phenyl 4,6-O-benzylidene-2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside | 250123-35-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 4,6-O-benzylidene-2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside
• 英文别名: [(2R,4aR,6S,7R,8S,8aS)-7-benzoyloxy-2-phenyl-6-phenylsulfanyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] benzoate
• CAS: 250123-35-4
• 化学式: C₃₃H₂₈O₇S
• 分子量: 568.647
• InChiKey: FHEADONXPBDQPJ-CEYGQUMMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  41
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  phenyl 4,6-O-benzylidene-2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside 在 三氟化硼乙醚 、 对甲苯磺酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.5h， 生成 phenyl 2,3-di-O-benzoyl-4,6-O-[(R)-1-methoxycarbonylethylidene]-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of glycoimmunogen Tn-Thr-PS A1 via hydrazone bond and stability optimization of PS A1 monosaccharide mimics under vaccine development conditions

  摘要：

  Previously, our group constructed several immunogens utilizing oxime linkage to conjugate a T-cell stimulatory zwitterionic polysaccharide PS A1 and tumor associated carbohydrate antigens (TACAs) in acetate buffer. Here, a semi-synthetic immunogen was synthesized using hydrazone conjugation between PS A1 and a glycopeptide hydrazide (alpha-D-GalNAc-L-Thr-NH-NH2) with an excellent loading in PBS buffer. To get robust immune response, the retention of zwitterionic character of PS A1 under vaccine construction conditions is essential. In this regard, the stability of embedded pyruvate acetal moiety in tetrasaccharide repeating unit of PS A1 can validate the retention of the dual charges. Therefore, rather than utilizing this highly immunogenic PS A1 fully, stability studies were performed with synthetic 1-thiophenyl-4,6-O-pyruvate acetal-D-galactopyranose in varying acetate buffer pHs and time intervals. Furthermore, 1-propyl-D-galactofuranose was synthesized to mimick the D-Galf of PS A1 to examine regioselective hydrazone and oxime formation with alpha-D-GalNAc-L-Thr-NH-NH2 and alpha-D-GalNAc-ONH2 moieties respectively.

  DOI：

  10.1080/07328303.2019.1709975
• 作为产物：
  描述：

  苯基-1-硫醇-beta-D-半乳糖苷 在 吡啶 、 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 phenyl 4,6-O-benzylidene-2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthetic Studies on Glycosphingolipids from Protostomia Phyla: Synthesis of Neogala-Series Glycolipid Analogues Containing a Mannose Residue from the Earthworm Pheretima hilgendorfi.

  摘要：

  从蚯蚓 Pheretima hilgendorfi 中合成了以下两种糖磷脂类似物：三糖 2-(十四烷基)十六烷基 α-D-吡喃甘露糖基-(1→4)-β-D-吡喃半乳糖基-(1→6)-β-D-吡喃半乳糖苷 (13) 和四糖 2-(十四烷基)十六烷基 α-D-半乳糖苷-(1→6)-[α-D-吡喃甘露糖基-(1→4)]-β-D-吡喃半乳糖苷-(1→6)-β-D-吡喃半乳糖苷(20)是通过逐步缩合适当保护的单糖单元合成的。2-(trimethylsilyl)ethyl 2, 3, 4-tri-O-benzoyl-β-D-galactopyranoside 衍生物 (5) 用作糖基受体，D-半乳糖和 D-甘露糖的硫代苯衍生物分别用作供体。

  DOI：

  10.1248/cpb.47.1265

文献信息

• Synthetic Studies on Glycosphingolipids from Protostomia Phyla: Synthesis of Neogala-Series Glycolipid Analogues Containing a Mannose Residue from the Earthworm Pheretima hilgendorfi.
  作者：Noriyasu HADA、Akiko MATSUSAKI、Mutsumi SUGITA、Tadahiro TAKEDA

  DOI：10.1248/cpb.47.1265

  日期：——

  Two kinds of glycosphingolipid analogues from the earthworm Pheretima hilgendorfi were synthesized as follows : the trisaccharide 2-(tetradecyl)hexadecyl α-D-mannopyranosyl-(1→4)-β-D-galactopyranosyl-(1→6)-β-D-galactopyranoside (13) and the tetrasaccharide 2-(tetradecyl) hexadecyl α-D-galactopyranosyl-(1→6)-[α-D-mannopyranosyl-(1→4)]-β-D-galactopyranosyl-(1→6)-β-D-galactpyranoside (20) were synthesized by stepwise condensation of suitably protected monosaccharide units. A 2-(trimethylsilyl)ethyl 2, 3, 4-tri-O-benzoyl-β-D-galactopyranoside derivative (5) was used as the glycosyl acceptor and thiophenyl derivatives of D-galactose and D-mannose were used as donors respectively.

  从蚯蚓 Pheretima hilgendorfi 中合成了以下两种糖磷脂类似物：三糖 2-(十四烷基)十六烷基 α-D-吡喃甘露糖基-(1→4)-β-D-吡喃半乳糖基-(1→6)-β-D-吡喃半乳糖苷 (13) 和四糖 2-(十四烷基)十六烷基 α-D-半乳糖苷-(1→6)-[α-D-吡喃甘露糖基-(1→4)]-β-D-吡喃半乳糖苷-(1→6)-β-D-吡喃半乳糖苷(20)是通过逐步缩合适当保护的单糖单元合成的。2-(trimethylsilyl)ethyl 2, 3, 4-tri-O-benzoyl-β-D-galactopyranoside 衍生物 (5) 用作糖基受体，D-半乳糖和 D-甘露糖的硫代苯衍生物分别用作供体。
• Synthesis of glycoimmunogen Tn-Thr-PS A1 <i>via</i> hydrazone bond and stability optimization of PS A1 monosaccharide mimics under vaccine development conditions
  作者：F. Hossain、S. Nishat、S. Ghosh、S. Boga、G. T. Hymel、P. R. Andreana

  DOI：10.1080/07328303.2019.1709975

  日期：2020.3.23

  Previously, our group constructed several immunogens utilizing oxime linkage to conjugate a T-cell stimulatory zwitterionic polysaccharide PS A1 and tumor associated carbohydrate antigens (TACAs) in acetate buffer. Here, a semi-synthetic immunogen was synthesized using hydrazone conjugation between PS A1 and a glycopeptide hydrazide (alpha-D-GalNAc-L-Thr-NH-NH2) with an excellent loading in PBS buffer. To get robust immune response, the retention of zwitterionic character of PS A1 under vaccine construction conditions is essential. In this regard, the stability of embedded pyruvate acetal moiety in tetrasaccharide repeating unit of PS A1 can validate the retention of the dual charges. Therefore, rather than utilizing this highly immunogenic PS A1 fully, stability studies were performed with synthetic 1-thiophenyl-4,6-O-pyruvate acetal-D-galactopyranose in varying acetate buffer pHs and time intervals. Furthermore, 1-propyl-D-galactofuranose was synthesized to mimick the D-Galf of PS A1 to examine regioselective hydrazone and oxime formation with alpha-D-GalNAc-L-Thr-NH-NH2 and alpha-D-GalNAc-ONH2 moieties respectively.