α-D-glycero-D-gluco-7-deoxy-heptopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-glycero-D-gluco-7-deoxy-heptopyranose
• 英文别名: 7-deoxy-alpha-L-glycero-D-gluco-heptopyranoside；(2S,3R,4S,5S,6R)-6-[(1R)-1-hydroxyethyl]oxane-2,3,4,5-tetrol
• 化学式: C₇H₁₄O₆
• 分子量: 194.185
• InChiKey: PZODEECXPHBZCU-KTWJAUQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  D-glucurono-3,6-lactone acetonide 在 sodium tetrahydroborate 、 camphor-10-sulfonic acid 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 29.0h， 生成 α-D-glycero-D-gluco-7-deoxy-heptopyranose
  参考文献：
  名称：

  6R-, and 6S, -6C-methylglucose from D-glucuronolactone: Efficient synthesis of a seven carbon fucose analogue: Inhibition of some enzymes of primary metabolism

  摘要：

  Syntheses of the two epimeric 6C-methylglucoses from D-glucuronolactone rely on a nonstereoselective reduction of an intermediate lactol. A highly stereoselective reduction of a silylated lactol, which is accompanied by a silyl migration, gives easy access to 6S-6C-methylglucose-a seven carbon fucose analogue-in five steps from glucuronolactone in an overall yield of 40%. An azido analogue of 6R-6C-methylglucose is also reported. Such compounds may provide new materials for the selective inhibition of various enzymes of primary metabolism including glucokinase, glucose-6-phosphatase, and phosphoglucomutase. X-ray crystal structures of(IS,3R,4S,5S,7R,8R)-3-methyl-7,8-O-isopropylidene-3,4,7,8-tetrahydroxy-2,6-dioxabicyclo[3,3,0]octane and 7-deoxy-1,2-5,6-di-O-isopropylidene-L-glycero-alpha-D-gluco-heptofuranose are reported. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10011-4

文献信息

• EP0593419A4
  申请人：——

  公开号：EP0593419A4

  公开（公告）日：1994-08-17
• INHIBITORS FOR GLYCOSAMINOSYL TRANSFERASE-V
  申请人：CHEMBIOMED, LTD.

  公开号：EP0593419A1

  公开（公告）日：1994-04-27
• US5032505A
  申请人：——

  公开号：US5032505A

  公开（公告）日：1991-07-16
• [EN] INHIBITORS FOR GLYCOSAMINOSYL TRANSFERASE-V
  申请人：——

  公开号：WO1990005527A1

  公开（公告）日：1990-05-31

  [FR] Des accepteurs et des inhibiteurs synthétiques de glycosaminosyl transférase-V sont décrits. Les inhibiteurs et accepteurs minimum de trisaccharide spécifiques pour le GnT-V, associé à la capacité de cellules de se transformer par métabolisme, sont utiles dans le diagnostic et le traitement d'états caractérisés par des cellules métastatiques.
  [EN] Synthetic glycosaminosyl transferase-V acceptors and inhibitors are disclosed. Minimal trisaccharide inhibitors and acceptors specific for GnT-V, which is associated with the ability of cells to metastasize are useful, in diagnosis and treatment of conditions characterized by metastatic cells.
• 6R-, and 6S, -6C-methylglucose from D-glucuronolactone: Efficient synthesis of a seven carbon fucose analogue: Inhibition of some enzymes of primary metabolism
  作者：Yves Blériot、Christian F. Masaguer、Joanne Charlwood、Bryan G Winchester、Alexandra L. Lane、Sarah Crook、David J. Watkin、George W.J. Fleet

  DOI：10.1016/s0040-4020(97)10011-4

  日期：1997.11

  Syntheses of the two epimeric 6C-methylglucoses from D-glucuronolactone rely on a nonstereoselective reduction of an intermediate lactol. A highly stereoselective reduction of a silylated lactol, which is accompanied by a silyl migration, gives easy access to 6S-6C-methylglucose-a seven carbon fucose analogue-in five steps from glucuronolactone in an overall yield of 40%. An azido analogue of 6R-6C-methylglucose is also reported. Such compounds may provide new materials for the selective inhibition of various enzymes of primary metabolism including glucokinase, glucose-6-phosphatase, and phosphoglucomutase. X-ray crystal structures of(IS,3R,4S,5S,7R,8R)-3-methyl-7,8-O-isopropylidene-3,4,7,8-tetrahydroxy-2,6-dioxabicyclo[3,3,0]octane and 7-deoxy-1,2-5,6-di-O-isopropylidene-L-glycero-alpha-D-gluco-heptofuranose are reported. (C) 1997 Elsevier Science Ltd.