phenyl 2-O-allyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside | 502181-55-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-O-allyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside
• 英文别名: allyl(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Glc(b)-SPh；(2R,3R,4S,5R,6S)-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-phenylsulfanyl-5-prop-2-enoxyoxane
• CAS: 502181-55-7
• 化学式: C₃₆H₃₈O₅S
• 分子量: 582.761
• InChiKey: ORDZNEPEVUSHPE-GJXDWMKPSA-N

物化性质

• 熔点：
  51-52 °C
• 沸点：
  693.1±55.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  42
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-allyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 在 Wilkinson's catalyst 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 phenyl 3,4,6-tri-O-benzyl-2-O-(prop-1-enyl)-1-thio-β-D-glucopyranoside 、 phenyl 3,4,6-tri-O-benzyl-2-O-(prop-1-enyl)-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Allyl protecting group mediated intramolecular aglycon delivery: optimisation of mixed acetal formation and mechanistic investigation

  摘要：

  An efficient protocol for the formation of alpha-iodo mixed acetals, the first step of allyl-mediated 1AD, by reaction of allyl-derived enol ethers and alcohols, using I-2, AgOTf and di-tert-butyl methylpyridine as a novel source of I+, is reported. This reagent combination is capable of tethering glycosyl donors to the secondary alcohol groups of a variety of glycosyl acceptors including mono-, di- and trisaccharides. Mechanistic studies confirm the intramolecular nature of the glycosylation reaction, whilst the attempted use of diol glycosyl acceptors reveals limitations of both regio- and stereo selectivity in the glycosylation step. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.09.003
• 作为产物：
  描述：

  phenyl 3,4,6-tri-O-benzyl-2-O-acetyl-1-thio-β-D-glucopyranoside 在 sodium methylate 、 sodium hydride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 phenyl 2-O-allyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Total synthesis of the Glc3Man N-glycan tetrasaccharide

  摘要：

  The total synthesis of the tetrasaccharide Glcalpha(1-->2)Glcalpha(1-->3)Glcalpha(1-->3)ManalphaOMe, which corresponds to the terminal tetrasaccharide portion of the glucose terminated arm of the N-glycan tetradecasaccharide, was achieved by the use of differentially protected selenoglycosides and thioglycosides as glycosyl donors, all of which possessed non-participating protection of the 2-hydroxyl group. Favourable anomeric stereoselectivity was achieved for the glycosylation reactions by the use of ether as solvent, or co-solvent. Global deprotection by catalytic hydrogenation with palladium acetate in a mixture of ethanol and acetic acid yielded the target tetrasaccharide. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(02)01221-8

文献信息

• Total synthesis of the Glc3Man N-glycan tetrasaccharide
  作者：S.C Ennis、I Cumpstey、A.J Fairbanks、T.D Butters、M Mackeen、M.R Wormald

  DOI：10.1016/s0040-4020(02)01221-8

  日期：2002.11

  The total synthesis of the tetrasaccharide Glcalpha(1-->2)Glcalpha(1-->3)Glcalpha(1-->3)ManalphaOMe, which corresponds to the terminal tetrasaccharide portion of the glucose terminated arm of the N-glycan tetradecasaccharide, was achieved by the use of differentially protected selenoglycosides and thioglycosides as glycosyl donors, all of which possessed non-participating protection of the 2-hydroxyl group. Favourable anomeric stereoselectivity was achieved for the glycosylation reactions by the use of ether as solvent, or co-solvent. Global deprotection by catalytic hydrogenation with palladium acetate in a mixture of ethanol and acetic acid yielded the target tetrasaccharide. (C) 2002 Published by Elsevier Science Ltd.
• Allyl protecting group mediated intramolecular aglycon delivery: optimisation of mixed acetal formation and mechanistic investigation
  作者：Ian Cumpstey、Kampanart Chayajarus、Antony J. Fairbanks、Alison J. Redgrave、Christopher M.P. Seward

  DOI：10.1016/j.tetasy.2004.09.003

  日期：2004.10

  An efficient protocol for the formation of alpha-iodo mixed acetals, the first step of allyl-mediated 1AD, by reaction of allyl-derived enol ethers and alcohols, using I-2, AgOTf and di-tert-butyl methylpyridine as a novel source of I+, is reported. This reagent combination is capable of tethering glycosyl donors to the secondary alcohol groups of a variety of glycosyl acceptors including mono-, di- and trisaccharides. Mechanistic studies confirm the intramolecular nature of the glycosylation reaction, whilst the attempted use of diol glycosyl acceptors reveals limitations of both regio- and stereo selectivity in the glycosylation step. (C) 2004 Elsevier Ltd. All rights reserved.