吡喃半乳糖苷甲基的缩合（4）得到在3′-位氟化的完全乙酰化的（1→6）-β-d-半乳糖二糖，将其脱乙酰化得到标题二糖。通过将4与2,3,4-三-O-乙酰基-6-O-氯乙酰基-α-d-吡喃半乳糖基溴化物（5）反应，将形成的甲基O-（2,3， 4-三-O-乙酰基-6-O-氯乙酰基-β-d-吡喃半乳糖苷）-（1→6）-2,3,4-三-O-乙酰基-β-d-吡喃半乳糖苷得到甲基O-（ 2,3,4-三-O-乙酰基-β-d-吡喃半乳糖苷）-（1→6）-2,3,4-三-O-乙酰基-β-d-吡喃半乳糖苷（14），与3缩合，和脱乙酰。甲基O-（2,3,4-三-O-乙酰基-6-O-氯乙酰基-β-d-吡喃半乳糖基）-（1→6）-O-（2,3，通过将二糖14与溴化物5缩合而获得的4-三-O-乙酰基-β-d-吡喃半乳糖苷-（1→6）-2

  DOI：

  10.1016/0008-6215(85)85128-4

文献信息

• Glycosylation chemistry promoted by iodine monobromide: Efficient synthesis of glycosyl bromides from thioglycosides, and O-glycosides from ‘disarmed’ thioglycosides and glycosyl bromides
  作者：K.P. Ravindranathan Kartha、Robert A. Field

  DOI：10.1016/s0040-4039(97)10124-1

  日期：1997.11

  reagent for the conversion of both ‘armed’ and ‘disarmed’ thioglycosides (SMe, SPri, SPh) into glycosyl bromides. This reagent is compatible with most common protecting groups, and O-glycosidic linkages. The additional potency of IBr, compared to iodine, as an iodonium ion source also permits the glycosylation of sugar alcohols by ‘disarmed’ glycosyl bromides and thioglycosides.

  一溴化碘已被发现是用于转化的有效试剂既“武装”和“解除”硫代糖苷（SMe，SPr我，SPh）转换成糖基溴化物。该试剂与最常见的保护基和O-糖苷键兼容。与碘相比，作为碘离子源，IBr的附加效力还允许糖基糖通过“解除武装”的糖基溴化物和硫代糖苷进行糖基化。
• Synthesis and characterization of methyl 6-O-α- and -β-d-galactopyranosyl-β-d-galactopyranoside
  作者：Pavol Kováč、Edward A. Sokoloski、Cornelis P.J. Glaudemans

  DOI：10.1016/0008-6215(84)85088-0

  日期：1984.5

  disaccharides (7 and 9, respectively) in high yield, and their structure was confirmed by 1H- and 13C-n.m.r. 1d. and 2d. spectroscopy. O-Deacetylation of 7 gave the hitherto unknown, crystalline methyl 6-O-alpha-D-galactopyranosyl-beta-D-galactopyranoside. O-Deacetylation of 9 gave the corresponding, beta-D-linked disaccharide methyl glycoside, the physical constants of which are discussed with respect to controversial

  依次对甲基β-D-吡喃半乳糖苷进行三苯甲基化，乙酰化和去三苯甲基化，得到结晶的甲基2,3,4-三-O-乙酰基-β-D-吡喃半乳糖苷（4）和甲基2,3,6-三-O-乙酰基-甲基β-D-吡喃半乳糖苷，后者是乙酰迁移引起的次要产物。在氰化汞和溴化汞的存在下，4与2,3,4,6-四-O-乙酰基-α-D-半乳糖基溴在苯中的反应得到α-和β-D-（1-- --6）-连接的二糖（分别为7和9），产率很高，其结构由1H-和13C-nmr 1d证实。和2d。光谱学。7的O-脱乙酰化产生了迄今未知的结晶甲基6-O-α-D-吡喃半乳糖基-β-D-吡喃半乳糖苷。9的O-脱乙酰基化得到相应的β-D连接的二糖甲基糖苷，
• Glycosylation by sugar 1,2-O-(1-cyanobenzylidene) derivatives: influence of glycosyl-donor structure and promoter
  作者：Nicolai K. Kochetkov、Vitaly I. Betaneli、Irina A. Kryazhevskikh、Andrey Ya. Ott

  DOI：10.1016/0008-6215(93)80006-z

  日期：1993.5

  3,4,6-Tri-O-acetyl-1,2-O-(1-cyanobenzylidene)-alpha-D-galactopyranoses with differently substituted aromatic nuclei have been synthesised and used as glycosyl donors in reactions with the acceptors methyl 2,3,4-tri-O-acetyl-6-O-trityl-beta-D-galactopyranoside (11) and methyl 2,4,6-tri-O-acetyl-3-O-trityl-beta-D-galactopyranoside (12). The glycosylation of 11 gave only beta products. The efficiency and stereoselectivity of the glycosylations of 12 depend on the nature of the substituent in the aromatic ring. The stereoselectivity for the formation of 1,2-trans-glycosidic bonds was the highest with the p-methoxy-benzylidene derivative with triphenylmethylium triflate as the promoter.
• Enzymatic syntheses and selective hydrolysis of O-β-d-galactopyranosides using a marine mollusc β-galactosidase
  作者：Assunta Giordano、Annabella Tramice、Giuseppina Andreotti、Ernesto Mollo、Antonio Trincone

  DOI：10.1016/j.bmcl.2004.10.016

  日期：2005.1

  The use of crude extract of the hepatopancreas of Aplysia fasciata, a large mollusc belonging to the order Anaspidea containing a beta-galactosidase activity, was reported for the synthesis of different galactosides. Good yields with polar acceptors and the uncommon beta-1-3 selectivity in the transgalactosylation reactions with most of the acceptors were observed. A beta-1-2 selectivity in the hydrolytic conditions was also observed and discussed. (C) 2004 Elsevier Ltd. All rights reserved.
• Betaneli, V. I.; Kryazhevskikh, I. A.; Kochetkov, N. K., Doklady Chemistry, 1992, vol. 322, p. 12 - 14
  作者：Betaneli, V. I.、Kryazhevskikh, I. A.、Kochetkov, N. K.

  DOI：——

  日期：——