3-acetoxy-2-acetoxymethyl-2H-pyran | 136962-85-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-acetoxy-2-acetoxymethyl-2H-pyran
• 英文别名: (3-acetyloxy-2H-pyran-2-yl)methyl acetate
• CAS: 136962-85-1
• 化学式: C₁₀H₁₂O₅
• 分子量: 212.202
• InChiKey: MFIAPFZSOIUQHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  silver thiocyanate 、 1,3,4,6-四-O-乙酰基-2-脱氧-D-来苏-吡喃己糖 在 三甲基溴硅烷 作用下， 生成 3-acetoxy-2-acetoxymethyl-2H-pyran 、 3,4,6-tri-O-acetyl-2-deoxy-β-D-lyxohexopyranosyl isothiocyanate 、 3,4,6-tri-O-acetyl-2-deoxy-α-D-lyxohexopyranosyl isothiocyanate
  参考文献：
  名称：

  Preparation and properties of 2-deoxyglycosyl isothiocyanates

  摘要：

  The syntheses of 3,4,6-tri-O-acetyl-2- deoxy-alpha and beta-D-arabino (D-lyxo)hexopyranosyl isothiocyanates (2, 3, 6, 7) and 4,6-di-O-acetyl-3-bromo-2,3-dideoxy-beta-D-arabinohexopyranosyl isothiocyanate (5) are reported. Treatments of 2,3,6, and 7 with phenacylamine hydrochloride and of 2 with aminoacetone hydrochloride gave the corresponding N-phenacyl (acetylmethyl)-N'-(2-deoxyglycosyl)-thioureas (8-12). The N-nucleoside analogues 5-methyl-1-(3',4',6'-tri-O- acetyl-2'-deoxy-alpha-D-arabinohexopyranosyl)-4-imidazoline-2-thione (13) was obtained by cyclodehydration of the thiourea 12.

  DOI：

  10.1016/s0040-4020(01)86530-3

文献信息

• Synthesis of deoxy derivatives of the glucosinolates glucotropaeolin and glucobrassicin
  作者：Harald Streicher、Laurent Latxague、Torsten Wiemann、Patrick Rollin、Joachim Thiem

  DOI：10.1016/0008-6215(95)00265-0

  日期：1995.12

  phenylacetohydroximoyl chloride or indol-3-ylacetohydroximoyl chloride, respectively. Sulfation and subsequent deprotection yielded the corresponding deoxy derivatives of glucotropaeolin and glucobrassicin, two major representatives of the glucosinolate family.

  摘要3,4,6-三-O-乙酰基-2-脱氧-1-硫代-d-阿拉伯糖基六吡喃糖，2,4,6-三-O-乙酰基-3-脱氧-1-硫代-戊糖β-d-核糖-六吡喃糖，2,3,6-三-O-苯甲酰基-4-脱氧-1-硫代-β-d-木糖-六吡喃糖和2,3,4-三-O-乙酰基-6报道了-脱氧-1-硫代-β-d-吡喃葡萄糖。这些硫醇分别与苯基乙酰基羟肟基氯或吲哚-3-基乙酰基羟肟基氯偶联。硫酸化和随后的脱保护得到了葡糖营养素和葡糖溴素的相应脱氧衍生物，这是芥子油苷家族的两个主要代表。
• Preparation and properties of 2-deoxyglycosyl isothiocyanates
  作者：José Fuentes、M.Angeles Pradera、Inmaculada Robina

  DOI：10.1016/s0040-4020(01)86530-3

  日期：1991.7

  The syntheses of 3,4,6-tri-O-acetyl-2- deoxy-alpha and beta-D-arabino (D-lyxo)hexopyranosyl isothiocyanates (2, 3, 6, 7) and 4,6-di-O-acetyl-3-bromo-2,3-dideoxy-beta-D-arabinohexopyranosyl isothiocyanate (5) are reported. Treatments of 2,3,6, and 7 with phenacylamine hydrochloride and of 2 with aminoacetone hydrochloride gave the corresponding N-phenacyl (acetylmethyl)-N'-(2-deoxyglycosyl)-thioureas (8-12). The N-nucleoside analogues 5-methyl-1-(3',4',6'-tri-O- acetyl-2'-deoxy-alpha-D-arabinohexopyranosyl)-4-imidazoline-2-thione (13) was obtained by cyclodehydration of the thiourea 12.