acetyl 5-C-(isopropyl 2-acetamido-2,6-dideoxy-3,4-O-isopropylidene-β-D-galactopyranosid-6-yl)-2,3-O-idsopropylidene-β-D-allopentofuranoside | 143996-46-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: acetyl 5-C-(isopropyl 2-acetamido-2,6-dideoxy-3,4-O-isopropylidene-β-D-galactopyranosid-6-yl)-2,3-O-idsopropylidene-β-D-allopentofuranoside
• CAS: 143996-46-7
• 化学式: C₂₄H₃₉NO₁₁
• 分子量: 517.574
• InChiKey: QUFUODMVMSVLSU-OPALZYMISA-N

反应信息

• 作为产物：
  描述：

  benzyl 5-C-(isopropyl 2-azido-2,6-dideoxy-3,4-O-isopropylidene-β-D-galactopyranosid-6-yl)-2,3-O-isopropylidene-β-D-ribopentopyranos-4-uloside 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 acetyl 5-C-(isopropyl 2-acetamido-2,6-dideoxy-3,4-O-isopropylidene-β-D-galactopyranosid-6-yl)-2,3-O-idsopropylidene-β-D-allopentofuranoside
  参考文献：
  名称：

  New convenient synthesis of tunicamine

  摘要：

  A synthesis of tunicamine, the eleven-carbon atom sugar component of tunicamycin antibiotics, was described. The synthesis started from a derivative of 2-azido-2-deoxy-D-galactose (11) which was condensed with a furfuryl alcohol moiety. Achmatowicz-type transformation of this moiety to allofuranose system yielded a derivative of tunicamine. The synthesis required 11 steps and yielded 27 in 5.4% yield (from 11) and with good stereoselectivity.

  DOI：

  10.1016/s0040-4020(01)89859-8