benzyl 7-O-[bis(benzyloxy)phosphoryl]-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside | 873797-13-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 7-O-[bis(benzyloxy)phosphoryl]-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside
• 英文别名: [(2R,3R)-3-[(3aS,4S,6R,6aS)-2,2-dimethyl-4-phenylmethoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-2,3-dihydroxypropyl] dibenzyl phosphate
• CAS: 873797-13-8
• 化学式: C₃₁H₃₇O₁₀P
• 分子量: 600.603
• InChiKey: HBLMAHLHGAAESM-OKXKEXSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl 7-O-[bis(benzyloxy)phosphoryl]-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside 、 三乙胺 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 17.0h， 以81%的产率得到D-glycero-α-D-manno-heptofuranose 7-phosphate triethylammonium salt
  参考文献：
  名称：

  A short synthesis of d-glycero-d-manno-heptose 7-phosphate

  摘要：

  D-glycero-D-manno-Heptopyranose 7-phosphate-an intermediate in the biosynthesis of nucleotide-activated heptoses - has been prepared in good overall yield from benzyl 5,6-dideoxy-2,3-O-isopropylidene-alpha-D-lyxo-(Z)-hept-5-enofuranoside by a short-step synthesis. Phosphitylation using the phosphoramidite procedure followed by in situ oxidation afforded the corresponding 7-O-phosphotriester derivative in high yield. Subsequent osmylation proceeded in good diastereoselectivity (4:1) to furnish the D-glycero-D-manno-configured derivative, which was separated from the L-glycero-L-gulo-isomer by chromatography. Hydrogenolysis led to simultaneous removal of the benzyl and isopropylidene groups and afforded the target compound in high yield, which serves as a substrate of bacterial heptose 7-phosphate kinases. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.10.003
• 作为产物：
  描述：

  二苯基N,N'-二异丙基亚磷酰胺 在 四氮唑 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 22.0h， 生成 benzyl 7-O-[bis(benzyloxy)phosphoryl]-2,3-O-isopropylidene-D-glycero-α-D-manno-heptofuranoside
  参考文献：
  名称：

  A short synthesis of d-glycero-d-manno-heptose 7-phosphate

  摘要：

  D-glycero-D-manno-Heptopyranose 7-phosphate-an intermediate in the biosynthesis of nucleotide-activated heptoses - has been prepared in good overall yield from benzyl 5,6-dideoxy-2,3-O-isopropylidene-alpha-D-lyxo-(Z)-hept-5-enofuranoside by a short-step synthesis. Phosphitylation using the phosphoramidite procedure followed by in situ oxidation afforded the corresponding 7-O-phosphotriester derivative in high yield. Subsequent osmylation proceeded in good diastereoselectivity (4:1) to furnish the D-glycero-D-manno-configured derivative, which was separated from the L-glycero-L-gulo-isomer by chromatography. Hydrogenolysis led to simultaneous removal of the benzyl and isopropylidene groups and afforded the target compound in high yield, which serves as a substrate of bacterial heptose 7-phosphate kinases. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2005.10.003

文献信息

• A short synthesis of d-glycero-d-manno-heptose 7-phosphate
  作者：Hacer Güzlek、Andrea Graziani、Paul Kosma

  DOI：10.1016/j.carres.2005.10.003

  日期：2005.12

  D-glycero-D-manno-Heptopyranose 7-phosphate-an intermediate in the biosynthesis of nucleotide-activated heptoses - has been prepared in good overall yield from benzyl 5,6-dideoxy-2,3-O-isopropylidene-alpha-D-lyxo-(Z)-hept-5-enofuranoside by a short-step synthesis. Phosphitylation using the phosphoramidite procedure followed by in situ oxidation afforded the corresponding 7-O-phosphotriester derivative in high yield. Subsequent osmylation proceeded in good diastereoselectivity (4:1) to furnish the D-glycero-D-manno-configured derivative, which was separated from the L-glycero-L-gulo-isomer by chromatography. Hydrogenolysis led to simultaneous removal of the benzyl and isopropylidene groups and afforded the target compound in high yield, which serves as a substrate of bacterial heptose 7-phosphate kinases. (c) 2005 Elsevier Ltd. All rights reserved.