(5R,5aR,8aS,9S)-9-((2,2-difluoro-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)ethyl)amino)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one

Base Information

• Chemical Name: (5R,5aR,8aS,9S)-9-((2,2-difluoro-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)ethyl)amino)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one
• CAS No.: 1616619-26-1
• Molecular Formula: C₂₉H₃₃F₂NO₁₂
• Molecular Weight: 625.577

Synonyms:(5R,5aR,8aS,9S)-9-((2,2-difluoro-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)ethyl)amino)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one

Chemical Property of (5R,5aR,8aS,9S)-9-((2,2-difluoro-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)ethyl)amino)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one

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Technology Process of (5R,5aR,8aS,9S)-9-((2,2-difluoro-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)ethyl)amino)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one

There total 14 articles about (5R,5aR,8aS,9S)-9-((2,2-difluoro-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)ethyl)amino)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one 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: 57.0%

(5R,5aR,8aS,9S)-9-((2,2-difluoro-2-((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)ethyl)amino)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one (1616619-34-1) → (5R,5aR,8aS,9S)-9-((2,2-difluoro-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)ethyl)amino)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one (1616619-26-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; for 6h; Sonication;

Reference yield:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) → (5R,5aR,8aS,9S)-9-((2,2-difluoro-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)ethyl)amino)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one (1616619-26-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: zinc-copper couple / tetrahydrofuran / 3 h / Reflux; Inert atmosphere

2.1: pyridine; thionyl chloride / dichloromethane / 0.17 h / 0 - 5 °C / Inert atmosphere

3.1: tri-n-butyl-tin hydride; 1,1'-azobis (cyclohexanecarbonitrile) / toluene / 1 h / Reflux; Inert atmosphere

4.1: diisobutylaluminium hydride / toluene / 1 h / -78 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / toluene; water / 18 h / Dean-Stark; Inert atmosphere; Reflux

5.2: 3 h / 0 - 20 °C / Inert atmosphere; Dean-Stark

6.1: hydrogen; palladium 10% on activated carbon / methanol / 3.5 h / Sonication

With pyridine; thionyl chloride; 1,1'-azobis (cyclohexanecarbonitrile); palladium 10% on activated carbon; zinc-copper couple; hydrogen; tri-n-butyl-tin hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; dichloromethane; water; toluene;

Reference yield:

methyl D-glucopyranoside (97-30-3,617-04-9,709-50-2,1824-94-8,2152-78-5,3396-99-4,6819-48-3,18469-06-2,20550-04-3,22277-65-2,29411-57-2,35437-40-2,35437-43-5,36191-11-4,36191-12-5,39598-79-3,39598-80-6,39598-89-5,51023-63-3,51223-62-2,51224-38-5,51224-39-6,51224-40-9,51224-41-0,51819-81-9,51819-82-0,51819-83-1,56688-81-4,62279-53-2,64281-79-4,64281-80-7,64912-19-2,66101-73-3,78184-90-4,84368-39-8,84368-40-1,84368-41-2,92142-37-5,93302-26-2,103421-28-9,115794-08-6,3149-68-6) → (5R,5aR,8aS,9S)-9-((2,2-difluoro-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)ethyl)amino)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one (1616619-26-1)

Guidance literature:

Multi-step reaction with 11 steps

1.1: tetra-(n-butyl)ammonium iodide; sodium hydride / N,N-dimethyl-formamide; mineral oil / 3.5 h / 0 - 20 °C / Inert atmosphere

1.2: 20 h / 20 °C / Inert atmosphere

2.1: acetic acid; water; sulfuric acid / 1 h / 110 °C

3.1: acetic anhydride; dimethyl sulfoxide / 18 h / 20 °C / Inert atmosphere

4.1: zinc-copper couple / tetrahydrofuran / 3 h / Reflux; Inert atmosphere

5.1: pyridine; thionyl chloride / dichloromethane / 0.17 h / 0 - 5 °C / Inert atmosphere

6.1: tri-n-butyl-tin hydride; 1,1'-azobis (cyclohexanecarbonitrile) / toluene / 1 h / Reflux; Inert atmosphere

7.1: lithium hydroxide; water / ethanol / 18 h / 20 °C / Inert atmosphere

8.1: dimethylsulfide borane complex / tetrahydrofuran / 0 °C / Reflux

9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; dimethyl sulfoxide / 24.5 h / 20 °C

10.1: sodium cyanoborohydride; trifluoroacetic acid / dichloromethane / 0 °C / Inert atmosphere

10.2: 40 h / 0 - 20 °C / Inert atmosphere

11.1: hydrogen; palladium 10% on activated carbon / methanol / 6 h / Sonication

With pyridine; thionyl chloride; 1,1'-azobis (cyclohexanecarbonitrile); dimethylsulfide borane complex; sulfuric acid; palladium 10% on activated carbon; zinc-copper couple; water; hydrogen; tri-n-butyl-tin hydride; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium cyanoborohydride; acetic acid; dimethyl sulfoxide; trifluoroacetic acid; lithium hydroxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; mineral oil;

upstream raw materials:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

2,2-difluoro-2-((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)ethanol

2,2-difluoro-2-((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)ethane-1,1-diol

(5R,5aR,8aS,9S)-9-((2,2-difluoro-2-((2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)ethyl)amino)-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one

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