Gal2Ac3Ac4Ac6Ac(b1-3)b-Gal1Me2Ac4Ac6Ac | 102854-37-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Gal2Ac3Ac4Ac6Ac(b1-3)b-Gal1Me2Ac4Ac6Ac
• 英文别名: [(2R,3S,4S,5R,6R)-3,5-diacetyloxy-6-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 102854-37-5
• 化学式: C₂₇H₃₈O₁₈
• 分子量: 650.588
• InChiKey: UHSQXNOZAXQAJT-PQPUEWTKSA-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：

  Gal2Ac3Ac4Ac6Ac(b1-3)b-Gal1Me2Ac4Ac6Ac 在 三氟甲磺酸三甲基硅酯 4 A molecular sieve 、 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 53.0h， 生成 8-Methoxycarbonyloctyl-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-2-azido-4,6-di-O-benzoyl-2-desoxy-α-D-galactopyranosid
  参考文献：
  名称：

  Entwicklung Eines合成3-der-O-β-d-吡喃半乳糖基-d-吡喃半乳糖

  摘要：

  摘要在三氟甲磺酸三甲基甲硅烷基酯存在下，1,2,3,4,6-戊基-O-乙酰基-β-d-吡喃半乳糖与苄基4-O-乙酰基-2,6-二-O-苄基-β-反应d-吡喃半乳糖苷得到苄基2,6-二-O-苄基-3-O-β-d-吡喃半乳糖苷-β-d-吡喃半乳糖苷进一步转化为合成的1,2,4,6-四-O-乙酰基嵌段-3-O-（2,3,4,6-四-O-乙酰基-β-d-吡喃半乳糖基）-β-d-吡喃半乳糖。这在路易斯酸催化剂存在下并与相应的糖基受体一起，得到8-甲氧基羰基辛基3-O-β-d-吡喃半乳糖苷-β-d-吡喃半乳糖苷和8-甲氧基羰基辛基O-β-d-吡喃半乳糖苷-（1 →3）-O-β-d-吡喃半乳糖苷-（1→3）-2-乙酰氨基-2-脱氧-α-d-吡喃半乳糖苷。

  DOI：

  10.1016/0008-6215(85)85005-9
• 作为产物：
  描述：

  methyl 3,4-di-O-isopropylidene-β-D-galactopyranoside 在 吡啶 、 2,4,6-三甲基吡啶 、 4-二甲氨基吡啶 、 triphenylmethyl perchlorate 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 19.75h， 生成 Gal2Ac3Ac4Ac6Ac(b1-3)b-Gal1Me2Ac4Ac6Ac
  参考文献：
  名称：

  Glycosylation by sugar 1,2-O-(1-cyanobenzylidene) derivatives: influence of glycosyl-donor structure and promoter

  摘要：

  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.

  DOI：

  10.1016/0008-6215(93)80006-z

文献信息

• Tandem Exploitation ofHelix pomatia Glycosyltransferases: Facile Syntheses of H-Antigen-Bearing Oligosaccharides
  作者：Hagen Bretting、Friedrich Buck、Günter Jacobs、Sebastian Meinke、Angela M. Scheppokat、Joachim Thiem

  DOI：10.1002/chem.200700440

  日期：2007.8.27

  in a membrane preparation of these glands. These were used to synthesise various oligosaccharides by successive addition of the NDP-activated (NDP=nucleoside-5'-diphosphate) D-Gal or L-Fuc moieties, up to a heptasaccharide by starting from the disaccharide D-Gal-beta(1-->3)-D-Gal-beta(1-->OMe. Even larger oligosaccharides up to a tridecasaccharide were obtained by starting with the hexasaccharide D-

  Helicidae家族的蜗牛在其蛋白腺中产生高度分支的半乳聚糖，该半乳聚糖几乎仅由D-和L-半乳糖组成。D-Gal残基糖基地通过beta（1-> 6）-或beta（1-> 3）连接，而L-Gal部分则连接alpha（1-> 2）。到目前为止，在这些腺体的膜制剂中已鉴定出两种β（1-> 6）-D-半乳糖基转移酶和一种α（1-> 2）-L-半乳糖基转移酶。通过连续添加NDP活化的（NDP = nucleoside-5'-diphosphate）D-Gal或L-Fuc部分将它们用于合成各种寡糖，从二糖D-Gal-beta（1 -> 3）-D-Gal-β（1-> OMe。从六糖D-Gal-β（1-> 3）-D-Gal]4-β（1→4）-D-Glc作为受体底物。这种串联开发过程具有将D-Gal和L-Fuc残基轻松引入各种寡糖的巨大潜力，这些寡糖可用于配体/受体研究。
• 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。
• 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.
• Porcine liver (2 → 3)-α-sialyltransferase: substrate specificity studies and application of the immobilized enzyme to the synthesis of various sialylated oligosaccharide sequences
  作者：André Lubineau、Karine Basset-Carpentier、Claudine Augé

  DOI：10.1016/s0008-6215(97)00043-8

  日期：1997.5

  In search of substrate analogues for the porcine liver beta-D-Galp-(1 --> 3)-D-Galp-NAc: CMP-Neu5Ac-(2 --> 3')-alpha-sialyltransferase, three disaccharides beta-D-Galp-(1 --> 3)-beta-D-Galp-O-CH3 (5), beta-D-Galp-(1 --> 3)-beta-D-(2-OAc)-Galp-O-CH3 (7) and beta-D-Galp-(1 --> 3)-beta-D-(2-OAc)-Galp-O-Bn (11) were synthesized and tested with the enzyme. Disaccharide 7 turned out to be a very good substrate allowing a rapid access to the trisaccharide alpha-Neu5Ac-(2 --> 3)-beta-D-Galp-(1 --> 3)-P-D-(2-OAc)-Galp-O-CH3 (13) on a preparative scale using the crude enzyme immobilized on cationic exchanger. Trisaccharide 13 was further exploited, first as a sialyl donor in Trypanosoma cruzi trans-sialidase catalyzed reaction and second through acetolysis reaction as a source for the synthon alpha-Neu5Ac-(2 --> 3)-D-Gal (16). (C) 1997 Elsevier Science Ltd.
• BETANELI, V. I.;KRYAZHEVSKIX, I. A.;OTT, A. YA.;KOCHETKOV, N. K., BIOORGAN. XIMIYA, 15,(1989) N, S. 217-230
  作者：BETANELI, V. I.、KRYAZHEVSKIX, I. A.、OTT, A. YA.、KOCHETKOV, N. K.

  DOI：——

  日期：——