methyl 3-azido-2,3-dideoxy-α-D-ribo-hexopyranoside | 188349-23-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-azido-2,3-dideoxy-α-D-ribo-hexopyranoside
• 英文别名: (2R,3S,4S,6S)-4-azido-2-(hydroxymethyl)-6-methoxyoxan-3-ol
• CAS: 188349-23-7
• 化学式: C₇H₁₃N₃O₄
• 分子量: 203.198
• InChiKey: FLZWXHAJKPSXOG-VZFHVOOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 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：
  73.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 3-azido-2,3-dideoxy-α-D-ribo-hexopyranoside 在 吡啶 、 sodium iodide 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 48.5h， 生成 methyl 4-O-acetyl-3-azido-6-iodo-2,3,6-trideoxy-α-D-ribo-hexopyranoside
  参考文献：
  名称：

  From Tri‐O‐Acetyl‐D‐Glucal to (2R,3R,5R)‐2,3‐Diazido‐5‐Hydroxycyclohexanone Oxime

  摘要：

  Methyl 3-azido-2,3-dideoxy-alpha/beta-D-arabino- and -alpha/beta-D-ribo-hexopyranosides were transformed into 6-iodo analogues via p-tolylsulfonyl compounds. Elimination of hydrogen iodide from 6-iodo glycosides provided methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-alpha- and -beta-D-threo-hex-5-eno-pyranosides or 3-azido-4-O-p-tolylsulfonyl-2,3,6-trideoxy-alpha-D-threo- and -beta-D-erythro-hex-5-eno-pyranosides. Ferrier's carbocyclization of 4-O-acetyl-3-azido-2,3,6-trideoxy-alpha- and -beta-D-threo-hex-5-eno-pyranosides gave (2S,3R,5R)-2-acetoxy-3-azido-5-hydroxycyclohcxanone, which was converted into oxime. The 2-OAc group in oxime was substituted by azide ion to yield (2R,3R,5R)-2,3-diazido-5-hydroxycyclohexanone oxime. The configuration and conformation of all products are widely discussed on the basis of the H-1 and C-13 NMR.

  DOI：

  10.1081/car-200040117
• 作为产物：
  描述：

  ((2R,3S)-3-acetoxy-6-hydroxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate 在 吡啶 、 甲醇 、 sodium azide 、 K₁₀ montmorillonite 、 sodium methylate 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 、 苯 为溶剂， 反应 78.0h， 生成 methyl 3-azido-2,3-dideoxy-α-D-ribo-hexopyranoside
  参考文献：
  名称：

  Synthesis of 6-Hydroxy-L-Daunosamine and L-Daunosamine Derivatives

  摘要：

  Methyl 3-trifluoroacetamido-2,3-dideoxy-alpha-L-lyxo-hexopyranoside (19) has been synthesized from D-glucose derivatives following two pathways. The first one involving 1,2:5,6-di-O-isopropylidene-alpha-D-glucopyranose as starting material is mainly based upon azidation at C-3, inversion of configuration at C-5 and then radical deoxygenation at C-2 (13 steps and 10% overall yield). This pathway also afforded methyl N-trifluoroacetyl-alpha-L-daunosamine 22. The second pathway, which started from tri-O-acetyl-D-glucal, relied essentially upon Michael addition of N3H on the corresponding hex-2-enose and glycosidation of the two pivaloyl compounds 33 and 34. After the beta-D-ribo isomer 34 was subsequently converted into its beta-methyl glycoside 28b, inversion of configuration at C-5 was carried out via the formation of the 6-bromo-sugar 36, followed by formation of the hex-5-enopyranoside 37. Hydroboration of 37 stereoselectively afforded 38, followed by catalytic hydrogenation and trifluoroacetylation to give 19.

  DOI：

  10.1080/07328309708006508

文献信息

• The use of tri-O-acetyl-d-glucal and -d-galactal in the synthesis of 3-acetamido-2,3-dideoxyhexopyranoses and -hexopyranosides
  作者：Beata Liberek、Aleksandra Dąbrowska、Ryszard Frankowski、Marlena Matuszewska、Zygfryd Smiatacz

  DOI：10.1016/s0008-6215(02)00288-4

  日期：2002.11

  Addition of hydrazoic acid to alpha, beta-unsaturated aldehydes derived from tri-O-acetyl-D-glucal and -D-galactal gave 3-azido-2,3-dideoxyhexopyranoses. These were converted into 1,4,6-tri-O-acetyl-3-azido-2,3-dideoxyhexopyranoses as well as methyl and ethyl glycosides. Hydrogenation of the proamine group in 3-azido-2,3-dideoxy derivatives provided different 3-amino and 3-acetamido sugars. The configuration and conformation of all products were established on the basis of the H-1 and C-13 NMR, IR and polarimetric data. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of 6-Hydroxy-L-Daunosamine and L-Daunosamine Derivatives
  作者：Laurent Daley、Pierre Roger、Claude Monneret

  DOI：10.1080/07328309708006508

  日期：1997.1.1

  Methyl 3-trifluoroacetamido-2,3-dideoxy-alpha-L-lyxo-hexopyranoside (19) has been synthesized from D-glucose derivatives following two pathways. The first one involving 1,2:5,6-di-O-isopropylidene-alpha-D-glucopyranose as starting material is mainly based upon azidation at C-3, inversion of configuration at C-5 and then radical deoxygenation at C-2 (13 steps and 10% overall yield). This pathway also afforded methyl N-trifluoroacetyl-alpha-L-daunosamine 22. The second pathway, which started from tri-O-acetyl-D-glucal, relied essentially upon Michael addition of N3H on the corresponding hex-2-enose and glycosidation of the two pivaloyl compounds 33 and 34. After the beta-D-ribo isomer 34 was subsequently converted into its beta-methyl glycoside 28b, inversion of configuration at C-5 was carried out via the formation of the 6-bromo-sugar 36, followed by formation of the hex-5-enopyranoside 37. Hydroboration of 37 stereoselectively afforded 38, followed by catalytic hydrogenation and trifluoroacetylation to give 19.
• From Tri‐<i>O</i>‐Acetyl‐<scp>D</scp>‐Glucal to (2<i>R</i>,3<i>R</i>,5<i>R</i>)‐2,3‐Diazido‐5‐Hydroxycyclohexanone Oxime
  作者：Beata Liberek、Aleksandra Dąbrowska、Ryszard Frankowski、Zygfryd Smiatacz

  DOI：10.1081/car-200040117

  日期：2004.12.27

  Methyl 3-azido-2,3-dideoxy-alpha/beta-D-arabino- and -alpha/beta-D-ribo-hexopyranosides were transformed into 6-iodo analogues via p-tolylsulfonyl compounds. Elimination of hydrogen iodide from 6-iodo glycosides provided methyl 4-O-acetyl-3-azido-2,3,6-trideoxy-alpha- and -beta-D-threo-hex-5-eno-pyranosides or 3-azido-4-O-p-tolylsulfonyl-2,3,6-trideoxy-alpha-D-threo- and -beta-D-erythro-hex-5-eno-pyranosides. Ferrier's carbocyclization of 4-O-acetyl-3-azido-2,3,6-trideoxy-alpha- and -beta-D-threo-hex-5-eno-pyranosides gave (2S,3R,5R)-2-acetoxy-3-azido-5-hydroxycyclohcxanone, which was converted into oxime. The 2-OAc group in oxime was substituted by azide ion to yield (2R,3R,5R)-2,3-diazido-5-hydroxycyclohexanone oxime. The configuration and conformation of all products are widely discussed on the basis of the H-1 and C-13 NMR.