methyl 2,3,4-tri-O-acetyl-6-O-nitro-α-D-glucopyranoside | 10300-92-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2,3,4-tri-O-acetyl-6-O-nitro-α-D-glucopyranoside
• 英文别名: Methyl-2,3,4-tri-O-acetyl-6-O-nitro-α-D-glucopyranosid；α-Methyl-D-glucosid-triacetat-(2,3,4)-nitrat-(6)；2,3,4-Tri-O-acetyl-6-O-nitro-α-methylglucosid；methyl-(O²,O³,O⁴-triacetyl-O⁶-nitro-α-D-glucopyranoside)；Methyl-(O²,O³,O⁴-triacetyl-O⁶-nitro-α-D-glucopyranosid)；methyl 2,3,4-tri-O-acetyl-6-O-nitro-alpha-d-glucopyranoside；[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-6-methoxy-2-(nitrooxymethyl)oxan-3-yl] acetate
• CAS: 10300-92-2
• 化学式: C₁₃H₁₉NO₁₁
• 分子量: 365.294
• InChiKey: MZRWYAINLIACPP-LBELIVKGSA-N

物化性质

• 熔点：
  112-113 °C
• 沸点：
  419.4±45.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-6-O-nitro-α-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 生成 methyl-3,6-anhydro-α-D-glucopyranoside
  参考文献：
  名称：

  The Formation of Anhydro Derivatives by the Action of Alkali upon Some Mononitrate-acetates of Glucose and Methylglucoside

  摘要：

  DOI：

  10.1021/ja01229a022
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 silver nitrate 、 乙腈 作用下， 生成 methyl 2,3,4-tri-O-acetyl-6-O-nitro-α-D-glucopyranoside
  参考文献：
  名称：

  103.硝酸糖。第四部分 硝酸盐和磺酸盐与甲醇钠在甲醇和某些钠盐中的反应

  摘要：

  DOI：

  10.1039/jr9580000537

文献信息

• Sugar nitrates. Part II. The preparation and reactions of some nitrates, sulphonates, sulphinates, and other esters of methyl 4 : 6-O-benzylidene-α-<scp>D</scp>-glucoside
  作者：John Honeyman、J. W. W. Morgan

  DOI：10.1039/jr9550003660

  日期：——
• X-ray and NMR studies on the rotational isomerism about the C(5)-C(6) bond of 6-substituted methyl 2,3,4,-tri-O-acetyl-6-X-α-D-glucopyranoside derivatives
  作者：D. Mentzafos、M. Polissiou、I. Grapsas、A. Hountas、M. Georgiadis、A. Terzis

  DOI：10.1007/bf01666100

  日期：1995.4

  The rotamers about the C(5)-C(6) bond of a series of 2,3,4-tri-O-acetyl-6-X-alpha-D-glucopyranozide derivatives resulting by substitution at C(6) or O(6) have been studied with H-1-NMR spectroscopy (400 MHz) and X-ray structure analysis. The methyl 2,3,4-tri-O-acetyl-6-O-triphenyl-methyl-alpha-D-glucopyranoside and the N-(1-O-methyl-2,3,4-tri-O-acetyl-alpha-D-glucopyranose-6-yl)- pyridinium nitrate crystallize in the P2(1) space group with a = 14.940(1), b = 11.232(1), c = 9.0773(7), and beta = 94.480(7) and a = 7.670(1), b = 15.384(3), c = 9.624(1) and beta = 104.90(1), respectively; the methyl 2,3,4-tri-O-acetyl-6-O-nitro-alpha-D-glucopyranoside and methyl 2,3,4-tri-O-acetyl-6-O-deoxy-6-iodo-alpha-D-glucopyrano-side crystallize in the P2(1)2(1)2(1) space group with a = 5.630(1), b = 14.360(1) and c = 22.388(3), and a = 5.556(1), b = 14.303(6) and c = 21.963(6), respectively.
• 2,3,4-Triacetyl-α-methylglucopyranoside-6-nitrate and 3,4,6-Triacetyl-β-methylglucopy-ranoside-2-nitrate
  作者：E. K. Gladding、C. B. Purves

  DOI：10.1021/ja01229a501

  日期：1944.1