4,6-O-benzylidene-5a-carba-β-D-glucopyranose | 504422-21-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 4,6-O-benzylidene-5a-carba-β-D-glucopyranose
• CAS: 504422-21-3
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: PNXWNQMGIVXVPJ-BUCHIQEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  19.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  79.15
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4,6-O-benzylidene-5a-carba-β-D-glucopyranose 在 Raney nickel T-4 sodium periodate 、 氢气 、 sodium methylate 、 sodium hydride 、 碳酸氢钠 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 20.0 ℃ 、250.0 kPa 条件下， 反应 58.5h， 生成 benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-5a-carba-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of an ether-linked alkyl 5a-carba-β-d-glucoside, a 5a-carba-β-d-galactoside, a 2-acetamido-2-deoxy-5a-carba-β-d-glucoside, and an alkyl 5a′-carba-β-lactoside

  摘要：

  For the purpose of providing biologically stable building blocks for the biocombinatorial synthesis using a living cell, some ether-linked alkyl 5a-carba-beta-D-glycoside primers were prepared. The key step of the synthesis was coupling of 1-bromo-n-alkanes with the 1-OH unprotected derivatives of 5a-carba-sugar analogues of D-glucose, D-galactose, and 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine). in DMF in the presence of sodium hydride. Alternatively, alkyl carba-lactoside was synthesized by incorporation of a 5a-carba-beta-D-galactose residue into the 4-position of dodecyl beta-D-glueopyranoside, A strong and specific inhibition of beta-galactosidase (K-i 0.67 muM bovine liver) was found for dodecyl 5a-carba-beta-D-galactopyranoside. (C) 2002 Elsevier Science Ltd. All rights reserved,

  DOI：

  10.1016/s0008-6215(02)00294-x
• 作为产物：
  描述：

  (1S)-2-exo,3-endo-diacetoxy-5-endo-acetoxymethyl-7-oxabicyclo<2.2.1.>heptane 在 硫酸 、 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 4,6-O-benzylidene-5a-carba-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of an ether-linked alkyl 5a-carba-β-d-glucoside, a 5a-carba-β-d-galactoside, a 2-acetamido-2-deoxy-5a-carba-β-d-glucoside, and an alkyl 5a′-carba-β-lactoside

  摘要：

  For the purpose of providing biologically stable building blocks for the biocombinatorial synthesis using a living cell, some ether-linked alkyl 5a-carba-beta-D-glycoside primers were prepared. The key step of the synthesis was coupling of 1-bromo-n-alkanes with the 1-OH unprotected derivatives of 5a-carba-sugar analogues of D-glucose, D-galactose, and 2-acetamido-2-deoxy-D-glucose (N-acetyl-D-glucosamine). in DMF in the presence of sodium hydride. Alternatively, alkyl carba-lactoside was synthesized by incorporation of a 5a-carba-beta-D-galactose residue into the 4-position of dodecyl beta-D-glueopyranoside, A strong and specific inhibition of beta-galactosidase (K-i 0.67 muM bovine liver) was found for dodecyl 5a-carba-beta-D-galactopyranoside. (C) 2002 Elsevier Science Ltd. All rights reserved,

  DOI：

  10.1016/s0008-6215(02)00294-x

文献信息

• Synthesis of 5a,5a′-dicarba-d-glucobioses from conformationally restricted carbaglucosyl triflates using SN2-type inversion with carbaglucosyl nucleophiles
  作者：Naoya Tateda、Katsumi Ajisaka、Masaji Ishiguro、Tatsuo Miyazaki

  DOI：10.1016/j.bmc.2018.12.027

  日期：2019.6

  For the synthesis of dicarba-β-d-isomaltose derivatives, the carbaglucosyl triflate locked in 4C1 conformation was synthesized by protecting with butane-2,3-diacetal group or benzylidene group. Then, 5a,5a'-dicarba-β-d-maltose and 5a,5a'-dicarba-α,β-d-trehalose were synthesized by the SN2-type inversion reaction using 4,6-O-benzylidene carbaglucosyl triflate with 4-OH and 1-OH carba-β-d-glucose derivatives

  设计了新颖的碳水化合物模拟物，其包含两个5a-carba-d-葡萄糖残基，每个残基在还原和非还原端，因此这些模拟物是5a，5a'-dicarba-d-葡萄糖生物酶。双碳二糖具有吸引人的特征，例如对内源性降解酶的稳定性，并且对糖基化反应（如美拉德反应）具有抵抗力。对于二氨基甲酸酯-β-d-异麦芽糖衍生物的合成，通过用2,3-丁烷或亚苄基保护，合成了锁定在4C1构象中的氨基甲酸氨基葡萄糖。然后，使用4,6-O-亚苄基氨基葡萄糖葡萄糖基三氟甲磺酸酯通过SN2-型转化反应合成5a，5a'-dicarba-β-d-麦芽糖和5a，5a'-dicarba-α，β-d-海藻糖。 -OH和1-OH氨基-β-d-葡萄糖衍生物，以及类似的5a，5a'