S-ethyl 3,4-O-isopropylidene-2-O-methyl-1-thio-β-D-fucopyranoside | 207917-23-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: S-ethyl 3,4-O-isopropylidene-2-O-methyl-1-thio-β-D-fucopyranoside
• 英文别名: (3aR,4S,6R,7S,7aR)-6-ethylsulfanyl-7-methoxy-2,2,4-trimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran
• CAS: 207917-23-5
• 化学式: C₁₂H₂₂O₄S
• 分子量: 262.37
• InChiKey: TXAJKIGXHRESOM-UNQZSWDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  62.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  S-ethyl 3,4-O-isopropylidene-2-O-methyl-1-thio-β-D-fucopyranoside 在 三氟甲磺酸 N-碘代丁二酰亚胺 、 iodonium(di-γ-collidine) perchlorate 、 4 A molecular sieve 、 二正丁基氧化锡 、 碳酸氢钠 、 溶剂黄146 、 cesium fluoride 作用下， 以 乙醚 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 39.42h， 生成 3-benzyloxycarbonylaminopropyl 6-deoxy-2-O-<2,4-di-O-benzoyl-3-O-(3-O-benzyl-4-O-chloroacetyl-2-O-methyl-α-L-fucopyranosyl)-α-L-rhamnopyranosyl>-3,4-O-isopropylidene-α-L-talopyranoside
  参考文献：
  名称：

  Iodonium ion-assisted synthesis of a haptenic tetrasaccharide fragment corresponding to the inner cell-wall glycopeptidolipid of Mycobacterium avium serotype 4

  摘要：

  Condensation of ethyl 2,4-di-O-benzoyl-1-thio-alpha-L-rhamnopyranoside with ethyl 3-O-benzyl-4-O-chloroacetyl-2-O-methyl-1-thio-beta-L-fucopyranoside in the presence of iodonium di-sym-collidine perchlorate afforded exclusively ethyl 2,4-di-O-benzoyl-3-O-(3-O-benzyl-4-O-chloroacetyl-2-O-methyl-alpha-L-fucopyranosyl)-1-thio-alpha-L-rhamnopyranoside. This disaccharide derivative was extended at C-1 with 3-benzyloxycarbonylaminopropyl 6-deoxy-3,4-O-isopropylidene-alpha-L-talopyranoside, using N-iodosuccinimide and triflic acid as the catalyst, to furnish 3-benzyloxycarbonylaminopropyl 6-deoxy-2-O[2,4-di-O-benzoyl-3-O-(3-O-benzyl-4-O-chloroacetyl-2-O-methyl-alpha-L-fucopyranosyl)-alpha-L-rhamnopyranosyl]-3,4-0-isopropylidene-alpha-L-talopyranoside (20). Selective removal of the chloroacetyl group from 20, followed by condensation with ethyl 2,3-di-O-benzoyl-4-O-methyl-1-thio-alpha-L-rhamnopyranoside in the presence of the same thiophilic promoter, yielded a fully protected tetrasaccharide derivative. Deprotection of the latter gave the target compound 3-aminopropyl 6-deoxy-2-O-{3-O-[2-O-methyl-(4-O-methyl-alpha-L-rhamnopyranosyl)-alpha-L-fucopyranosyl]-alpha-L-rhamnopyranosyl}alpha-L-talopyranoside (1).

  DOI：

  10.1016/0008-6215(93)80102-k
• 作为产物：
  描述：

  ethyl 1-thio-β-L-fucopyranoside 在 氢氧化钾 、 对甲苯磺酸 作用下， 以 二甲基亚砜 为溶剂， 反应 24.5h， 生成 S-ethyl 3,4-O-isopropylidene-2-O-methyl-1-thio-β-D-fucopyranoside
  参考文献：
  名称：

  Synthesis of lipooligosaccharides related to nodulation factors ofRhizobium sp. NGR234

  摘要：

  Trisaccharide analogs of natural nodulation factors from Rhizobium sp. NGR234, namely, 2-acetamido-2-deoxy-4-O-(2-deoxy-2-hexadecanamido-beta-D-glucopyranosyl)-6-O- (2-O-methyl-alpha-L-fucopyranosyl)-D-glucopyranose and its derivatives containing a 4-O-acetyl or a 3-O-sulfo group at the L-fucose residue, were synthesized. The oligosaccharides synthesized were shown to possess biological activity.

  DOI：

  10.1007/bf02495661

文献信息

• SYNTHESIS OF O-METHYLATED DISACCHARIDES RELATED TO EXCRETORY/ SECRETORY ANTIGENS OF TOXOCARA LARVAE1
  作者：Hassan Amer、Andreas Hofinger、Michael Puchberger、Paul Kosma

  DOI：10.1081/car-100108285

  日期：——

  The disaccharides 2-O-Me-alpha -L-Fucp-(1 -->2)-beta -D-Galp-(1 --> OAllyl) 12, alpha -L-Fucp-(1 -->2)-4-O-Me-beta -D-Galp-(1 --> OAllyl) 15, and 2-O-Me-alpha -L-Fucp-(1 -->2)-4-O-Me-beta -D-Galp-(1 --> OAllyl) 18 have been synthesized. Glycosylation reactions were performed using ethyl 1-thiofueopyranosides as glycosyl donors and N-iodosuceiniinide-triflic acid as the activating agent. The O-methylated disaccharides correspond to highly immunogenic O-glycan antigens occurring at the surface of Toxocara canis and Toxocara cati larvae.
• Iodonium ion-assisted synthesis of a haptenic tetrasaccharide fragment corresponding to the inner cell-wall glycopeptidolipid of Mycobacterium avium serotype 4
  作者：Helene M. Zuurmond、Gerrit H. Veeneman、Gijs A. van der Marel、Jacques H. van Boom

  DOI：10.1016/0008-6215(93)80102-k

  日期：1993.3

  Condensation of ethyl 2,4-di-O-benzoyl-1-thio-alpha-L-rhamnopyranoside with ethyl 3-O-benzyl-4-O-chloroacetyl-2-O-methyl-1-thio-beta-L-fucopyranoside in the presence of iodonium di-sym-collidine perchlorate afforded exclusively ethyl 2,4-di-O-benzoyl-3-O-(3-O-benzyl-4-O-chloroacetyl-2-O-methyl-alpha-L-fucopyranosyl)-1-thio-alpha-L-rhamnopyranoside. This disaccharide derivative was extended at C-1 with 3-benzyloxycarbonylaminopropyl 6-deoxy-3,4-O-isopropylidene-alpha-L-talopyranoside, using N-iodosuccinimide and triflic acid as the catalyst, to furnish 3-benzyloxycarbonylaminopropyl 6-deoxy-2-O[2,4-di-O-benzoyl-3-O-(3-O-benzyl-4-O-chloroacetyl-2-O-methyl-alpha-L-fucopyranosyl)-alpha-L-rhamnopyranosyl]-3,4-0-isopropylidene-alpha-L-talopyranoside (20). Selective removal of the chloroacetyl group from 20, followed by condensation with ethyl 2,3-di-O-benzoyl-4-O-methyl-1-thio-alpha-L-rhamnopyranoside in the presence of the same thiophilic promoter, yielded a fully protected tetrasaccharide derivative. Deprotection of the latter gave the target compound 3-aminopropyl 6-deoxy-2-O-3-O-[2-O-methyl-(4-O-methyl-alpha-L-rhamnopyranosyl)-alpha-L-fucopyranosyl]-alpha-L-rhamnopyranosyl}alpha-L-talopyranoside (1).
• Synthesis of lipooligosaccharides related to nodulation factors ofRhizobium sp. NGR234
  作者：A. I. Zinin、V. I. Torgov、V. N. Shibaev、A. S. Shashkov、W. J. Broughton

  DOI：10.1007/bf02495661

  日期：1998.3

  Trisaccharide analogs of natural nodulation factors from Rhizobium sp. NGR234, namely, 2-acetamido-2-deoxy-4-O-(2-deoxy-2-hexadecanamido-beta-D-glucopyranosyl)-6-O- (2-O-methyl-alpha-L-fucopyranosyl)-D-glucopyranose and its derivatives containing a 4-O-acetyl or a 3-O-sulfo group at the L-fucose residue, were synthesized. The oligosaccharides synthesized were shown to possess biological activity.