(2R,3S,4S,5R,6R)-6-((2R,3R,4R,5S,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-2-hydroxymethyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol | 204704-90-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S,5R,6R)-6-((2R,3R,4R,5S,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-2-hydroxymethyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol
• 英文别名: Mob(-2)[Mob(-3)]Gal(a1-3)[Bn(-2)][Bn(-4)]a-Rha1Me；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(2R,3R,4R,5S,6S)-2-methoxy-6-methyl-3,5-bis(phenylmethoxy)oxan-4-yl]oxy-4,5-bis[(4-methoxyphenyl)methoxy]oxan-3-ol
• CAS: 204704-90-5
• 化学式: C₄₃H₅₂O₁₂
• 分子量: 760.879
• InChiKey: RNQYEVZHKSIPSA-JWIXYJLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  55
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6R)-6-((2R,3R,4R,5S,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-2-hydroxymethyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol 在 磺酰氯 、 三氟甲磺酸 、 4 A molecular sieve 、 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (3aR,4R,6R,7S,7aS)-7-Benzyloxy-6-benzyloxymethyl-4-((2R,3R,4R,5S,6S)-3,5-bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-2-methyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2-carboxylic acid methyl 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
• 作为产物：
  描述：

  (4aR,6R,7R,8S,8aS)-6-((2R,3R,4R,5S,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-7,8-bis-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 在 溶剂黄146 作用下， 反应 2.0h， 以100%的产率得到(2R,3S,4S,5R,6R)-6-((2R,3R,4R,5S,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-yloxy)-2-hydroxymethyl-4,5-bis-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-ol
  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

文献信息

• Preparation of<i>trans</i>Diequatorial 2,3-Pyruvate Acetals in a Di- and a Trisaccharide Related to the K-Antigen from E. Coli 0101:K103:H⁻
  作者：Anup Kumar Misra、Saibal Kumar Das、Nirmolendu Roy

  DOI：10.1080/00397919808006846

  日期：1998.4

  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.