methyl 2,3-di-O-benzyl-6-O-[(tert-butyl)dimethylsilyl]-α-D-galactopyranoside | 118545-12-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3-di-O-benzyl-6-O-[(tert-butyl)dimethylsilyl]-α-D-galactopyranoside
• 英文别名: (2R,3S,4S,5R,6S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-6-methoxy-4,5-bis(phenylmethoxy)oxan-3-ol
• CAS: 118545-12-3
• 化学式: C₂₇H₄₀O₆Si
• 分子量: 488.697
• InChiKey: AEYPGYBPBJVRON-CAKRBILKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.91
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-6-O-[(tert-butyl)dimethylsilyl]-α-D-galactopyranoside 生成 methyl 2,3-di-O-benzyl-6-O-(tert-butyldimethylsilyl)-4-O-trimethylsilyl-α-D-galactopyranoside
  参考文献：
  名称：

  HASHIMOTO, HIRONOBU;HIRUMA, KAZUMI;TAMURA, JUN-ICHI, CARBOHYDR. RES., 177,(1988) C9-C12

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 2,3-di-O-benzyl-α-D-galactopyranoside 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 methyl 2,3-di-O-benzyl-6-O-[(tert-butyl)dimethylsilyl]-α-D-galactopyranoside
  参考文献：
  名称：

  一种高效合成六吡喃糖苷丙酮酸缩醛的新方法

  摘要：

  乙缩醛制备了二-O-苄基-2,3 O-甲基-1六吡喃糖苷（甘露糖，葡萄糖等）的部分和丙酮基丙酮酸或苄基丙烯酰胺的甲硅烷基化反应

  DOI：

  10.1016/0008-6215(88)85070-5

文献信息

• Synthesis and Reactions of 1,4-Anhydrogalactopyranose and 1,4-Anhydroarabinose - Steric and Electronic Limitations
  作者：Toshiki Nokami、Daniel B. Werz、Peter H. Seeberger

  DOI：10.1002/hlca.200590224

  日期：2005.11

  Scope and limitations of 1,4-anhydro sugars as precursors of glycofuranosyl building blocks are described. The experiments revealed that the choice of the substituents is very important for an efficient preparation as well as a successful ring-opening reaction of 1,4-anhydro sugars. DFT Calculations suggest that selective protonation of 1,4-anhydro sugars is the key to the selective ring opening in

  描述了1，4-脱水糖作为呋喃呋喃糖基结构单元前体的范围和局限性。实验表明，取代基的选择对于有效制备以及成功地进行1,4-脱水糖的开环反应非常重要。DFT计算表明，1,4-脱水糖的选择性质子化是仅提供呋喃糖苷的选择性开环的关键。
• Convenient synthesis of pyruvate acetals of carbohydrates by coupling of trialkylsilylated diols and pyruvates
  作者：Kazumi Hiruma、Jun-ichi Tamura、Sigeomi Horito、Juji Yoshimura、Hironobu Hashimoto

  DOI：10.1016/s0040-4020(01)89567-3

  日期：1994.1

  Hexopyranoside diols, mainly 4,6-diols with alpha-gluco, beta-gluco, alpha-galacto, beta-galacto, and alpha-manno configurations could be converted effectively (40 - 74% yields), to the corresponding pyruvate acetals by the coupling of the O-trialkylsilylated, namely, O-TBDMS and/or O-TMS diols, and ethyl pyruvate in the presence of TMSOTf at temperatures between -30 degrees C and +3 degrees C. In the case of the beta-manno isomer, the anomerization of the beta-glycoside to the alpha-glycoside as well as the ring contraction of the pyranoside to the furanoside predominated.