CAS: 84635-54-1; Methyl 2,3,4-Tri-O-Acetyl-1-Thio-β-L-Fucopyranoside

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52645-73-5 41670-79-5 64550-71-6

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Trimethyl(methylthio)silane 1,2,3,4-tetra-O-acetyl-L-fucopyranose acetic anhydride methyl 1-thio-β-L-fucopyranoside(2R,3S,4R,5S,6S)-2-Methyl-6-methylsulfanyl-tetrahydro-pyran-3,4,5-triol 2,3,4-tri-O-acetyl-α-L-fucopyranosyl bromide (2S,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-methyl-6-methylsulfanyl-tetrahydro-pyran 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1-> 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoseO-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-(1- 3)-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1- 4)]-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranose

📜6-Deoxy-L-Galactose置于碘,六甲基二硅氮烷体系中,用 二氯甲烷 作为反应溶剂,化学反应 1.75H,反应生成 2,3,4-三-O-乙酰基-1-硫代-β-L-岩藻糖苷甲酯
参考文献:Streamlined Synthesis Of Per-O-Acetylated Sugars,Glycosyl Iodides,Or Thioglycosides From Unprotected Reducing Sugars1
标题:Streamlined Synthesis Of Per-O-Acetylated Sugars,Glycosyl Iodides,Or Thioglycosides From Unprotected Reducing Sugars1
摘要:Solvent-Free Per-O-Acetylation Of Sugars With Stoichiometric Acetic Anhydride And Catalytic Iodine Proceeds In High Yield (90-99%) To Give Exclusively Pyranose Products As Anomeric Mixtures. Without Workup,Subsequent Anomeric Substitution Employing Iodine In The Presence Of Hexamethyldisilane (I.E.,Tms-I Generated In Situ) Gives The Corresponding Glycosyl Iodides In 75-95% Isolated Yield. Alternatively,And Without Workup,Further Treatment With Dimethyl Disulfide Or Thiol (Ethanethiol Or Thiocresol) Gives Anomerically Pure Thioglycosides In More Than 75% Overall Yield.
DOI:10.1021/jo048890E