(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-{5-[(4-{(1E)-4-[(1-{[2-(dimethylamino)ethyl]amino}-2-methyl-1-oxopropan-2-yl)amino]-3,3-dimethyl-4-oxobut-1-en-1-yl}phenyl)methyl]-2-methoxy-4-(propan-2-yl)phenyl}-D-glucitol

Base Information

• Chemical Name: (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-{5-[(4-{(1E)-4-[(1-{[2-(dimethylamino)ethyl]amino}-2-methyl-1-oxopropan-2-yl)amino]-3,3-dimethyl-4-oxobut-1-en-1-yl}phenyl)methyl]-2-methoxy-4-(propan-2-yl)phenyl}-D-glucitol
• CAS No.: 1240305-16-1
• Molecular Formula: C₄₅H₆₃N₃O₁₂
• Molecular Weight: 838.008

Synonyms:(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-{5-[(4-{(1E)-4-[(1-{[2-(dimethylamino)ethyl]amino}-2-methyl-1-oxopropan-2-yl)amino]-3,3-dimethyl-4-oxobut-1-en-1-yl}phenyl)methyl]-2-methoxy-4-(propan-2-yl)phenyl}-D-glucitol

Chemical Property of (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-{5-[(4-{(1E)-4-[(1-{[2-(dimethylamino)ethyl]amino}-2-methyl-1-oxopropan-2-yl)amino]-3,3-dimethyl-4-oxobut-1-en-1-yl}phenyl)methyl]-2-methoxy-4-(propan-2-yl)phenyl}-D-glucitol

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Technology Process of (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-{5-[(4-{(1E)-4-[(1-{[2-(dimethylamino)ethyl]amino}-2-methyl-1-oxopropan-2-yl)amino]-3,3-dimethyl-4-oxobut-1-en-1-yl}phenyl)methyl]-2-methoxy-4-(propan-2-yl)phenyl}-D-glucitol

There total 19 articles about (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-{5-[(4-{(1E)-4-[(1-{[2-(dimethylamino)ethyl]amino}-2-methyl-1-oxopropan-2-yl)amino]-3,3-dimethyl-4-oxobut-1-en-1-yl}phenyl)methyl]-2-methoxy-4-(propan-2-yl)phenyl}-D-glucitol 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: 94.0%

2-{[(3E)-4-(4-{[4-methoxy-2-(propan-2-yl)-5-{(2S,3S,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl}phenyl]methyl}phenyl)-2,2-dimethylbut-3-enoyl]amino}-2-methylpropanoic acid + N,N-dimethylethylenediamine (108-00-9) → (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-{5-[(4-{(1E)-4-[(1-{[2-(dimethylamino)ethyl]amino}-2-methyl-1-oxopropan-2-yl)amino]-3,3-dimethyl-4-oxobut-1-en-1-yl}phenyl)methyl]-2-methoxy-4-(propan-2-yl)phenyl}-D-glucitol (1240305-16-1)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In chloroform; N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.bmc.2018.12.015

Reference yield:

3-isopropylhydroxybenzene (618-45-1) → (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-{5-[(4-{(1E)-4-[(1-{[2-(dimethylamino)ethyl]amino}-2-methyl-1-oxopropan-2-yl)amino]-3,3-dimethyl-4-oxobut-1-en-1-yl}phenyl)methyl]-2-methoxy-4-(propan-2-yl)phenyl}-D-glucitol (1240305-16-1)

Guidance literature:

Multi-step reaction with 15 steps

1.1: potassium iodate; iodine; acetic acid / water / 20 h / 20 °C

2.1: potassium carbonate / acetonitrile / 3.5 h

3.1: n-butyllithium / hexane; tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere

3.2: 0.58 h / -78 °C / Inert atmosphere

4.1: methanesulfonic acid / 2 h / 20 °C / Inert atmosphere

5.1: pyridine / 14 h / 20 °C / Inert atmosphere

6.1: boron trifluoride diethyl etherate; triethylsilane / chloroform; acetonitrile / 1 h / 4 °C / Inert atmosphere

7.1: acetic acid; bromine / 1 h / 20 °C

8.1: sodium methylate / methanol / 2 h / 20 °C

9.1: triethylamine / N,N-dimethyl-formamide / 2 h / 4 - 20 °C

10.1: n-butyllithium / hexane; tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

10.2: 0.75 h / -78 °C / Inert atmosphere

11.1: methanesulfonic acid / methanol / 14 h / 20 °C / Inert atmosphere

12.1: pyridine / 5 h / 20 °C / Inert atmosphere

13.1: boron trifluoride diethyl etherate; triethylsilane / chloroform; acetonitrile / 0.67 h / 4 °C / Inert atmosphere

14.1: palladium diacetate; tris-(o-tolyl)phosphine; triethylamine / acetonitrile / 0.5 h / 120 °C / Inert atmosphere; Microwave irradiation

15.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; chloroform / 20 °C

With pyridine; triethylsilane; potassium iodate; n-butyllithium; methanesulfonic acid; boron trifluoride diethyl etherate; bromine; iodine; sodium methylate; palladium diacetate; potassium carbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; tris-(o-tolyl)phosphine; In tetrahydrofuran; methanol; hexane; chloroform; water; N,N-dimethyl-formamide; acetonitrile; 14.1: |Heck Reaction;

DOI:10.1016/j.bmc.2018.12.015

Reference yield:

1-iodo-2-methoxy-4-(propan-2-yl)benzene (1240304-64-6) → (1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-{5-[(4-{(1E)-4-[(1-{[2-(dimethylamino)ethyl]amino}-2-methyl-1-oxopropan-2-yl)amino]-3,3-dimethyl-4-oxobut-1-en-1-yl}phenyl)methyl]-2-methoxy-4-(propan-2-yl)phenyl}-D-glucitol (1240305-16-1)

Guidance literature:

Multi-step reaction with 13 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 0.08 h / -78 °C / Inert atmosphere

1.2: 0.58 h / -78 °C / Inert atmosphere

2.1: methanesulfonic acid / 2 h / 20 °C / Inert atmosphere

3.1: pyridine / 14 h / 20 °C / Inert atmosphere

4.1: boron trifluoride diethyl etherate; triethylsilane / chloroform; acetonitrile / 1 h / 4 °C / Inert atmosphere

5.1: acetic acid; bromine / 1 h / 20 °C

6.1: sodium methylate / methanol / 2 h / 20 °C

7.1: triethylamine / N,N-dimethyl-formamide / 2 h / 4 - 20 °C

8.1: n-butyllithium / hexane; tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

8.2: 0.75 h / -78 °C / Inert atmosphere

9.1: methanesulfonic acid / methanol / 14 h / 20 °C / Inert atmosphere

10.1: pyridine / 5 h / 20 °C / Inert atmosphere

11.1: boron trifluoride diethyl etherate; triethylsilane / chloroform; acetonitrile / 0.67 h / 4 °C / Inert atmosphere

12.1: palladium diacetate; tris-(o-tolyl)phosphine; triethylamine / acetonitrile / 0.5 h / 120 °C / Inert atmosphere; Microwave irradiation

13.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide; chloroform / 20 °C

With pyridine; triethylsilane; n-butyllithium; methanesulfonic acid; boron trifluoride diethyl etherate; bromine; sodium methylate; palladium diacetate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; tris-(o-tolyl)phosphine; In tetrahydrofuran; methanol; hexane; chloroform; N,N-dimethyl-formamide; acetonitrile; 12.1: |Heck Reaction;

DOI:10.1016/j.bmc.2018.12.015

upstream raw materials:

3-isopropylhydroxybenzene

1-iodo-2-methoxy-4-(propan-2-yl)benzene

(1S)-1,5-anhydro-1-[5-bromo-2-methoxy-4-(propan-2-yl)phenyl]-2,3,4,6-tetrakis-O-(trimethylsilyl)-D-glucitol

(1S)-2,3,4,6-tetra-O-acetyl-1,5-anhydro-1-{5-[(4-bromophenyl)methyl]-2-methoxy-4-(propan-2-yl)phenyl}-D-glucitol

Downstream raw materials:

(E)-N-(1-((2-(dimethylamino)ethyl)amino)-2-methyl-1-oxopropan-2-yl)-4-(4-(2-isopropyl-4-methoxy-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)phenyl)-2,2-dimethylbut-3-enamide

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