3,4,6-tri-O-acetyl-1,2-(1-O-allyl-3,4,6-tri-O-benzyl-2S-β-D-glucopyranos-2-yl)-orthoacetate | 170452-34-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-acetyl-1,2-(1-O-allyl-3,4,6-tri-O-benzyl-2S-β-D-glucopyranos-2-yl)-orthoacetate
• CAS: 170452-34-3
• 化学式: C₄₄H₅₂O₁₄S
• 分子量: 836.954
• InChiKey: SWHZXUHCKOYIED-YGKWNDPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  59.0
• 可旋转键数：
  19.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  152.74
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-1,2-(1-O-allyl-3,4,6-tri-O-benzyl-2S-β-D-glucopyranos-2-yl)-orthoacetate 在 4 A molecular sieve 、 三乙基硅基三氟甲磺酸酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 allyl 2-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-3,4,6-tri-O-benzyl-2-thio-β-D-glucopyranoside 、 allyl 2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3,4,6-tri-O-benzyl-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 4 A molecular sieve 、 三乙基硅基三氟甲磺酸酯 、 sodium methylate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 2.08h， 生成 3,4,6-tri-O-acetyl-1,2-(1-O-allyl-3,4,6-tri-O-benzyl-2S-β-D-glucopyranos-2-yl)-orthoacetate
  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