methyl 3-azido-3-deoxy-α-D-altropyranoside | 20379-58-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-azido-3-deoxy-α-D-altropyranoside
• 英文别名: 3-Azido-3-deoxy-α-D-altropyranosyl-methylether；(2R,3S,4R,5S,6S)-4-azido-2-(hydroxymethyl)-6-methoxyoxane-3,5-diol
• CAS: 20379-58-2
• 化学式: C₇H₁₃N₃O₅
• 分子量: 219.197
• InChiKey: WUXIOHNNHKEPKP-OVHBTUCOSA-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：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93.5
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-3-deoxy-α-D-altropyranoside 在 盐酸 、 乙酸酐 、 sodium hydride 、 二甲基亚砜 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 145.0h， 生成 2,4,6-tri-O-benzyl-3-deoxy-D-erythro-hex-2-enonolactone
  参考文献：
  名称：

  一些3-脱氧-D-戊二酸衍生物的制备和反应性

  摘要：

  3-氨基-3-脱氧-2,4,5,6-四-O-甲基-D-丙二酸盐酸盐是制备聚[（2 S，3 R）-2-甲氧基-3]的关键中间体-（D-赤型-三甲氧基丙基）丙酰胺]，手性尼龙3类似物。现在，我们描述了该氨基酸的替代合成路线及其某些3-脱氧衍生物的出乎意料的反应性。尝试打开3-叠氮基-3-脱氧-三-O-甲基（或O-苄基）-D -altrono-1,5-内酯中间体得到产物的混合物，主要是α，β-不饱和羰基化合物。

  DOI：

  10.1081/car-100103954
• 作为产物：
  描述：

  methyl 3-azido-3-deoxy-4,6-O-benzylidene-α-D-altropyranoside 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 1.5h， 生成 methyl 3-azido-3-deoxy-α-D-altropyranoside
  参考文献：
  名称：

  Synthesis of (−)-8a-epi-Swainsonine, (1S,2R,8R,8aS)-Octahydro-1,2,8-indolizinetriol

  摘要：

  从已知的甲基 3-叠氮-4,6-O-亚苄基-3-脱氧-α-d-丙吡喃糖苷开始，合成了(-)-8a-epi-蛇床子碱(4)，它是生理上有趣的吲哚利嗪生物碱(-)-蛇床子碱(1)的立体异构体之一。将 4 的 α-d-mannosidase 抑制活性与天然 1 进行了比较。

  DOI：

  10.1246/bcsj.60.3667

文献信息

• Synthesis of (−)-8a-<i>epi</i>-Swainsonine, (1<i>S</i>,2<i>R</i>,8<i>R</i>,8a<i>S</i>)-Octahydro-1,2,8-indolizinetriol
  作者：Kin-ichi Tadano、Yukinori Hotta、Masahiro Morita、Tetsuo Suami、Bryan Winchester、Isabello Centi di Bello

  DOI：10.1246/bcsj.60.3667

  日期：1987.10

  (−)-8a-epi-Swainsonine (4), one of the stereocongeners of physiologically interesting indolizidine alkaloid (−)-swainsonine (1), has been synthesized starting from known methyl 3-azido-4,6-O-benzylidene-3-deoxy-α-d-altropyranoside. The α-d-mannosidase inhibitory activity of 4 was compared with natural 1.

  从已知的甲基 3-叠氮-4,6-O-亚苄基-3-脱氧-α-d-丙吡喃糖苷开始，合成了(-)-8a-epi-蛇床子碱(4)，它是生理上有趣的吲哚利嗪生物碱(-)-蛇床子碱(1)的立体异构体之一。将 4 的 α-d-mannosidase 抑制活性与天然 1 进行了比较。
• Synthesis of (−)-8a-<i>epi</i>-Swainsonine, (1<i>S</i>,2<i>R</i>, 8<i>R</i>, 8a<i>S</i>) -Octahydro-1,2,8-indolizinetriol
  作者：Kin-ichi Tadano、Yukinori Hotta、Masahiro Morita、Tetsuo Suami、Bryan Winchester、Isabelle Cenci di Bello

  DOI：10.1246/cl.1986.2105

  日期：1986.12.5

  The title compound, one of the stereoisomers of physiologically interesting indolizidine alkaloid swainsonine, has been synthesized from the known methyl 3-azido-4,6-O-benzylidene-3-deoxy-α-d-altropyranoside.

  标题化合物是具有生理意义的吲哚利嗪生物碱 Swainsonine 的立体异构体之一，由已知的甲基 3-叠氮-4,6-O-亚苄基-3-脱氧-α-d-丙吡喃糖苷合成。
• Fluorination of 2-hydroxy-hexopyranosides by DAST: towards formyl C-glycofuranosides from equatorial-2-OH methyl hexopyranosides
  作者：Yolanda Vera-Ayoso、Pastora Borrachero、Francisca Cabrera-Escribano、Ana T. Carmona、Manuel Gómez-Guillén

  DOI：10.1016/j.tetasy.2003.11.034

  日期：2004.2

  Reaction of diversely configured and substituted, unbranched methyl D-hexopyranosides with the DAST in dichloromethane or acetonitrile led to normal substitution products and/or rearranged fluoro compounds (ring-contracted 2,5-anhydro-1-fluoro-1-I-methylhexitol derivatives, 2-methoxy-D-hexopyranosyl fluorides, and, for some 3-azido substrates, rearranged 2-azido-3-fluoro-D-hexopyranosides). When the reaction was performed in acetonitrile, the solvent participation as a nucleophile (Ritter reaction) was observed in one case. For a 2,4-unprotected 3-azido substrate, 2,3-dehydration and fluorination at C(4), the latter with epimerization, took place. F-19/H-1 and F-19/C-13 coupling constant values were systematically applied to discriminate between isomeric structures for fluorinated products, and for some, previously described, coming from five 3-branched-chain D- or L-hexopyranosides, thus discarding the previously reported structural assignment. From the synthetic point of view, the most outstanding result was the preparation of 2,5-anhydro-1-fluoro-1-O-methylhexitols, showing a latent formyl group functionality, a transformation, which was achieved in one case. A rationalization for the formation of the different types of product is also proposed. (C) 2003 Elsevier Ltd. All rights reserved.
• PREPARATION AND REACTIVITY OF SOME 3-DEOXY-<scp>D</scp>-ALTRONIC ACID DERIVATIVES
  作者：María de Gracia García-Martín、María Violante de Paz Báñez、Juan A. Galbis

  DOI：10.1081/car-100103954

  日期：2001.3.31

  3-Amino-3-deoxy-2,4,5,6-tetra-O-methyl-D-altronic acid hydrochloride was the key intermediate in the preparation of poly[(2S,3R)-2-methoxy-3-(D-erythro-trimethoxypropyl)propanamide], a chiral nylon 3 analog. We now describe an alternative synthetic route to this amino acid and the unexpected reactivity of some of its 3-deoxy derivatives. Attempts to open the 3-azido-3-deoxy-tri-O-methyl (or O-benzyl)-D-altrono-1

  3-氨基-3-脱氧-2,4,5,6-四-O-甲基-D-丙二酸盐酸盐是制备聚[（2 S，3 R）-2-甲氧基-3]的关键中间体-（D-赤型-三甲氧基丙基）丙酰胺]，手性尼龙3类似物。现在，我们描述了该氨基酸的替代合成路线及其某些3-脱氧衍生物的出乎意料的反应性。尝试打开3-叠氮基-3-脱氧-三-O-甲基（或O-苄基）-D -altrono-1,5-内酯中间体得到产物的混合物，主要是α，β-不饱和羰基化合物。
• 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.