7-deoxy-1,2:3,5-di-O-isopropylidene-L-glycero-α-D-gluco-heptofuranose | 197779-10-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-deoxy-1,2:3,5-di-O-isopropylidene-L-glycero-α-D-gluco-heptofuranose
• 英文别名: (1S)-1-[(1S,2R,6R,8R,9R)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecan-9-yl]ethanol
• CAS: 197779-10-5
• 化学式: C₁₃H₂₂O₆
• 分子量: 274.314
• InChiKey: GHKYOHBGSSLNII-OVHRRVLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  66.4
• 氢给体数：
  1
• 氢受体数：
  6

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	tert-Butyl-dimethyl-[(S)-1-((3aR,3bS,7S,7aS,8aR)-2,2,5,5-tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxin-7-yl)-ethoxy]-silane	183377-82-4	C19H36O6Si	388.577
  ——	(3aR,5S,6S,6aR)-5-[(1S,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-propyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol	183377-81-3	C16H32O6Si	348.512

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	6,7-dideoxy-1,2:3,5-di-O-isopropylidene-6-C-methyl-α-D-gluco-hept-6-enofuranose	257613-55-1	C14H22O5	270.326
  ——	Methanesulfonic acid (S)-1-((3aR,3bS,7S,7aS,8aR)-2,2,5,5-tetramethyl-tetrahydro-[1,3]dioxolo[4,5]furo[3,2-d][1,3]dioxin-7-yl)-ethyl ester	197779-11-6	C14H24O8S	352.406

反应信息

• 作为反应物：
  描述：

  7-deoxy-1,2:3,5-di-O-isopropylidene-L-glycero-α-D-gluco-heptofuranose 在 吡啶 、 4-二甲氨基吡啶 、 sodium azide 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 102.0h， 生成 (2R,3R,4S,5S,6R)-6-((R)-1-Azido-ethyl)-tetrahydro-pyran-2,3,4,5-tetraol
  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
• 作为产物：
  描述：

  (3aR,5S,6S,6aR)-5-[(1S,2S)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-propyl]-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-ol 在 camphor-10-sulfonic acid 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 28.0h， 生成 7-deoxy-1,2:3,5-di-O-isopropylidene-L-glycero-α-D-gluco-heptofuranose
  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

• UDP-Glucose Analogues as Inhibitors and Mechanistic Probes of UDP-Glucose Dehydrogenase
  作者：Robert E. Campbell、Martin E. Tanner

  DOI：10.1021/jo991092h

  日期：1999.12.1

  UDP-glucose dehydrogenase catalyzes the NAD(+)-dependent 2-fold oxidation of UDP-glucose to give UDP-glucuronic acid. The putative aldehyde intermediate is not released from the active site and is presumably tightly bound. We have prepared UDP-7-deoxy-alpha-D-gluco-hept-6-ulopyranose 5, that contains a methyl ketone at C-6 and cannot be further oxidized by the enzyme. Ketone 5 was found to be a competitive inhibitor of the dehydrogenase from Streptococcus pyogenes with a K-I value of 6.7 mu M. We have also prepared the secondary alcohols UDP-6S-6C-methylglucose, 4a, and UDP-6R-6C-methylglucose, 4b. Compound 4a, but not 4b, was found to be a slow substrate for the dehydrogenase and was converted into the ketone inhibitor 5. This is consistent with the notion that the pro-R hydride is transferred in the first oxidation step of the normal enzymatic reaction.
• 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.