phenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside | 299174-96-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside
• 英文别名: phenyl 2,3,3′,4,6,6′-hexa-O-benzyl-D-1-thio-β-lactoside；Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(b1-4)[Bn(-3)][Bn(-6)]Glc(b)-SPh；(2S,3R,4R,5R,6R)-4-phenylmethoxy-6-(phenylmethoxymethyl)-2-phenylsulfanyl-5-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-3-ol
• CAS: 299174-96-2
• 化学式: C₆₀H₆₂O₁₀S
• 分子量: 975.212
• InChiKey: JACWSHDWNOBYBZ-IJAHBILKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  71
• 可旋转键数：
  24
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  丁二酸酐 、 phenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside 在 4-二甲氨基吡啶 作用下， 以 吡啶 为溶剂， 反应 24.0h， 以85%的产率得到phenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-2-O-succinyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Prearranged Glycosides, Part 10. Intramolecular Glycosylation with Cellobiosyl, Lactosyl, and Maltosyl Donors

  摘要：

  Acetyl protected 1,2-O-(1-methoxyethylidene)-disaccharides 1 of maltose, cellobiose, and Lactose, respectively were converted via the corresponding benzyl protected couterparts 2, the benzyl protected phenyl 2-O-acetyl-3 and 2-O-unprotected 1-thio-glycoside disaccharides 4 into 2-O-succinoylated disaccharides 5. The latter were esterified with benzyl 2-O-benzoyl-4,6-di-O-benzylidene-alpha-D-glucopyranoside (6) to afford succinyl linked derivatives 7 the benzylidene groups of which were regioselectively opened to give prearranged glycoside trisaccharides 8. Intramolecular glycosylation of the latter with N-iodosuccinimide resulted in exclusive formation of the corresponding alpha-(1-->)-linked trisaccharides 9. No influence of the donor moiety on the diastereoselectivity of the intramolecular glycosylation was observed.

  DOI：

  10.1080/07328300008544113
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose 在 sodium methylate 、 mercury dibromide 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 36.0h， 生成 phenyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-3,6-di-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Prearranged Glycosides, Part 10. Intramolecular Glycosylation with Cellobiosyl, Lactosyl, and Maltosyl Donors

  摘要：

  Acetyl protected 1,2-O-(1-methoxyethylidene)-disaccharides 1 of maltose, cellobiose, and Lactose, respectively were converted via the corresponding benzyl protected couterparts 2, the benzyl protected phenyl 2-O-acetyl-3 and 2-O-unprotected 1-thio-glycoside disaccharides 4 into 2-O-succinoylated disaccharides 5. The latter were esterified with benzyl 2-O-benzoyl-4,6-di-O-benzylidene-alpha-D-glucopyranoside (6) to afford succinyl linked derivatives 7 the benzylidene groups of which were regioselectively opened to give prearranged glycoside trisaccharides 8. Intramolecular glycosylation of the latter with N-iodosuccinimide resulted in exclusive formation of the corresponding alpha-(1-->)-linked trisaccharides 9. No influence of the donor moiety on the diastereoselectivity of the intramolecular glycosylation was observed.

  DOI：

  10.1080/07328300008544113

文献信息

• Efficient Synthesis of 2-OH Thioglycosides from Glycals Based on the Reduction of Aryl Disulfides by NaBH4
  作者：Yang-Fan Guo、Tao Luo、Guang-Jing Feng、Chun-Yang Liu、Hai Dong

  DOI：10.3390/molecules27185980

  日期：——

  An improved method to efficiently synthesize 2-OH thioaryl glycosides starting from corresponding per-protected glycals was developed, where 1,2-anhydro sugars were prepared by the oxidation of glycals with oxone, followed by reaction of crude crystalline 1,2-anhydro sugars with NaBH4 and aryl disulfides. This method has been further used in a one-pot reaction to synthesize glycosyl donors having both

  开发了一种从相应的过保护糖苷开始有效合成 2-OH 硫代芳基糖苷的改进方法，其中 1,2-脱水糖是通过糖醛与过氧化氢进行氧化，然后与粗结晶 1,2-脱水糖反应制备的。与 NaBH 4和芳基二硫化物。该方法已进一步用于一锅反应，以合成具有“武装”和“NGP（邻接组参与）”效应的糖基供体。
• Prearranged Glycosides, Part 10. Intramolecular Glycosylation with Cellobiosyl, Lactosyl, and Maltosyl Donors
  作者：Gregor Lemanski、Thorsten Lindenberg、Hassan Fakhrnabavi、Thomas Ziegler

  DOI：10.1080/07328300008544113

  日期：2000.1

  Acetyl protected 1,2-O-(1-methoxyethylidene)-disaccharides 1 of maltose, cellobiose, and Lactose, respectively were converted via the corresponding benzyl protected couterparts 2, the benzyl protected phenyl 2-O-acetyl-3 and 2-O-unprotected 1-thio-glycoside disaccharides 4 into 2-O-succinoylated disaccharides 5. The latter were esterified with benzyl 2-O-benzoyl-4,6-di-O-benzylidene-alpha-D-glucopyranoside (6) to afford succinyl linked derivatives 7 the benzylidene groups of which were regioselectively opened to give prearranged glycoside trisaccharides 8. Intramolecular glycosylation of the latter with N-iodosuccinimide resulted in exclusive formation of the corresponding alpha-(1-->)-linked trisaccharides 9. No influence of the donor moiety on the diastereoselectivity of the intramolecular glycosylation was observed.