methyl 3-O-allyl-4,6-O-benzylidene-β-D-mannopyranoside | 173829-05-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 3-O-allyl-4,6-O-benzylidene-β-D-mannopyranoside
• 英文别名: (2R,4aR,6R,7S,8R,8aR)-6-methoxy-2-phenyl-8-prop-2-enoxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-ol
• CAS: 173829-05-5
• 化学式: C₁₇H₂₂O₆
• 分子量: 322.358
• InChiKey: ASPVDBYGHHICFR-RNGXCGTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-O-allyl-4,6-O-benzylidene-β-D-mannopyranoside 在 盐酸 、 3 A molecular sieve 、 4 A molecular sieve 、 水 、 sodium acetate 、 sodium hydride 、 sodium cyanoborohydride 、 溶剂黄146 、 三氟甲烷磺酸甲酯 、 palladium dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 50.42h， 生成 methyl 2,6-di-O-benzyl-4-O-<2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranosyl>-β-D-mannopyranoside
  参考文献：
  名称：

  Misra, Anup Kumar; Roy, Nirmolendu, Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995, vol. 34, # 10, p. 865 - 868

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 3-O-allyl-4,6-O-benzylidene-β-D-glucopyranoside 在 sodium tetrahydroborate 、 乙酸酐 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 21.0h， 生成 methyl 3-O-allyl-4,6-O-benzylidene-β-D-mannopyranoside
  参考文献：
  名称：

  2型克雷伯菌的抗原四糖重复单元的合成

  摘要：

  二糖乙基2,4,6-三-O-乙酰基-3-O-（2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖基）-1-硫代-β-D-吡喃葡萄糖苷（6）和2,6-二-O-苄基-3-O-（2,3,4-三-O-苄基甲基-α-D-吡喃葡萄糖基尿酸甲酯）-β-D-甘露吡喃糖苷（21）在三氟甲磺酸甲酯的存在下进行合成和缩合，得到四糖衍生物。除去保护基，得到3-O-（甲基α-D-吡喃葡萄糖基尿酸）-4-O-（3-O-α-D-吡喃葡萄糖基-β-D-吡喃葡萄糖基）-β-D-甘露吡喃糖苷（23）， 2型克雷伯氏菌抗原的重复单元，以其甲酯甲基糖苷的形式存在。

  DOI：

  10.1016/0008-6215(95)00231-x

文献信息

• Anomalous Zemplén deacylation reactions of α- and β-d-mannopyranoside derivatives
  作者：Károly Ágoston、András Dobó、János Rákó、János Kerékgyártó、Zoltán Szurmai

  DOI：10.1016/s0008-6215(00)00283-4

  日期：2001.1

  Reaction of mono-, di-, and trisaccharide derivatives of methyl beta -D- and octyl beta -D-mannopyranosides bearing ester groups at isolated and non-isolated positions on the same molecule, under Zemplen conditions (catalytic amount of sodium methoxide in methanol) gave partially deacylated compounds, in which the O-acyl groups were retained at isolated sites. In the case of one disaccharide, all the benzoyl groups remained intact at the reducing end, while all the acetyl functions were removable from the nonreducing end. In another case, both isolated ester groups at positions 2 and 4 were retained at the reducing end. The isolated 2-O-acyl groups on methyl alpha -D-mannopyranoside compounds were more labile than on the corresponding beta -mannosides under the same conditions. The mechanism of the reaction may be different for ester groups at isolated or non-isolated positions. In the latter case, acyl migration may take place and carry acyl groups into a less hindered position. (C) 2001 Published by Elsevier Science Ltd. All rights reserved.
• Synthesis of the tetrasaccharide repeating unit of the antigen from Klebsiella type 2
  作者：Anup Kumar Misra、Nirmolendu Roy

  DOI：10.1016/0008-6215(95)00231-x

  日期：1995.11

  been synthesized and condensed in the presence of methyl triflate to afford a tetrasaccharide derivative. Removal of protecting groups gave methyl 3-O-(methyl alpha-D-glucopyranosyluronate)-4-O-(3-O-alpha-D- glucopyranosyl-beta-D-glucopyranosyl)-beta-D-mannopyranoside (23), the repeating unit of the antigen from Klebsiella type 2, in the form of its methyl ester methyl glycoside.

  二糖乙基2,4,6-三-O-乙酰基-3-O-（2,3,4,6-四-O-苄基-α-D-吡喃葡萄糖基）-1-硫代-β-D-吡喃葡萄糖苷（6）和2,6-二-O-苄基-3-O-（2,3,4-三-O-苄基甲基-α-D-吡喃葡萄糖基尿酸甲酯）-β-D-甘露吡喃糖苷（21）在三氟甲磺酸甲酯的存在下进行合成和缩合，得到四糖衍生物。除去保护基，得到3-O-（甲基α-D-吡喃葡萄糖基尿酸）-4-O-（3-O-α-D-吡喃葡萄糖基-β-D-吡喃葡萄糖基）-β-D-甘露吡喃糖苷（23）， 2型克雷伯氏菌抗原的重复单元，以其甲酯甲基糖苷的形式存在。
• Misra, Anup Kumar; Roy, Nirmolendu, Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1995, vol. 34, # 10, p. 865 - 868
  作者：Misra, Anup Kumar、Roy, Nirmolendu

  DOI：——

  日期：——