methyl 2,3,6-trideoxy-3-(O-benzylhydroxyamino)-3-C-methyl-α-L-ribo-hexopyranoside | 149353-46-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,6-trideoxy-3-(O-benzylhydroxyamino)-3-C-methyl-α-L-ribo-hexopyranoside
• 英文别名: (2S,3R,4R,6R)-6-methoxy-2,4-dimethyl-4-(phenylmethoxyamino)oxan-3-ol
• CAS: 149353-46-8
• 化学式: C₁₅H₂₃NO₄
• 分子量: 281.352
• InChiKey: GOGZXBOMBYFZTB-PMOUVXMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  60
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,3,6-trideoxy-3-(O-benzylhydroxyamino)-3-C-methyl-α-L-ribo-hexopyranoside 在 palladium on activated charcoal 氢气 、 间氯过氧苯甲酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.33h， 生成 methyl 2,3,6-trideoxy-3-C-methyl-3-nitro-α-L-ribo-hexopyranoside
  参考文献：
  名称：

  A new stereoselective route to branched-chain nitro and amino sugars: synthesis of both enantiomers of decilonitrose and avidinosamine

  摘要：

  Short, efficient, and highly diastereoselective syntheses of the title carbohydrates (15, 21, and 22), components of new anthracycline antibiotics, on a gram scale from readily available keto sugar precursors 6 and 17 are described. The syntheses feature the smooth and clean addition of organocerium compounds to benzyloxyimino derivatives 7 and 18, which provide the branched-chain hydroxyamino sugars (9,20) bearing an equatorial methyl group with complete regio- and stereocontrol. Treatment of oximino deoxy sugars (7,18) with methyllithium resulted in beta-elimination and afforded pyranoid 1-enol 3-one oximes (8, 19).

  DOI：

  10.1021/jo00066a029
• 作为产物：
  描述：

  methyl 2,6-dideoxy-α,β-L-erythro-hexopyranosid-3-ulose 在 cerium(III) chloride 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 methyl 2,3,6-trideoxy-3-(O-benzylhydroxyamino)-3-C-methyl-α-L-ribo-hexopyranoside
  参考文献：
  名称：

  A new stereoselective route to branched-chain nitro and amino sugars: synthesis of both enantiomers of decilonitrose and avidinosamine

  摘要：

  Short, efficient, and highly diastereoselective syntheses of the title carbohydrates (15, 21, and 22), components of new anthracycline antibiotics, on a gram scale from readily available keto sugar precursors 6 and 17 are described. The syntheses feature the smooth and clean addition of organocerium compounds to benzyloxyimino derivatives 7 and 18, which provide the branched-chain hydroxyamino sugars (9,20) bearing an equatorial methyl group with complete regio- and stereocontrol. Treatment of oximino deoxy sugars (7,18) with methyllithium resulted in beta-elimination and afforded pyranoid 1-enol 3-one oximes (8, 19).

  DOI：

  10.1021/jo00066a029

文献信息

• OZONE/OXONE-MEDIATED OXIDATIONS OF AMINO AND O-BENZYLHYDROXYLAMINO SUGARS
  作者：Lincoln Noecker、Robert Giuliano、Michael Cooney、Walter Boyko、Walter Zajac, Jr.

  DOI：10.1081/car-120016852

  日期：——

  A method for the preparation of C-methyl branched nitro sugars from the corresponding amino sugars by oxidation with mixed oxidants is described. Ozonolysis of the amino sugars in the presence of OXONE (potassium monopersulfate) and acetone (Bashir-Hashemi's procedure) gave nitro sugars in good yields. Oxidation of an O-benzylhydroxylamino sugar by this method resulted in deprotection and oxidation

  描述了通过用混合氧化剂氧化由相应的氨基糖制备C-甲基支链硝基糖的方法。在OXONE（单过硫酸钾）和丙酮（Bashir-Hashemi法）存在下，对氨基糖进行臭氧分解可以得到高收率的硝化糖。通过该方法氧化O-苄基羟氨基糖导致脱保护和一步氧化，直接得到硝基糖。与DMDO相比，混合氧化剂方法在实验上更简单，更方便使用，而DMDO先前已被报道用于氨基糖的氧化。