allyl 3,4,6-tri-O-benzyl-2-thio-β-D-gluco-pyranoside | 170452-30-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3,4,6-tri-O-benzyl-2-thio-β-D-gluco-pyranoside
• CAS: 170452-30-9
• 化学式: C₃₀H₃₄O₅S
• 分子量: 506.663
• InChiKey: VTZNDHYHBHDHPI-CMPUJJQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  36.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.15
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  allyl 3,4,6-tri-O-benzyl-2-thio-β-D-gluco-pyranoside 在 palladium on activated charcoal 4 A molecular sieve 、 氢气 、 三乙基硅基三氟甲磺酸酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 溶剂黄146 为溶剂， -10.0 ℃ 、344.73 kPa 条件下， 反应 73.5h， 生成 n-propyl 2-O-(α-D-glucopyranosyl)-2-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a thio analogue of n-propyl kojibioside, a potential glucosidase inhibitor

  摘要：

  The disaccharide alpha-D-Glc p-(1-S-2)-beta-D-Glc p-(1-O Pr) 1, a thio analogue of alpha-D-Glc p-(1 --> 2)-alpha-D-Glc p-(1-OPr)(n-propyl kojibioside) in which the inter-glycosidic oxygen atom is replaced by sulfur, has been synthesized for evaluation as a potential glucosidase inhibitor. Glycosylation of the 2-thiol glucopyranosyl acceptor 4 with the trichloroacetimidate of 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranose 5 gave the alpha-linked disaccharide 6 stereoselectively. Deprotection was performed by hydrogenolysis in the presence of Pd/C to give 1 as the beta-n-propyl glycoside. Glycosylation of the thiol 4 with the trichloroacetimidate of 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranose 8 gave a 1:2.3 mixture of the alpha and beta disaccharides (9 and 10); evidence is presented for the occurrence of the orthoester 11, as an intermediate in the formation of the beta-disaccharide.

  DOI：

  10.1016/0008-6215(95)00014-k
• 作为产物：
  描述：

  allyl 3,4,6-tri-O-benzyl-2-S-acetyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以97%的产率得到allyl 3,4,6-tri-O-benzyl-2-thio-β-D-gluco-pyranoside
  参考文献：
  名称：

  Synthesis of a thio analogue of n-propyl kojibioside, a potential glucosidase inhibitor

  摘要：

  The disaccharide alpha-D-Glc p-(1-S-2)-beta-D-Glc p-(1-O Pr) 1, a thio analogue of alpha-D-Glc p-(1 --> 2)-alpha-D-Glc p-(1-OPr)(n-propyl kojibioside) in which the inter-glycosidic oxygen atom is replaced by sulfur, has been synthesized for evaluation as a potential glucosidase inhibitor. Glycosylation of the 2-thiol glucopyranosyl acceptor 4 with the trichloroacetimidate of 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranose 5 gave the alpha-linked disaccharide 6 stereoselectively. Deprotection was performed by hydrogenolysis in the presence of Pd/C to give 1 as the beta-n-propyl glycoside. Glycosylation of the thiol 4 with the trichloroacetimidate of 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranose 8 gave a 1:2.3 mixture of the alpha and beta disaccharides (9 and 10); evidence is presented for the occurrence of the orthoester 11, as an intermediate in the formation of the beta-disaccharide.

  DOI：

  10.1016/0008-6215(95)00014-k