Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(a1-4)[Bn(-6)]Gal2Ac3Ac(a1-3)[Bn(-2)][Bn(-4)]a-Rha1Me | 204704-86-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(a1-4)[Bn(-6)]Gal2Ac3Ac(a1-3)[Bn(-2)][Bn(-4)]a-Rha1Me
• 英文别名: [(2R,3R,4S,5S,6R)-3-acetyloxy-2-[(2R,3R,4R,5S,6S)-2-methoxy-6-methyl-3,5-bis(phenylmethoxy)oxan-4-yl]oxy-6-(phenylmethoxymethyl)-5-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-4-yl] acetate
• CAS: 204704-86-9
• 化学式: C₇₂H₈₀O₁₇
• 分子量: 1217.42
• InChiKey: QIAXOPWYFZIGNE-ZLDZOUGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  89
• 可旋转键数：
  32
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  173
• 氢给体数：
  0
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(a1-4)[Bn(-6)]Gal2Ac3Ac(a1-3)[Bn(-2)][Bn(-4)]a-Rha1Me 在 磺酰氯 、 三氟甲磺酸 、 4 A molecular sieve 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 methyl (3aR,4R,6R,7S,7aS)-4-[(2R,3R,4R,5S,6S)-2-methoxy-6-methyl-3,5-bis(phenylmethoxy)oxan-4-yl]oxy-2-methyl-6-(phenylmethoxymethyl)-7-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)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：

  ethyl 4,6-O-benzylidene-2,3-di-O-para-methoxybenzyl-1-thio-β-D-galactopyranoside 在 吡啶 、 盐酸 、 3 A molecular sieve 、 4 A molecular sieve 、 四丁基溴化铵 、 sodium cyanoborohydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氟甲烷磺酸甲酯 、 copper(ll) bromide 作用下， 以 乙醚 、 二氯甲烷 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 110.75h， 生成 Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(a1-4)[Bn(-6)]Gal2Ac3Ac(a1-3)[Bn(-2)][Bn(-4)]a-Rha1Me
  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