O²,O⁴-Dimethyl-3,6-anhydro-L-galactose | 120945-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: O²,O⁴-Dimethyl-3,6-anhydro-L-galactose
• 英文别名: (2S)-2-[(2R,3R,4S)-4-hydroxy-3-methoxyoxolan-2-yl]-2-methoxyacetaldehyde
• CAS: 120945-38-2
• 化学式: C₈H₁₄O₅
• 分子量: 190.196
• InChiKey: LZJXQXXTTGUCOR-OSMVPFSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  O²,O⁴-Dimethyl-3,6-anhydro-L-galactose 在 水 、 溴 作用下， 生成 O²,O⁴-dimethyl-3,6-anhydro-L-galactonic acid methyl ester
  参考文献：
  名称：

  379.关于琼脂的研究。第二部分。从琼脂中分离3：6-脱水-1-半乳糖的衍生物并合成其对映体

  摘要：

  DOI：

  10.1039/jr9390001844
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 硫酸 作用下， 生成 O²,O⁴-Dimethyl-3,6-anhydro-L-galactose
  参考文献：
  名称：

  3:6-Anhydro-l-galactose in Agar

  摘要：

  根据我们之前的沟通，我们现在能够确认，从琼脂中提取的物质（X）是3:6-脱水-l-半乳糖的衍生物，正如Hands和Peat最近提出的那样。3:6-脱水-β-甲基-d-半乳糖苷，熔点为118°C，[α]200D = -113°在水中，现在已经通过Ohle和Thiel的结晶三乙酰基6-对甲苯磺酰基α-d-半乳糖基-1-溴化物（[α]D = +157°）与碳酸银和甲醇反应后再用氢氧化钠进行去酰基化合成。对该物质进行甲基化反应定量获得结晶2:4-二甲基3:6-脱水-β-甲基-d-半乳糖苷，熔点为82°C，[α]200D = -77°在水中，-86°在氯仿中，显然是(X)的对映体，因为其性质相同但旋光性符号相反（混合熔点65°C）。我们通过制备二甲基脱水糖的苯胺衍生物进一步确认了这一点，2:4-二甲基3:6-脱水-d-半乳糖苷苯胺的熔点为118°C，而对应的琼脂衍生物的熔点为117°C，与d-苯胺混合时熔点明显降低。此外，氧化后产生的内酯的性质和稳定性与这些发现一致，因此物质（X）必须被视为2:4-二甲基3:6-脱水-β-甲基-l-半乳糖苷。

  DOI：

  10.1038/1421076a0

文献信息

• 3:6-Anhydro-l-galactose in Agar
  作者：E. G. V. PERCIVAL、I. A. FORBES

  DOI：10.1038/1421076a0

  日期：1938.12

  IN continuation of our former communication1 we are now able to confirm that the substance (X) derived from agar is a derivative of 3: 6-anhydro-l-galactose as recently advanced by Hands and Peat2. 3: 6-Anhydro-β-methyl-d-galactoside, m.p. 118°, [α]200D = −113° in water has now been synthesized from the crystalline triacetyl 6-p-toluenesulphonyl α-d-galactosyl-1-bromide ([α]D = +157°) of Ohle and Thiel3 by treatment with silver carbonate and methyl alcohol followed by deacylation with sodium hydroxide. Methylation of this substance yielded quantitatively crystalline 2: 4-dimethyl 3: 6-anhydro-β-methyl-d-galactoside, m.p. 82°, [α]200D = −77° in water, −86° in chloroform, which is undoubtedly the enantiomorph of (X), since the properties are the same but the sign of the rotation is reversed (mixed m.p. 65°). We have obtained further confirmation of this point by the preparation of the anilides of the dimethyl anhydro sugars, 2: 4-dimethyl 3: 6-anhydro-d-galactose anilide having m.p. 118°, whilst the corresponding derivative from agar had m.p. 117° strongly depressed on admixture with the d-anilide. Furthermore, the properties and stability of the lactones produced on oxidation are in agreement with these findings, so that the substance (X) must be regarded as 2: 4-dimethyl 3: 6-anhydro-β-methyl-l-galactoside.

  根据我们之前的沟通，我们现在能够确认，从琼脂中提取的物质（X）是3:6-脱水-l-半乳糖的衍生物，正如Hands和Peat最近提出的那样。3:6-脱水-β-甲基-d-半乳糖苷，熔点为118°C，[α]200D = -113°在水中，现在已经通过Ohle和Thiel的结晶三乙酰基6-对甲苯磺酰基α-d-半乳糖基-1-溴化物（[α]D = +157°）与碳酸银和甲醇反应后再用氢氧化钠进行去酰基化合成。对该物质进行甲基化反应定量获得结晶2:4-二甲基3:6-脱水-β-甲基-d-半乳糖苷，熔点为82°C，[α]200D = -77°在水中，-86°在氯仿中，显然是(X)的对映体，因为其性质相同但旋光性符号相反（混合熔点65°C）。我们通过制备二甲基脱水糖的苯胺衍生物进一步确认了这一点，2:4-二甲基3:6-脱水-d-半乳糖苷苯胺的熔点为118°C，而对应的琼脂衍生物的熔点为117°C，与d-苯胺混合时熔点明显降低。此外，氧化后产生的内酯的性质和稳定性与这些发现一致，因此物质（X）必须被视为2:4-二甲基3:6-脱水-β-甲基-l-半乳糖苷。
• Isolation of an Anhydro-Sugar Derivative from Agar
  作者：E. G. V. PERCIVAL、J. C. SOMERVILLE、I. A. FORBES

  DOI：10.1038/142797d0

  日期：1938.10

  SINCE by the kindness of Prof. W. N. Haworth We have learnt that a publication on agar is shortly to appear from the Birmingham laboratories*, we feel it desirable that one aspect of our researches on the subject should be communicated here.

  由于W.N. Haworth教授的好意，我们得知再次来自伯明翰实验室的关于琼脂的出版物即将出现，因此我们认为有必要在此传达我们在该主题上的研究之一方面。
• Isolation of an Anhydro l-Galactose Derivative from Agar
  作者：S. HANDS、S. PEAT

  DOI：10.1038/142797c0

  日期：1938.10

  IT has been found possible to methylate agar by direct treatment of the polysaccharide with methyl sulphate and sodium hydroxide solution. The product had OMe, 33.0 per cent, [α]16°D–93.1° in chloroform and it contained no sulphur.

  已经发现可以通过用硫酸甲酯和氢氧化钠溶液直接处理多糖来甲基化琼脂。该产品在氯仿中含有 33.0% 的 OMe，[α]16°D–93.1°，不含硫。
• Studies on the Chemical Constitution of Agar-agar. XVIII. Isolation of a New Crystalline Disaccharide by Enzymatic Hydrolysis of Agar-agar
  作者：Choji Araki、Kiyoshi Arai

  DOI：10.1246/bcsj.29.339

  日期：1956.3

  1. A new crystalline disaccharide has been isolated from enzymatic hydrolysates of agar. Its hexaacetate and phenylosazone have been prepared in crystalline states. 2. The name neoagarobiose has been assigned to the disaccharide isolated. 3. The structure of neoagarobiose has been shown beyond doubt to be 3-O-3′, 6′-anhydro-L-galactopyranosyl-D-galactose. It has been suggested that the glycoside linkage

  1. 从琼脂的酶解液中分离出一种新的结晶二糖。其六乙酸酯和苯唑酮已制备成结晶状态。2. 新琼脂二糖的名称已分配给分离的二糖。3. 新琼脂二糖的结构已被证实为 3-O-3', 6'-脱水-L-吡喃半乳糖基-D-半乳糖。已经表明糖苷键是α'-构型。
• Hands; Peat, Chemistry and industry, 1938, p. 937
  作者：Hands、Peat

  DOI：——

  日期：——