3-acetamido-3-deoxy-2,4,6-tri-O-methyl-D-altrono-1,5-lactone | 312714-55-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetamido-3-deoxy-2,4,6-tri-O-methyl-D-altrono-1,5-lactone
• 英文别名: N-[(2R,3S,4R,5S)-3,5-dimethoxy-2-(methoxymethyl)-6-oxooxan-4-yl]acetamide
• CAS: 312714-55-9
• 化学式: C₁₁H₁₉NO₆
• 分子量: 261.275
• InChiKey: PIVANGWJMPGHCK-KYXWUPHJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-acetamido-3-deoxy-2,4,6-tri-O-methyl-D-altrono-1,5-lactone 在 盐酸 、 氢氧化钾 、 18-冠醚-6 、 碳酸氢钠 、 甲基磺酰氯 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 31.0h， 生成 (3S,4R)-3-methoxy-4-(D-erythro-trimethoxypropyl)azetidine-2-one
  参考文献：
  名称：

  Preparation of 3-Amino-3-Deoxy-2,4,5,6-Tetra-O-Methyl-D-Altronic Acid Hydrochloride, a Precursor in the Preparation of a Chiral β-Polyamide (Nylon 3 Analog)

  摘要：

  3-Amino-3-deoxy-2,4,5,6-tetra-O-methyl-D-altronic acid hydrochloride was prepared from methyl 3-azido-3-deoxy-4,6-O-benzylidene-alpha-D-altropyranoside in seven steps. The key intermediate in this synthesis was the 3-acetamido-3-deoxy-2,4,6-tri-Omethyl-D-altrono-1,5-lactone which could be transformed, in one step, into methyl 3-acetamido-3 -deoxy-2,4,5,6-tetra-O-methyl-D-altronate. However, attempts to open the 3-azido-3-deoxy-tri-O-methyl (or O-benzyl)-D-altrono-1,5-lactone intermediates gave a mixture of products, mostly, alpha,beta-unsaturated carbonyl compounds. The 3-amino-3-deoxy-2,4,5,6-tetra-O-methyl-D-altronic acid could be transformed into the corresponding beta-lactam, (3S,4R)-3-methoxy-4-(D-erythro-trimethoxypropyl) azetidine-2-one, which was further polymerized by anionic ring-opening polymerization giving poly[(2S,3R)-2-methoxy-3-(D-erythro-trimethoxypropyl) propanamide], a chiral nylon 3 analog.

  DOI：

  10.1080/07328300008544119
• 作为产物：
  描述：

  3-acetamido-3-deoxy-2,4,6-tri-O-methyl-α,β-D-altropyranose 在 乙酸酐 、 二甲基亚砜 作用下， 以75%的产率得到3-acetamido-3-deoxy-2,4,6-tri-O-methyl-D-altrono-1,5-lactone
  参考文献：
  名称：

  Preparation of 3-Amino-3-Deoxy-2,4,5,6-Tetra-O-Methyl-D-Altronic Acid Hydrochloride, a Precursor in the Preparation of a Chiral β-Polyamide (Nylon 3 Analog)

  摘要：

  3-Amino-3-deoxy-2,4,5,6-tetra-O-methyl-D-altronic acid hydrochloride was prepared from methyl 3-azido-3-deoxy-4,6-O-benzylidene-alpha-D-altropyranoside in seven steps. The key intermediate in this synthesis was the 3-acetamido-3-deoxy-2,4,6-tri-Omethyl-D-altrono-1,5-lactone which could be transformed, in one step, into methyl 3-acetamido-3 -deoxy-2,4,5,6-tetra-O-methyl-D-altronate. However, attempts to open the 3-azido-3-deoxy-tri-O-methyl (or O-benzyl)-D-altrono-1,5-lactone intermediates gave a mixture of products, mostly, alpha,beta-unsaturated carbonyl compounds. The 3-amino-3-deoxy-2,4,5,6-tetra-O-methyl-D-altronic acid could be transformed into the corresponding beta-lactam, (3S,4R)-3-methoxy-4-(D-erythro-trimethoxypropyl) azetidine-2-one, which was further polymerized by anionic ring-opening polymerization giving poly[(2S,3R)-2-methoxy-3-(D-erythro-trimethoxypropyl) propanamide], a chiral nylon 3 analog.

  DOI：

  10.1080/07328300008544119

文献信息

• Preparation of 3-Amino-3-Deoxy-2,4,5,6-Tetra-<i>O</i>-Methyl-D-Altronic Acid Hydrochloride, a Precursor in the Preparation of a Chiral β-Polyamide (Nylon 3 Analog)
  作者：María de Gracia García-Martín、María Violante de Paz Báñez、Juan A. Galbis

  DOI：10.1080/07328300008544119

  日期：2000.1

  3-Amino-3-deoxy-2,4,5,6-tetra-O-methyl-D-altronic acid hydrochloride was prepared from methyl 3-azido-3-deoxy-4,6-O-benzylidene-alpha-D-altropyranoside in seven steps. The key intermediate in this synthesis was the 3-acetamido-3-deoxy-2,4,6-tri-Omethyl-D-altrono-1,5-lactone which could be transformed, in one step, into methyl 3-acetamido-3 -deoxy-2,4,5,6-tetra-O-methyl-D-altronate. However, attempts to open the 3-azido-3-deoxy-tri-O-methyl (or O-benzyl)-D-altrono-1,5-lactone intermediates gave a mixture of products, mostly, alpha,beta-unsaturated carbonyl compounds. The 3-amino-3-deoxy-2,4,5,6-tetra-O-methyl-D-altronic acid could be transformed into the corresponding beta-lactam, (3S,4R)-3-methoxy-4-(D-erythro-trimethoxypropyl) azetidine-2-one, which was further polymerized by anionic ring-opening polymerization giving poly[(2S,3R)-2-methoxy-3-(D-erythro-trimethoxypropyl) propanamide], a chiral nylon 3 analog.