methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside | 133198-04-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside
• 英文别名: Methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-beta-D-galactopyranoside；[(2R,3R,4R,5R,6S)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-methylsulfanyloxan-2-yl]methyl acetate
• CAS: 133198-04-6
• 化学式: C₂₁H₂₃NO₉S
• 分子量: 465.481
• InChiKey: QNHCRERIIKDXAI-YKGACUOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  151
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside 在 sodium methylate 、 肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 1.0h， 生成 苯甲酸,2-(氨基甲基)-,乙基酯
  参考文献：
  名称：

  The 2-N,N-Dibenzylamino Group as a Participating Group in the Synthesis ofβ-Glycosides

  摘要：

  The novel glycosyl donor 2-N,N-dibenzylaminothioglycoside 1 reacts with glycopyranoside alcohols 2, presumably via intermediate 3, to provide 1,2-trans-linked disaccharides 4 in high yield (78-86 %) and with high stereoselectivity. The N-benzyl protecting groups are readily cleaved under normal hydrogenolysis conditions, facilitating the synthesis of oligosaccharides with free amino groups.

  DOI：

  10.1002/(sici)1521-3773(19990201)38:3<346::aid-anie346>3.0.co;2-l
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranoside 、 三甲基甲硫基硅烷 、 、 二异丙胺 在 碳酸氢钠 、 水 、 Sodium sulfate-III 、 ethyl acetate heptane 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以Column chromatography (heptane-EtOAc) gave pure 20 (630 mg, 95%) as an amorphous powder的产率得到methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Ganglioside analogs

  摘要：

  公式（I）的神经节苷脂内酰胺类似物衍生物，其中A是通过虚线连接在2位的公式（II）的唾液酸残基；Z.sup.1是--OH或--NHX.sup.1基团，Y.sup.30是--CH.sub.3或--CH.sub.2 OH；X.sup.1和Y.sup.1共同形成键，Y.sup.2是--OH或--OR.sup.20基团，或者X.sup.1和Y.sup.2共同形成键，Y.sup.1是--OH或--NHAc；Y.sup.3是--OH或--OR.sup.20基团；R.sup.1是H或通过虚线连接在2位的公式（III）的唾液酸残基；Z.sup.2是--OH或--NHX.sup.2基团，Y.sup.30如上所定义；X.sup.2和Y.sup.10共同形成键，Y.sup.20是--OH，或者X.sup.2和Y.sup.20共同形成键，Y.sup.10是--OH；但是当R.sup.1是H时，Z.sup.1是--NHX.sup.1，当R.sup.1是公式（III）的唾液酸残基时，至少有一个Z.sup.1和Z.sup.2与--OH不同；R.sup.10是H、载体CA或--（糖）.sub.n基团。这些化合物是水解稳定的内酰胺类似物，空间上与天然存在的神经节苷脂内酯非常相似，具有抗原性并能够诱导产生与相应的神经节苷脂内酯交叉反应的抗体。

  公开号：

  US05637569A1

文献信息

• Synthesis of Ganglioside Lactams Corresponding to GM1-, GM2-, GM3-, and GM4-Ganglioside Lactones
  作者：Michael Wilstermann、Leonid O. Kononov、Ulf Nilsson、Asim K. Ray、Goeran Magnusson

  DOI：10.1021/ja00122a002

  日期：1995.5

  Ganglioside lactams are potentially useful analogs of ganglioside lactones, which are highly immunogenic derivatives of gangliosides. The lactam corresponding to the G(M3)-lactone saccharide has been synthesized by sialylation of a suitably protected lactose derivative carrying an azido group in the 2'-position, followed by reduction and ring closure to form G(M3)-lactam. Glycosylation in the 4-position of the central saccharide unit gave the G(M2)- and G(M1)- lactam saccharides. By a similar route, a 2-azido-Gal derivative was sialylated and treated as above to give the G(M4)-lactam saccharide. Deprotection gave the G(M2-4)-lactam saccharides in water soluble form, whereas attempted deprotection of the G(M1)-lactam caused its degradation. The G(M3)-lactam saccharide was coupled to ceramide, to afford the ganglioside lactam analog, and via a spacer to bovine serum albumin (BSA). The BSA conjugate was used as immunogen to raise monoclonal antibodies that cross-reacted with G(M3)-lactone. The antibodies were used in a histological staining of murine melanoma cells, clearly showing the presence of G(M3)-lactone on the cell surface. Keeping the G(M2-4)-lactam saccharides in D2O at 37 degrees C for 1 month caused marginal (0-11%) hydrolysis of the lactam ring.
• Synthesis of prospective disaccharide ligands for Escherichia coli O157 verotoxin
  作者：Christian Bernlind、Steven W. Homans、Robert A. Field

  DOI：10.1016/j.tetlet.2009.02.131

  日期：2009.7

  The synthesis of new potential ligands for Escherichia coli O157 verotoxin is reported, based on disaccharide fragments of the tetrasaccharide glycan portion of Gb(4) glycolipid. Intramolecular aglycone delivery was employed for the high-yielding and stereoselective production of the azidopropyl-tethered alpha-galactoside building block. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of the saccharide moiety of galactosylgloboside (SSEA-3) and its conjugation to bovine serum albumin and sepharose
  作者：Ulf Nilsson、Göran Magnusson

  DOI：10.1016/0008-6215(95)00044-t

  日期：1995.7

  The pentasaccharide glycoside corresponding to galactosylgloboside (SSEA-3), beta-D-Gal p-(1 --> 3)-beta-D-Gal pNAc-(1 --> 3)-alpha-D-Gal p-(1 --> 4)-beta-D-Gal p-(1 --> 4)-beta-D-Glc p-1-OCH2CH2Si-(CH3)(3) (4), was synthesized via glycosylation (87%) of 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-[2,3 ,6-tri-O-benzyl-4-O-(2,4,6-tri-O-benzyl-alpha-D-galactopyranosyl)-beta-D-galactopyranosyl]-beta-D-glucopyranoside (2) with the glycosyl donor methyl 4,6-di-O-acetyl-2-deoxy-2-phthalimido-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)- 1-thio-beta-D-galactopyranoside (1), followed by removal of protecting groups. Compound 4 was transformed into the spacer glycoside beta-D-Gal p-(1 --> 3)-beta-D-Gal pNAc-(1 --> 3)-alpha-D-Gal p-(1 --> 4)-beta-D-Gal p-(1 --> 4)-beta-D-Glc p-1-SCH2CH2COOH (10), which was coupled to bovine serum albumin (BSA), and Sepharose beads, to give the corresponding neoglycoprotein (11, 6 mol of saccharide/mol of BSA) and glycosylated Sepharose (12, 2.7 mu mol of saccharide/mL of sedimented beads), respectively. An improved synthesis of a protected globotetraoside beta-D-Gal pNAc-(1 --> 3)-alpha-D-Gal p-(1 --> 4)-beta-D-Gal p-(1 --> 4)-beta-D-Glc p-1-OCH(2)CH(2)SiMe(3) is also reported.
• ITO, YUKISHIGE;OGAWA, TOMOYA;NUMATA, MASAAKI;SUGIMOTO, MAMORU, CARBOHYDR. RES., 202,(1990) C. 165-175
  作者：ITO, YUKISHIGE、OGAWA, TOMOYA、NUMATA, MASAAKI、SUGIMOTO, MAMORU

  DOI：——

  日期：——
• US5637569A
  申请人：——

  公开号：US5637569A

  公开（公告）日：1997-06-10