3-deoxy-1,2:5,6-di-O-isopropylidene-3-methoxycarbonylamino-3-C-vinyl-α-D-glucofuranose | 911122-56-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-deoxy-1,2:5,6-di-O-isopropylidene-3-methoxycarbonylamino-3-C-vinyl-α-D-glucofuranose
• 英文别名: methyl N-[(3aR,5S,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-ethenyl-2,2-dimethyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-yl]carbamate
• CAS: 911122-56-0
• 化学式: C₁₆H₂₅NO₇
• 分子量: 343.377
• InChiKey: CUWADDAAVLXQQZ-GTXQXIFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-deoxy-1,2:5,6-di-O-isopropylidene-3-methoxycarbonylamino-3-C-vinyl-α-D-glucofuranose 在 ruthenium trichloride 、 sodium chlorite 、 sodium periodate 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 水 作用下， 以 四氯化碳 、 乙腈 、 叔丁醇 为溶剂， 反应 2.25h， 生成 3-deoxy-1,2:5,6-di-O-isopropylidene-3-methoxycarbonylamino-α-D-glucofuranose 3-C-carboxylic acid
  参考文献：
  名称：

  Creation of quarternary stereocentres via [3,3]-sigmatropic rearrangement of allylic thiocyanates. A synthetic approach to (+)-myriocin

  摘要：

  A stereoselective approach to the advanced precursor of (+)-myriocin, 3-deoxy-1,2:5,6-di-O-isopropylidene-3-methoxycarbonylamino-alpha-D-glucofuranose 3-C-carboxylic acid, via the [3,3]-sigmatropic rearrangement of allylic thiocyanates prepared from D-glucose is presented. From the observed results, supported by DFT calculations, we can conclude that the [3,3]-sigmatropic rearrangement of the thiocyanato group in allylic hexofuranosides is strongly influenced by the steric interaction of the 1,2-O-isopropylidene group in the transition states. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.032
• 作为产物：
  描述：

  3-deoxy-1,2:5,6-di-O-isopropylidene-3-C-(Z)-(2-thiocyanatoethylidene)-α-D-glucofuranose 在 sodium methylate 、 2,4,6-三甲基苯甲腈N-氧化物 作用下， 以 邻二甲苯 、 乙腈 为溶剂， 反应 13.0h， 生成 3-deoxy-1,2:5,6-di-O-isopropylidene-3-methoxycarbonylamino-3-C-vinyl-α-D-glucofuranose
  参考文献：
  名称：

  Creation of quarternary stereocentres via [3,3]-sigmatropic rearrangement of allylic thiocyanates. A synthetic approach to (+)-myriocin

  摘要：

  A stereoselective approach to the advanced precursor of (+)-myriocin, 3-deoxy-1,2:5,6-di-O-isopropylidene-3-methoxycarbonylamino-alpha-D-glucofuranose 3-C-carboxylic acid, via the [3,3]-sigmatropic rearrangement of allylic thiocyanates prepared from D-glucose is presented. From the observed results, supported by DFT calculations, we can conclude that the [3,3]-sigmatropic rearrangement of the thiocyanato group in allylic hexofuranosides is strongly influenced by the steric interaction of the 1,2-O-isopropylidene group in the transition states. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.032

文献信息

• Creation of quarternary stereocentres via [3,3]-sigmatropic rearrangement of allylic thiocyanates. A synthetic approach to (+)-myriocin
  作者：Jozef Gonda、Miroslava Martinková、Jana Raschmanová、Eva Balentová

  DOI：10.1016/j.tetasy.2006.06.032

  日期：2006.7

  A stereoselective approach to the advanced precursor of (+)-myriocin, 3-deoxy-1,2:5,6-di-O-isopropylidene-3-methoxycarbonylamino-alpha-D-glucofuranose 3-C-carboxylic acid, via the [3,3]-sigmatropic rearrangement of allylic thiocyanates prepared from D-glucose is presented. From the observed results, supported by DFT calculations, we can conclude that the [3,3]-sigmatropic rearrangement of the thiocyanato group in allylic hexofuranosides is strongly influenced by the steric interaction of the 1,2-O-isopropylidene group in the transition states. (c) 2006 Elsevier Ltd. All rights reserved.