2-[(2R,6S)-6-((2R,4R,5S)-2-Benzyloxy-7-{(2S,6S)-6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-hydroxy-5-methyl-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester

Base Information

• Chemical Name: 2-[(2R,6S)-6-((2R,4R,5S)-2-Benzyloxy-7-{(2S,6S)-6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-hydroxy-5-methyl-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester
• CAS No.: 864498-85-1
• Molecular Formula: C₄₉H₆₆O₉
• Molecular Weight: 799.058
• Mol file: 864498-85-1.mol

Synonyms:2-[(2R,6S)-6-((2R,4R,5S)-2-Benzyloxy-7-{(2S,6S)-6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-hydroxy-5-methyl-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester

Chemical Property of 2-[(2R,6S)-6-((2R,4R,5S)-2-Benzyloxy-7-{(2S,6S)-6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-hydroxy-5-methyl-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(2R,6S)-6-((2R,4R,5S)-2-Benzyloxy-7-{(2S,6S)-6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-hydroxy-5-methyl-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester

There total 15 articles about 2-[(2R,6S)-6-((2R,4R,5S)-2-Benzyloxy-7-{(2S,6S)-6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-hydroxy-5-methyl-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester 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:

2-[(2R,6S)-6-((2R,4R,5S)-2-Benzyloxy-7-{(S)-6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-6-hydroxy-tetrahydro-pyran-2-yl}-4-hydroxy-5-methyl-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester → 2-[(2R,6S)-6-((2R,4R,5S)-2-Benzyloxy-7-{(2S,6S)-6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-hydroxy-5-methyl-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester (864498-85-1)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In dichloromethane; at -78 - 0 ℃;

DOI:10.1021/ol0515006

Reference yield:

4-(2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)butanal (886747-44-0) → 2-[(2R,6S)-6-((2R,4R,5S)-2-Benzyloxy-7-{(2S,6S)-6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-hydroxy-5-methyl-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester (864498-85-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 81 percent / tetrahydrofuran / 0.17 h / 0 °C

2: 93 percent / diisopropylamine; DMSO; sulfur trioxide-pyridine complex / CH₂Cl₂ / 1 h

3: 85 percent / second generation Grubbs catalyst / CH₂Cl₂ / 8 h / Heating

4: H₂ / Lindlar catalyst / methanol; ethyl acetate / 0.67 h / 760 Torr

5: 0.058 g / triethylsilane; boron trifluoride-diethyl etherate / CH₂Cl₂ / -78 - 0 °C

With triethylsilane; boron trifluoride diethyl etherate; hydrogen; sulfur trioxide pyridine complex; dimethyl sulfoxide; diisopropylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

DOI:10.1021/ol0515006

Reference yield:

5-(4-hydroxy-hex-5-enyl)-2,2-dimethyl-benzo[1,3]dioxin-4-one (864498-89-5) → 2-[(2R,6S)-6-((2R,4R,5S)-2-Benzyloxy-7-{(2S,6S)-6-[3-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-hydroxy-5-methyl-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester (864498-85-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / diisopropylamine; DMSO; sulfur trioxide-pyridine complex / CH₂Cl₂ / 1 h

2: 85 percent / second generation Grubbs catalyst / CH₂Cl₂ / 8 h / Heating

3: H₂ / Lindlar catalyst / methanol; ethyl acetate / 0.67 h / 760 Torr

4: 0.058 g / triethylsilane; boron trifluoride-diethyl etherate / CH₂Cl₂ / -78 - 0 °C

With triethylsilane; boron trifluoride diethyl etherate; hydrogen; sulfur trioxide pyridine complex; dimethyl sulfoxide; diisopropylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; Lindlar's catalyst; In methanol; dichloromethane; ethyl acetate;

DOI:10.1021/ol0515006

upstream raw materials:

4-(2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)butanal

2,2-dimethyl-5-(4-oxo-hex-5-enyl)-benzo[1,3]dioxin-4-one

5-(4-hydroxy-hex-5-enyl)-2,2-dimethyl-benzo[1,3]dioxin-4-one

benzyl 2-((2R,6S)-6-((S)-2-(benzyloxy)-4-oxobutyl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate

Downstream raw materials:

benzyl 2-((2R,6S)-6-((2S,4R,5S)-2-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)-7-((2S,6S)-6-(3-(2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)propyl)tetrahydro-2H-pyran-2-yl)-5-methylheptyl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate