benzyl O--(2->3)-O-(2,6-di-O-benzyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside | 126660-02-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl O--(2->3)-O-(2,6-di-O-benzyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside
• 英文别名: methyl (2S,4S,5R,6R)-5-acetamido-4-acetyloxy-2-[(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-5-(2,2-dimethylpropanoyloxy)-4,6-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-5-hydroxy-3-phenylmethoxy-6-(phenylmethoxymethyl)oxan-4-yl]oxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 126660-02-4
• 化学式: C₇₂H₈₇NO₂₄
• 分子量: 1350.48
• InChiKey: KEJBMOUUZLBPEC-IGVCHEMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  97
• 可旋转键数：
  38
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  299
• 氢给体数：
  2
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  benzyl O--(2->3)-O-(2,6-di-O-benzyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以94%的产率得到
  参考文献：
  名称：

  Synthesis of Ganglioside GD3 and its Comparison with Bovine GD3 with Regard to Oligodendrocyte Apoptosis Mitochondrial Damage

  摘要：

  2,3-Dehydroneuraminic acid derivative 5 was transformed in five efficient steps into sialyl donor 2, which has a phenylthio group on the beta-side of the 3-position for anchimeric assistance and a diethyl phosphite residue as leaving group at the anomeric carbon. The known GM3 intermediate 10 was transformed into the 4b,4c,8c-O-unprotected acceptor 3, which was then allowed to react with 2 by using TMSOTf as catalyst and acetonitrile as solvent to afford the desired tetrasaccharide 12, which has an alpha(2-8)-linkage between two neuraminic acid residues. Removal of the phenylthio group gave intermediate 13, which was transformed into O-tetraosyl trichloroacetimidate 16 as glycosyl donor. Application of the azidosphingosine glycosylation procedure furnished GD3 (1) in high overall yield. Comparison of synthetic GD3 with bovine-brain-derived GD3 showed that there were similar effects in GD3-triggered uncoupling of mitochondrial respiration and in induction of apoptosis in oligodendrocytes.

  DOI：

  10.1002/1521-3765(20010518)7:10<2178::aid-chem2178>3.0.co;2-e
• 作为产物：
  描述：

  benzyl O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside 、 甲基4,7,8,9-四-O-乙酰基-2-硫代-N-乙酰基-alpha-D-神经氨酸甲酯 在 4 A molecular sieve 、 苯基硒基三氟甲烷磺酸酯 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以5%的产率得到benzyl O--(2->3)-O-(2,6-di-O-benzyl-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzyl-2-O-pivaloyl-β-D-glucopyranoside
  参考文献：
  名称：

  苯甲烯基三氟甲磺酸盐作为硫糖苷的糖基化反应活化剂

  摘要：

  通过使用苯硒烯基三氟甲磺酸酯（PhSeOTf），开发了一种活化硫代糖苷的新方法，该方法与伯或仲糖HO-基团反应后，在极其温和的反应条件下提供了O-糖苷。该反应适用于各种1-硫代己糖苷2-6以及衍生自N-乙酰神经氨酸（NeuAc）的2-硫代糖苷20。

  DOI：

  10.1016/0008-6215(90)84078-9

文献信息

• Studies Directed toward the Synthesis of Polysialogangliosides: The Regio- and Stereocontrolled Synthesis of Rationally Designed Fragments of the Tetrasialoganglioside GQ_1b⁺.
  作者：Yukishige Ito、Shigeki Nunomura、Shohei Shibayama、Tomoya Ogawa

  DOI：10.1021/jo00032a601

  日期：1992.3

  The synthesis of suitably protected fragments of the tetrasialoganglioside GQ1b (I), i.e., 1 (alpha-NeuAc2 -->-8-alpha-NeuAc2 --> 3-beta-Gal1 --> 4Glc), 2 (alpha-NeuAc2 --> 8-alpha-NeuAc2 --> 3Gal), 3 (GalNAc), 4 (alpha-NeuAc2 --> 8NeuAc), 5 (beta-Gal1 -->- 3GalNAc), and 42 [beta-Gal1 --> 3-beta-GalNAc1 --> 4(alpha-NeuAc2 --> 3)beta-Gal --> 4Glc], is described. All are rationally designed so that the protecting groups can be regioselectively introduced and removed, as needed, before or after the stereoselective coupling of an appropriate pair of fragments. The syntheses of 1, 2, and 4 all feature stereoselective glycosylations by glycosyl donors that bear a C-3 thiophenoxy stereocontrolling auxiliary. Compound 3 was prepared from the D-glucosamine derivative 17 by way of a novel intramolecular nucleophilic displacement with inversion of configuration. Furthermore, model glycosylations of 4-hydroxygalactose derivatives, in which the thioglycoside 3 and the fluoride 40 served as glycosyl donors, were performed. The reaction of 3 with the glycosyl acceptor 30 gave the disaccharide 31 (GalNAc-beta-1 --> 4Gal), whereas that of 40 with 41 afforded the pentasaccharide 42.
• 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：——