3-O-Benzyl-2-deoxy-5-(triphenylmethyl)-D-erythro-pentofuranoside | 105454-48-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3-O-Benzyl-2-deoxy-5-(triphenylmethyl)-D-erythro-pentofuranoside
• 英文别名: methyl 3-O-benzyl-2-deoxy-5-O-tritylribofuranoside；methyl 2-deoxy-3-benzyl-5-trityl-D-ribofuranoside；(2R,3S)-5-methoxy-3-phenylmethoxy-2-(trityloxymethyl)oxolane
• CAS: 105454-48-6
• 化学式: C₃₂H₃₂O₄
• 分子量: 480.604
• InChiKey: MNFSUOLVWYMOCP-RLZXXUCQSA-N

物化性质

• 沸点：
  588.8±50.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-O-Benzyl-2-deoxy-5-(triphenylmethyl)-D-erythro-pentofuranoside 在 吡啶 、 咪唑 、 chromium(VI) oxide 、 盐酸 、 氢氧化钾 、 ammonium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 cerium(III) chloride 、 草酰氯 、 乙酸酐 、 二甲基亚砜 、 三乙胺 、 三苯基膦 、 calcium carbonate 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 二氯甲烷 、 苯 为溶剂， 反应 118.92h， 生成 methyl 2,6-dideoxy-3-C-methyl-α-L-xylo-hexopyranoside
  参考文献：
  名称：

  Stereoselectivity of Addition of Organometallic Reagents to Pentodialdo-1,4-furanoses: Synthesis of L-Axenose and D-Evermicose from a Common Intermediate

  摘要：

  The additions of organometallic reagents to two pentodialdo-1,4-furanosides (methyl 3-O-benzyl-2-deoxy-alpha-D-erythro-pentofuranoside and its beta-anomer) were carried out under a variety of experimental conditions. Methylmagnesium halides, methyllithium, methylcerium and the organotitanium reagent MeTi(OiPr)(3) were reacted with the pentodialdo-1,4-furanosides in an effort to determine if the stereoselectivity of addition to the formyl group is the result of chelation or nonchelation control and to determine the effect of anomeric configuration. The stereochemistry of the products was assigned by NMR methods and correlation with known compounds synthesized previously. The stereoselectivity of addition depends on the configuration at the anomeric center of the dialdose, with the beta-anomer giving mainly the product of a non-chelation-controlled addition and the beta-anomer giving the opposite stereoselectivity. The major product obtained from the beta-anomer was utilized as a key intermediate in the synthesis of two branched-chain carbohydrates, axenose and evermicose, found in antibiotics. Methylcerium additions are the most efficient method for introducing the branching methyl group in a 2-deoxyfuranosid-3-ulose.

  DOI：

  10.1021/jo00106a035
• 作为产物：
  描述：

  溴甲苯 、 methyl 2-deoxy-5-O-trityl-α,β-D-erythro-pentofuranoside 在 吡啶 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 、 甲苯 为溶剂， 生成 3-O-Benzyl-2-deoxy-5-(triphenylmethyl)-D-erythro-pentofuranoside
  参考文献：
  名称：

  2-deoxyuridines and riboside precursors

  摘要：

  提供了一种制备特定2-去氧尿嘧啶的过程，包括以下步骤：形成取代烷基5-O-"保护"的2-去氧核糖苷，通过烃基化后处理该化合物，然后在路易斯或布朗斯特德酸的存在下将烃基化化合物与硅基尿嘧啶缩合形成尿嘧啶。此外，几种三苯甲基化的核糖苷也是新的化合物。

  公开号：

  US04898936A1

文献信息

• US4675390A
  申请人：——

  公开号：US4675390A

  公开（公告）日：1987-06-23
• US4898936A
  申请人：——

  公开号：US4898936A

  公开（公告）日：1990-02-06
• Stereoselectivity of Addition of Organometallic Reagents to Pentodialdo-1,4-furanoses: Synthesis of L-Axenose and D-Evermicose from a Common Intermediate
  作者：Robert M. Giuliano、Frank J. Jr. Villani

  DOI：10.1021/jo00106a035

  日期：1995.1

  The additions of organometallic reagents to two pentodialdo-1,4-furanosides (methyl 3-O-benzyl-2-deoxy-alpha-D-erythro-pentofuranoside and its beta-anomer) were carried out under a variety of experimental conditions. Methylmagnesium halides, methyllithium, methylcerium and the organotitanium reagent MeTi(OiPr)(3) were reacted with the pentodialdo-1,4-furanosides in an effort to determine if the stereoselectivity of addition to the formyl group is the result of chelation or nonchelation control and to determine the effect of anomeric configuration. The stereochemistry of the products was assigned by NMR methods and correlation with known compounds synthesized previously. The stereoselectivity of addition depends on the configuration at the anomeric center of the dialdose, with the beta-anomer giving mainly the product of a non-chelation-controlled addition and the beta-anomer giving the opposite stereoselectivity. The major product obtained from the beta-anomer was utilized as a key intermediate in the synthesis of two branched-chain carbohydrates, axenose and evermicose, found in antibiotics. Methylcerium additions are the most efficient method for introducing the branching methyl group in a 2-deoxyfuranosid-3-ulose.
• 2-deoxyuridines and riboside precursors
  申请人：PCR, Inc.

  公开号：US04898936A1

  公开（公告）日：1990-02-06

  A process is provided for the preparation of certain 2-deoxyuridines including the steps forming a substituted alkyl 5-O-"protected"-2-deoxyribofuranoside, hydrocarbylating the latter compound, and condensing the hydrocarbylated compound in the presence of a Lewis or Bronsted acid with a silyluracil to form a uridine. Several tritylated ribofuranosides are novel compounds per se.

  提供了一种制备特定2-去氧尿嘧啶的过程，包括以下步骤：形成取代烷基5-O-"保护"的2-去氧核糖苷，通过烃基化后处理该化合物，然后在路易斯或布朗斯特德酸的存在下将烃基化化合物与硅基尿嘧啶缩合形成尿嘧啶。此外，几种三苯甲基化的核糖苷也是新的化合物。