(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-({1-[2-(5-nitro-1H-indol-1-yl)ethyl]-1H-1,2,3-triazol-4-yl}methyl)cyclohexanecarboxamide

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]-5-methyl-N-({1-[2-(5-nitro-1H-indol-1-yl)ethyl]-1H-1,2,3-triazol-4-yl}methyl)cyclohexanecarboxamide
• CAS No.: 1365478-66-5
• Molecular Formula: C₄₉H₆₄N₆O₁₇
• Molecular Weight: 1009.08
• Mol file: 1365478-66-5.mol

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]-5-methyl-N-({1-[2-(5-nitro-1H-indol-1-yl)ethyl]-1H-1,2,3-triazol-4-yl}methyl)cyclohexanecarboxamide

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]-5-methyl-N-({1-[2-(5-nitro-1H-indol-1-yl)ethyl]-1H-1,2,3-triazol-4-yl}methyl)cyclohexanecarboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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]-5-methyl-N-({1-[2-(5-nitro-1H-indol-1-yl)ethyl]-1H-1,2,3-triazol-4-yl}methyl)cyclohexanecarboxamide

There total 7 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]-5-methyl-N-({1-[2-(5-nitro-1H-indol-1-yl)ethyl]-1H-1,2,3-triazol-4-yl}methyl)cyclohexanecarboxamide 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: 66.0%

1-(2-azidoethyl)-5-nitro-1H-indole (1365478-38-1) + (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-(prop-2-yn-1-yl)cyclohexanecarboxamide (1365478-30-3) → (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-({1-[2-(5-nitro-1H-indol-1-yl)ethyl]-1H-1,2,3-triazol-4-yl}methyl)cyclohexanecarboxamide (1365478-66-5)

Guidance literature:

copper(ll) sulfate pentahydrate; sodium L-ascorbate; In tetrahydrofuran; water; tert-butyl alcohol; for 2h; Inert atmosphere;

Reference yield:

{(1R,3R,4R,5S)-4-[(α-L-fucopyranosyl)oxy]-1-methoxycarbonyl-5-methylcyclohex-3-yl} 2-O-benzoyl-3-O-[(1S)-1-carboxy-2-cyclohexylethyl]-β-D-galactopyranoside (1026073-56-2) → (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-({1-[2-(5-nitro-1H-indol-1-yl)ethyl]-1H-1,2,3-triazol-4-yl}methyl)cyclohexanecarboxamide (1365478-66-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydroxide; water / methanol / 3 h / 20 °C

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

2.2: 3 h / 20 °C / Inert atmosphere

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

4.1: sodium L-ascorbate; copper(ll) sulfate pentahydrate / water; tert-butyl alcohol; tetrahydrofuran / 2 h / Inert atmosphere

With tetrabutyl ammonium fluoride; water; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; sodium hydroxide; copper(ll) sulfate pentahydrate; sodium L-ascorbate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; tert-butyl alcohol;

Reference yield:

(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-methylcyclohexanecarboxylic acid (1365478-25-6) → (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-({1-[2-(5-nitro-1H-indol-1-yl)ethyl]-1H-1,2,3-triazol-4-yl}methyl)cyclohexanecarboxamide (1365478-66-5)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 3 h / 20 °C / Inert atmosphere

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

3.1: sodium L-ascorbate; copper(ll) sulfate pentahydrate / water; tert-butyl alcohol; tetrahydrofuran / 2 h / Inert atmosphere

With tetrabutyl ammonium fluoride; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; copper(ll) sulfate pentahydrate; sodium L-ascorbate; In tetrahydrofuran; water; N,N-dimethyl-formamide; tert-butyl alcohol;

upstream raw materials:

5-nitroindole

{(1R,3R,4R,5S)-4-[(α-L-fucopyranosyl)oxy]-1-methoxycarbonyl-5-methylcyclohex-3-yl} 2-O-benzoyl-3-O-[(1S)-1-carboxy-2-cyclohexylethyl]-β-D-galactopyranoside

(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-methylcyclohexanecarboxylic acid

(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-[3-(trimethylsilyl)prop-2-yn-1-yl]cyclohexanecarboxamide