Acetic acid (2R,3R,4S,5S,6R)-4-acetoxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-5-hydroxy-tetrahydro-pyran-3-yl ester | 204704-85-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2R,3R,4S,5S,6R)-4-acetoxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-5-hydroxy-tetrahydro-pyran-3-yl ester
• 英文别名: Bn(-6)Gal2Ac3Ac(a1-3)[Bn(-2)][Bn(-4)]a-Rha1Me；[(2R,3R,4S,5S,6R)-3-acetyloxy-5-hydroxy-2-[(2R,3R,4R,5S,6S)-2-methoxy-6-methyl-3,5-bis(phenylmethoxy)oxan-4-yl]oxy-6-(phenylmethoxymethyl)oxan-4-yl] acetate
• CAS: 204704-85-8
• 化学式: C₃₈H₄₆O₁₂
• 分子量: 694.776
• InChiKey: RSADRYOTNSASIN-WBXWBPSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  50
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5S,6R)-4-acetoxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-5-hydroxy-tetrahydro-pyran-3-yl ester 在 palladium on activated charcoal 磺酰氯 、 三氟甲磺酸 、 4 A molecular sieve 、 氢气 、 sodium methylate 、 三氟甲烷磺酸甲酯 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 95.0h， 生成 methyl (3aR,4R,6R,7S,7aS)-4-[(2R,3R,4R,5S,6S)-3,5-dihydroxy-2-methoxy-6-methyloxan-4-yl]oxy-6-(hydroxymethyl)-2-methyl-7-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2-carboxylate
  参考文献：
  名称：

  Preparation oftransDiequatorial 2,3-Pyruvate Acetals in a Di- and a Trisaccharide Related to the K-Antigen from E. Coli 0101:K103:H⁻

  摘要：

  Using methyl 2,2-bis(ethylthio)propionate as acetalating agent and triflic acid-sulfuryl chloride as catalyst, synthesis of 2,3-trans diequatorial pyruvate ketal was achieved. Starting from D-galactose and L-rhamnose derivatives, methyl 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl-(1-->4)-6-O-benzyl-2,3-O-(1-methoxycarbonyl)ethylidene- alpha-D-galactopyranosyl- (1-->3)-2,4-di-O-benzyl-alpha-L-rhamnopyranoside and methyl 4,6-di-O-benzyl-2,3-O-(1-methoxycarbonyl)ethylidene-alpha-D-galactopyranosyl-(1-->3)-2,4-di-O-benzyl-alpha-L-rhamnopyranoside were synthesized. Removal of the protecting groups from the former, afforded the trisaccharide repeating unit of the K-antigen from E.coli O101:K103:H- in the form of its methyl glycoside methyl ester.

  DOI：

  10.1080/00397919808006846
• 作为产物：
  描述：

  Acetic acid (4aR,6R,7R,8S,8aS)-8-acetoxy-6-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 在 盐酸 、 3 A molecular sieve 、 sodium cyanoborohydride 作用下， 以 乙醚 为溶剂， 反应 0.75h， 以79%的产率得到Acetic acid (2R,3R,4S,5S,6R)-4-acetoxy-6-benzyloxymethyl-2-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-5-hydroxy-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Preparation oftransDiequatorial 2,3-Pyruvate Acetals in a Di- and a Trisaccharide Related to the K-Antigen from E. Coli 0101:K103:H⁻

  摘要：

  Using methyl 2,2-bis(ethylthio)propionate as acetalating agent and triflic acid-sulfuryl chloride as catalyst, synthesis of 2,3-trans diequatorial pyruvate ketal was achieved. Starting from D-galactose and L-rhamnose derivatives, methyl 2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl-(1-->4)-6-O-benzyl-2,3-O-(1-methoxycarbonyl)ethylidene- alpha-D-galactopyranosyl- (1-->3)-2,4-di-O-benzyl-alpha-L-rhamnopyranoside and methyl 4,6-di-O-benzyl-2,3-O-(1-methoxycarbonyl)ethylidene-alpha-D-galactopyranosyl-(1-->3)-2,4-di-O-benzyl-alpha-L-rhamnopyranoside were synthesized. Removal of the protecting groups from the former, afforded the trisaccharide repeating unit of the K-antigen from E.coli O101:K103:H- in the form of its methyl glycoside methyl ester.

  DOI：

  10.1080/00397919808006846