(1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-N-(hex-5-yn-1-yl)-5-methylcyclohexanecarboxamide

Base Information

Chemical Name:(1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-N-(hex-5-yn-1-yl)-5-methylcyclohexanecarboxamide
CAS No.:1365478-34-7
Molecular Formula:C₄₂H₆₁NO₁₅
Molecular Weight:819.944
Hs Code.:

(1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-N-(hex-5-yn-1-yl)-5-methylcyclohexanecarboxamide

Synonyms:(1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-N-(hex-5-yn-1-yl)-5-methylcyclohexanecarboxamide

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Chemical Property of (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-N-(hex-5-yn-1-yl)-5-methylcyclohexanecarboxamide

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Technology Process of (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-N-(hex-5-yn-1-yl)-5-methylcyclohexanecarboxamide

There total 9 articles about (1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-N-(hex-5-yn-1-yl)-5-methylcyclohexanecarboxamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

: 1365478-29-0
(1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-5-methyl-N-[6-(trimethylsilyl)hex-5-yn-1-yl]cyclohexanecarboxamide

: 1365478-34-7
(1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-N-(hex-5-yn-1-yl)-5-methylcyclohexanecarboxamide

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; Inert atmosphere;
DOI:10.1021/ja4029582

Reference yield: 87.0%

: 1365478-34-7
(1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-N-(hex-5-yn-1-yl)-5-methylcyclohexanecarboxamide

Guidance literature:

Reference yield:

: 103437-52-1
6-trimethylsilanyl-hex-5-yn-1-ol

: 1365478-34-7
(1R,3R,4R,5S)-3-[2-O-benzoyl-3-O-((1S)-1-carboxy-2-cyclohexylethyl)-(β-D-galactopyranosyl)oxy]-4-[(α-L-fucopyranosyl)oxy]-N-(hex-5-yn-1-yl)-5-methylcyclohexanecarboxamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: triethylamine / dichloromethane / 1.5 h / -15 °C

2.1: sodium azide / N,N-dimethyl-formamide / 1 h / Inert atmosphere

3.1: water; triphenylphosphine / tetrahydrofuran / 4.5 h / 50 - 60 °C

4.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; benzotriazol-1-ol / N,N-dimethyl-formamide / 0.08 h / 20 °C

4.2: 2 h / 20 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

With sodium azide; tetrabutyl ammonium fluoride; water; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja4029582