5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-decitol | 144542-40-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-decitol
• 英文别名: tert-butyl N-[(2S)-1-hydroxy-4-[(2S,3S,4R,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]butan-2-yl]carbamate
• CAS: 144542-40-5
• 化学式: C₄₃H₅₃NO₈
• 分子量: 711.896
• InChiKey: NUBMJVCGCCCTMK-DUBFBOMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.39
• 重原子数：
  52.0
• 可旋转键数：
  18.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  104.71
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-decitol 在 jones reagent 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 生成
  参考文献：
  名称：

  Carbon-linked galactosphingolipid analogs bind specifically to HIV-1 gp120

  摘要：

  DOI：

  10.1021/ja00052a072
• 作为产物：
  描述：

  (2R,3S,4R)-1,3,4-tris(benzyloxy)hex-5-en-2-ol 在 Grubbs catalyst first generation 4-二甲氨基吡啶 、 四甲基乙二胺 、 四氯化钛 、 sodium hydride 、 对甲苯磺酸 、 N,N'-二环己基碳二亚胺 、 lead(II) chloride 作用下， 以 甲醇 为溶剂， 生成 5,9-anhydro-6,7,8,10-tetra-O-benzyl-2,3,4-trideoxy-2-(tert-butoxycarbonylamino)-D-threo-L-galacto-decitol
  参考文献：
  名称：

  Synthesis and anti-tumor activity of β-C-glycoside analogs of the immunostimulant KRN7000

  摘要：

  A ring-closing metathesis approach was employed for the synthesis of a beta-C-glycoside analog of the immunostimulant KRN7000. The protected Gglycosyl amino acid derivative 18 was converted to amino-olefin 20, and osmylation served to install the diol unit as a mixture of separable syn and anti isomers. Deprotection to the hydroxy-amine 21 was followed by N-acylation and debenzylation to deliver the target compound 5. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.07.163

文献信息

• Stereoselective synthesis of the C-linked analogue of β-d-galactopyranosyl-l-serine
  作者：Alessandro Dondoni、Alberto Marra、Alessandro Massi

  DOI：10.1016/s0040-4020(98)83019-6

  日期：1998.3

  The coupling of the D-serinal derivative 7 with the D-galactopyranosylmethylene phosphorane generated from the phosphonium salt 6 and reduction of the resulting alkene led to the C-glycosylated amino alcohol 9 that in turn was oxidized to the title amino acid in 44% overall yield. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis of β-<scp>d</scp>-Galactosyl Ceramide Methylene Isostere
  作者：Alessandro Dondoni、Daniela Perrone、Elisa Turturici

  DOI：10.1021/jo990398l

  日期：1999.7.1

  The methylene isostere of the glycosphingolipid beta-D-galactosyl N-palmitoyl C-18 ceramide has been synthesized by a linear reaction sequence starting from a beta-linked D-galactopyranosyl aldehyde. First, this sugar aldehyde was converted into a methylenephosphorane which in turn was coupled with N-Boc serinal acetonide. The double bond of the resulting olefin was reduced and the oxazolidine ring was cleaved and oxidized to give a C-glycosyl N-Boc alpha-amino butanal (three-carbon chain elongation). Then, an additional C-15 carbon chain was installed by addition of lithium 1-pentadecyne to the above glycosyl amino aldehyde. The syn/anti ratio (70:30) of the resulting mixture of amino alcohols was reversed (5:95) by an oxidation-reduction sequence to achieve the same stereochemistry as in the hydrophilic head of D-erythro-sphingosines. The major product was subjected to the reduction of the triple bond with LiAlH4 to give the olefin with E geometry. Finally the N-amide group was installed by reaction with palmitoyl chloride and the O-benzyl protective groups of the sugar moiety were removed by treatment with lithium in liquid NH3-THF. The final product was characterized as the O-acetyl derivative.
• Synthesis of carbon-linked glycopeptides as stable glycopeptide models
  作者：Carolyn R. Bertozzi、Paul D. Hoeprich、Mark D. Bednarski

  DOI：10.1021/jo00049a005

  日期：1992.11

  A C-glycosyl analog of beta-Gal-O-Ser has been synthesized and incorporated by automated solid-phase peptide synthesis into a hydrolytically stable, alpha-helical C-glycopeptide.