β-D-glucopyranosylmethanal | 187092-23-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-glucopyranosylmethanal
• 英文别名: (2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxane-2-carbaldehyde
• CAS: 187092-23-5
• 化学式: C₇H₁₂O₆
• 分子量: 192.169
• InChiKey: OTIVWTQFQXQFRI-PJEQPVAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  β-D-glucopyranosylmethanal 在 盐酸羟胺 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 生成 (2S,3R,4R,5S,6R)-3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-carbaldehyde oxime
  参考文献：
  名称：

  Behaviour of the Primary Nitro Group Under Denitration Conditions

  摘要：

  Treatment of per-O-acetylated or acetalated glycosylnitromethanes derived from the common hexoses and pentoses with tributyltin hydride and a catalytic amount of a radical initiator [1,1'-azobis(cyclohexanecarbonitrile)] in refluxing benzene easily afforded the corresponding glycosylmethanal oximes in 84-97% yields. Per-O-acetylated C-beta-glycopyranosylmethanal oximes were employedfor synthesis of versatile C-beta-glycopyranosyl cyanides of the beta-D-gluco, beta-D-manno, beta-D-galacto, beta-D-xylo, and beta-L-rhamno configurations.

  DOI：

  10.1080/07328300008544067
• 作为产物：
  描述：

  (1S)-1,5-脱水-1-(硝基甲基)-D-山梨糖醇 在 sodium hydroxide 、 臭氧 作用下， 以 水 为溶剂， 生成 β-D-glucopyranosylmethanal
  参考文献：
  名称：

  Synthesis of 2-(β-?-glycopyranosyl)nitroethenes and -nitroethanes via aldehydo derivatives

  摘要：

  DOI：

  10.1016/s0008-6215(96)00208-x

文献信息

• Synthesis of 2-(β-?-glycopyranosyl)nitroethenes and -nitroethanes via aldehydo derivatives
  作者：M Petrusová

  DOI：10.1016/s0008-6215(96)00208-x

  日期：1996.12.13
• VOIE COURTE DE SYNTHESE DU 1,6:2,3-DIANHYDRO-BETA-D-MANNOPYRANOSE
  申请人：SANOFI

  公开号：EP2331550B1

  公开（公告）日：2013-11-13
• Behaviour of the Primary Nitro Group Under Denitration Conditions
  作者：Duy-Phong Pham-Huu、Mária Petrušová、James N. BeMiller、Ladislav Petruš

  DOI：10.1080/07328300008544067

  日期：2000.1

  Treatment of per-O-acetylated or acetalated glycosylnitromethanes derived from the common hexoses and pentoses with tributyltin hydride and a catalytic amount of a radical initiator [1,1'-azobis(cyclohexanecarbonitrile)] in refluxing benzene easily afforded the corresponding glycosylmethanal oximes in 84-97% yields. Per-O-acetylated C-beta-glycopyranosylmethanal oximes were employedfor synthesis of versatile C-beta-glycopyranosyl cyanides of the beta-D-gluco, beta-D-manno, beta-D-galacto, beta-D-xylo, and beta-L-rhamno configurations.