2-O-acetyl-1,6:3,4-dianhydro-β-D-galactopyranose | 33159-54-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧环庚烷
• 英文名称: 2-O-acetyl-1,6:3,4-dianhydro-β-D-galactopyranose
• 英文别名: 1,6:3,4-Dianhydro-2-O-acetyl-beta-d-galactopyranose；[(1R,2S,4S,5R,6R)-3,7,9-trioxatricyclo[4.2.1.02,4]nonan-5-yl] acetate
• CAS: 33159-54-5
• 化学式: C₈H₁₀O₅
• 分子量: 186.164
• InChiKey: JVBICOCAMPYKMA-DWOUCZDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-O-acetyl-1,6:3,4-dianhydro-β-D-galactopyranose 生成 1,6-anhydro-4-deoxy-4-<(1R,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-enyl>amino-β-D-glucose
  参考文献：
  名称：

  有效的α-葡萄糖苷酶抑制剂的合成：由1,6-脱水-β-D-吡喃葡萄糖残基组成的甲基胭脂红素类似物

  摘要：

  已显示化合物3a对α-葡萄糖苷酶的抑制活性比甲基Acarviosin 1强。

  DOI：

  10.1039/c39900001387

文献信息

• Synthesis of carbasugar-containing non-glycosidically linked pseudodisaccharides and higher pseudooligosaccharides
  作者：Ian Cumpstey

  DOI：10.1016/j.carres.2009.09.008

  日期：2009.11

  This minireview covers synthetic methods towards carbasugar-containing non-glycosidically linked pseudodisaccharides or higher pseudooligosaccharides. Carbocyclic pyranose mimetics (saturated or unsaturated between C-5 and C-5a) are linked by ether, thioether or amine bridges to carbohydrates or other carbasugars.

  这份简短的综述涵盖了针对含碳水化合物的非糖苷键连接的假二糖或高级假寡糖的合成方法。碳环吡喃糖模拟物（在C-5和C-5a之间饱和或不饱和）通过醚桥，硫醚桥或胺桥连接到碳水化合物或其他Carcarbugars。
• β-Acarbose. IV. Model Studies on the Alkylation of Cyclohexylamine with a Carbohydrate Epoxide
  作者：Joseph C. McAuliffe、Brian W. Skelton、Robert V. Stick、Allan H. White

  DOI：10.1071/c96154

  日期：——

  1,6:3,4-Dianhydro-2-O-benzyl-β-D-galactose has been treated with cyclohexylamine to give an amino alcohol, convertible into 2,3-di-O-acetyl-1,6-anhydro-4-cyclohexylamino-4-deoxy-β-D-glucose by reduction and acetylation. The anhydro bridge of this diacetate has been successfully opened under acetolysis conditions. The original amino alcohol has also been converted into a cyclic carbamate, a carbamate and an aziridine, by utilizing a variety of reagents and conditions. The 1,6-anhydro bridge of the cyclic carbamate, also containing a 2-O-benzyl ether, could be opened under acetolysis conditions but a comparable reaction was best done on the derived 2-O-acetyl compound. The resulting mixture of D-glucosyl acetates, still containing a cyclic carbamate, was convered into a methyl β-D-glucoside. The cyclic carbamate could be removed by hydrolysis with aqueous base to give a model glycoside for a synthesis of β-acarbose. Single-crystal X-ray structure determinations are reported for 2,3-di-O-acetyl-4-[acetyl(cyclohexyl)amino]-1,6-anhydro-4-deoxy-β-D-glucose, 1,6-anhydro-2-O-benzyl-3,4-[N-(cyclohexyl)epimino]-3,4-dideoxy-β-D-allose and methyl 2,6-di-O-acetyl-3,4-O,N-carbonyl-4-cyclohexylamino-4-deoxy-β-D-glucoside.

  1,6:3,4-二氢-2-O-苄基-β-D-半乳糖经环己基胺处理后，可转化为氨基醇。 用环己胺处理后得到氨基醇，可转化为 2,3-二-O-乙酰基-1,6-脱水-4-环己基氨基-4-脱氧-β-D-葡萄糖 通过还原和乙酰化作用。这种二乙酸酯的脱水桥在乙醇分解条件下已成功打开。 在乙酰分解条件下成功打开。原来的氨基醇 还被转化为环氨基甲酸酯、氨基甲酸酯和氮丙啶、 利用各种试剂和条件。环氨基甲酸酯的 1,6-anhydro 环状氨基甲酸酯的 1,6-脱水桥也含有 2-O-苄基醚。 醚的环状氨基甲酸酯的 1,6-脱水桥可在乙醇分解条件下打开，但类似的反应 但在衍生的 2-O-乙酰基化合物上进行类似反应的效果最好。生成的 生成的 D-葡萄糖基乙酸酯混合物仍然含有环状氨基甲酸酯、 转化成甲基 β-D-葡萄糖苷。环状氨基甲酸酯可 环氨基甲酸酯可通过水基水解去除，从而得到一个用于合成 β-乙酰基-D-葡萄糖苷的模型糖苷。 合成 β-阿拉伯糖的模型糖苷。单晶 X 射线结构测定 报告了 2,3-二-O-乙酰基-4-[乙酰基（环己基）氨基]-1,6-脱水-4-脱氧-β-D-葡萄糖、 1,6-anhydro-2-O-benzyl-3,4-[N-(cyclohexyl)epimino]-3,4-dideoxy-β-D-allose 和甲基 2,6-二-O-乙酰基-3,4-O,N-羰基-4-环己基氨基-4-脱氧-β-D-葡萄糖苷。
• OGAWA, SEIICHIRO;SHIBATA, YASUSHI;KOSUGE, YASUHIRO;YASUDA, KUNINOBU;MIZUK+, J. CHEM. SOC. CHEM. COMMUN.,(1990) N0, C. 1387-1388
  作者：OGAWA, SEIICHIRO、SHIBATA, YASUSHI、KOSUGE, YASUHIRO、YASUDA, KUNINOBU、MIZUK+

  DOI：——

  日期：——
• Synthesis of potent α-glucosidase inhibitors: methyl acarviosin analogue composed of 1,6-anhydro-β-<scp>D</scp>-glucopyranose residue
  作者：Seiichiro Ogawa、Yasushi Shibata、Yasuhiro Kosuge、Kuninobu Yasuda、Toshimi Mizukoshi、Chikara Uchida

  DOI：10.1039/c39900001387

  日期：——

  Compound 3a has been shown to possess stronger inhibitory activity against α-glucosidase than methyl acarviosin 1.

  已显示化合物3a对α-葡萄糖苷酶的抑制活性比甲基Acarviosin 1强。