(4S,5R,6R)-4-Acetoxy-5-acetylamino-2-dodecylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester | 957218-46-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4S,5R,6R)-4-Acetoxy-5-acetylamino-2-dodecylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• 英文别名: methyl (4S,5R,6R)-5-acetamido-4-acetyloxy-2-dodecylsulfanyl-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 957218-46-1
• 化学式: C₃₂H₅₃NO₁₂S
• 分子量: 675.838
• InChiKey: XGRWMLJNFIYXET-FLQIKSFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  46
• 可旋转键数：
  26
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  195
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside 、 (4S,5R,6R)-4-Acetoxy-5-acetylamino-2-dodecylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 3 A molecular sieve 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以50%的产率得到2-(trimethylsilyl)ethyl (N-acetyl-4,7,8,9-tetra-O-acetyl-1-methyl-α-neuraminosyl)-(2,3)-2,6-bis-O-(phenylmethyl)-β-D-galactopyranosyl-(1,4)-2,3,6-tris-O-(phenylmethyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of a useful lauryl thioglycoside of sialic acid and its application

  摘要：

  An efficient synthesis of a useful thioglycosyl donor 2 was accomplished directly from known peracetylated sialic acid methvl ester and 1-dodecanethiol (lauryl mercaptan) in the presence of BF3-OEt2. The reactivities of the lauryl glycosides for glycosidation by means of TMSOTf as a convenient promoter were investigated, and the lauryl thioglycoside showed satisfactory activities. Further transformation of the lauryl glycoside was also attempted to give a 5-azide analogue 14 of the sialic acid, which was also reacted with a secondary alcohol in the presence of TMSOTf to give known glycoside 15 in high yield. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.105
• 作为产物：
  描述：

  methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 、 十二硫醇 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以84%的产率得到(4S,5R,6R)-4-Acetoxy-5-acetylamino-2-dodecylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of N,N-Ac,Boc laurylthio sialoside and its application to O-sialylation

  摘要：

  The combination of the 5-N-tert-butoxycarbonyl (Boc) group of laurylthio sialoside and cyclopentyl methyl ether (CPME) as a solvent enhanced the reactivity and alpha-selectivity of the sialyl donor during sialylation. Selective deprotection of the N-Boc group of sialoside, including an acid-sensitive isopropylidene function, was successfully achieved by Yb(OTf)(3)-SiO2. Transformation of NN-Ac,Boc into an N-acetylglycolyl group of sialoglycoside was easily performed via selective N-deacylation of the mixed Ac-N-Boc carbamate, subsequent Boc group removal, and acylation. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.08.088