methyl 3-O-benzoyl-6-O-[(tert-butyl)diphenylsilyl]-α-D-mannopyranoside | 178885-10-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-benzoyl-6-O-[(tert-butyl)diphenylsilyl]-α-D-mannopyranoside
• 英文别名: Bz(-3)[TBDPS(-6)]a-Man1Me；[(2R,3R,4S,5S,6S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-3,5-dihydroxy-6-methoxyoxan-4-yl] benzoate
• CAS: 178885-10-4
• 化学式: C₃₀H₃₆O₇Si
• 分子量: 536.697
• InChiKey: JHUNCJYGICTEJX-GVGNIZHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 3-O-benzoyl-6-O-[(tert-butyl)diphenylsilyl]-α-D-mannopyranoside 在 草酰氯 、 氢氟酸 、 sodium methylate 、 sodium acetate 、 mercury(II) trifluoroacetate 、 phosphorus pentoxide 、 三乙酰氧基硼氢化钠 、 potassium carbonate 、 三乙胺 、 sodium chloride 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 水 、 溶剂黄146 、 二甲基亚砜 、 丙酮 、 乙腈 为溶剂， 反应 4.0h， 生成 Benzoic acid (2R,3S,5S,6R)-3,4,5-trihydroxy-2,6-bis-methoxymethoxy-cyclohexyl ester
  参考文献：
  名称：

  Synthesis of L-chiro-inositol-1,2,3-trisphosphate and -1,2,3,5-tetrakisphosphate by ferrier reaction of methyl α-D-mannopyranoside

  摘要：

  The Ferrier rearrangement of a methyl alpha-D-mannopyranoside derivative (8a), followed by a stereoselective reduction gave a L-chiro-inositol derivative (2), which was converted to L-chiro-inositol 1,2,3-trisphosphate (3) and L-chiro-inositol 1,2,3,5-tetrakisphosphate (4). Compounds 3 and 4 may be considered to be the C3-position stereoisomers of D-myo-inositol 1,2,6-trisphosphate (alpha-trinositol) and D-myo-inositol 1,3,4,5-tetrakisphosphate, respectively, and should be useful for the binding studies with their macromolecular counterparts. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00252-1
• 作为产物：
  描述：

  甲基-D-丙噻 以 吡啶 、 二氯甲烷 为溶剂， 生成 methyl 3-O-benzoyl-6-O-[(tert-butyl)diphenylsilyl]-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of L-chiro-inositol-1,2,3-trisphosphate and -1,2,3,5-tetrakisphosphate by ferrier reaction of methyl α-D-mannopyranoside

  摘要：

  The Ferrier rearrangement of a methyl alpha-D-mannopyranoside derivative (8a), followed by a stereoselective reduction gave a L-chiro-inositol derivative (2), which was converted to L-chiro-inositol 1,2,3-trisphosphate (3) and L-chiro-inositol 1,2,3,5-tetrakisphosphate (4). Compounds 3 and 4 may be considered to be the C3-position stereoisomers of D-myo-inositol 1,2,6-trisphosphate (alpha-trinositol) and D-myo-inositol 1,3,4,5-tetrakisphosphate, respectively, and should be useful for the binding studies with their macromolecular counterparts. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00252-1

文献信息

• Regioselective Benzoylation of 6-O-Protected and 4,6-O-Diprotected Hexopyranosides as Promoted by Chiral and Achiral Ditertiary 1,2-Diamines
  作者：Guixian Hu、Andrea Vasella

  DOI：10.1002/hlca.200290018

  日期：2002.12

  Monobenzoylation of triols (6-O-silylated glycopyranosides) or diols (4,6-O-benzylidenated glycopyranosides) with benzoyl chloride and triethylamine at −60° to 23° is promoted by catalytic amounts of ditertiary 1,2-diamines. The regioselectivity depends mostly on the structure of the alcohols; it is modulated by the configuration and constitution of the diamines, as shown by comparing the effect of Oriyama's

  三醇（6- Monobenzoylation ö -silylated glycopyranosides）或二醇（4,6- ö在-60℃至23 -benzylidenated glycopyranosides）与苯甲酰氯和三乙胺°通过催化量的二叔1,2-二胺的促进。区域选择性主要取决于醇的结构。通过比较Oriyama催化剂（（S）-1和（R）-1），N，N，N ′，N′-四甲基乙二胺（TMEDA ）的作用可以看出，它受二胺的构型和组成的调节。），N，N，N'，N'-四乙基乙二胺（TEEDA），Et 3 N和EtNMe 2。催化剂的空间位阻会削弱其对反应性的影响。与在Oriyama催化剂存在下外消旋-环己烷-1,2-二醇的单和二苯甲酰基化的适度对映选择性相一致，这些二胺对区域选择性的影响相当有限。尽管与过程简单相关，但是在某些情况下，这些催化剂比单一方法可产生更高的单种苯甲酸酯收率。在制备3-
• Study of the Regioselectivity of Intra- and Intermolecular Glycosylations of Mannoside Diol Acceptors
  作者：M. Belén Cid、Serafín Valverde、J. Cristobal López、Ana M. Gómez、Mercedes García

  DOI：10.1055/s-2005-865228

  日期：——

  The intramolecular glycosylation of thiomannoside donors linked through C6′ by a phthaloyl group to C3 of a diol mannoside acceptor is described. The unexpected results led us to undertake a systematic analysis of the factors affecting the regioselectivity of the intermolecular process. The substituents on the diol mannoside acceptor have been found to play an important role.

  描述了一种通过邻苯二甲酰基（phthaloyl group）将硫甘露苷供体的C6′连接到二醇甘露苷受体的C3位点的分子内糖苷化反应。意外的结果促使我们对影响分子间过程区域选择性的因素进行系统分析。发现二醇甘露苷受体上的取代基在这一过程中起着重要作用。
• Synthesis of L-chiro-inositol-1,2,3-trisphosphate and -1,2,3,5-tetrakisphosphate by ferrier reaction of methyl α-D-mannopyranoside
  作者：Sung-Kee Chung、Seok-Ho Yu

  DOI：10.1016/s0960-894x(96)00252-1

  日期：1996.7

  The Ferrier rearrangement of a methyl alpha-D-mannopyranoside derivative (8a), followed by a stereoselective reduction gave a L-chiro-inositol derivative (2), which was converted to L-chiro-inositol 1,2,3-trisphosphate (3) and L-chiro-inositol 1,2,3,5-tetrakisphosphate (4). Compounds 3 and 4 may be considered to be the C3-position stereoisomers of D-myo-inositol 1,2,6-trisphosphate (alpha-trinositol) and D-myo-inositol 1,3,4,5-tetrakisphosphate, respectively, and should be useful for the binding studies with their macromolecular counterparts. Copyright (C) 1996 Elsevier Science Ltd