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

Base Information

• Chemical Name: 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
• CAS No.: 864498-72-6
• Molecular Formula: C₅₅H₈₀O₉Si
• Molecular Weight: 913.32
• Mol file: 864498-72-6.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 42 articles about 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 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: 99.0%

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) + t-butyldimethylsiyl triflate (69739-34-0) → 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 (864498-72-6)

Guidance literature:

With triethylamine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1021/ol0515006

Reference yield: 92.0%

benzyl 2-((2R,6S)-6-((2S,4R,5S,6E)-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-methylhept-6-en-1-yl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate (1325653-88-0) → 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 (864498-72-6)

Guidance literature:

With sodium acetate; toluene-4-sulfonic acid hydrazide; In 1,2-dimethoxyethane; water; at 100 ℃; for 4h; Inert atmosphere;

DOI:10.1021/ol201863b

Reference yield:

benzyl 2-((2R,6S)-6-((2R,4R,5S)-2-(benzyloxy)-4-hydroxy-5-methylhept-6-en-1-yl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate (864498-78-2) → 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 (864498-72-6)

Guidance literature:

Multi-step reaction with 7 steps

1: CH₂Cl₂ / 1 h

2: Rh(acac)(CO)2 / benzene / 20 h / 60 °C / high pressure

3: 1.27 g / n-Bu₄NF / tetrahydrofuran / 2 h / Heating

4: 85 percent / second generation Grubbs catalyst / CH₂Cl₂ / 8 h / Heating

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

6: 0.058 g / triethylsilane; boron trifluoride-diethyl etherate / CH₂Cl₂ / -78 - 0 °C

7: 99 percent / triethylamine / CH₂Cl₂ / -78 - 20 °C

With triethylsilane; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; triethylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; acetylacetonatodicarbonylrhodium(l); Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; benzene;

DOI:10.1021/ol0515006

upstream raw materials:

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

t-butyldimethylsiyl triflate

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

Downstream raw materials:

(2S,4R,5S)-2-(benzyloxy)-7-((2S,6S)-6-(3-(3-(benzyloxy)-2-((2-(trimethylsilyl)ethoxy)carbonyl)phenyl)propyl)tetrahydro-2H-pyran-2-yl)-1-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-5-methylheptan-4-yl 2-(3-((2S,6S)-6-((3S,4R,6S)-6-(benzyloxy)-7-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-4-((tert-butyldimethylsilyl)oxy)-3-methylheptyl)tetrahydro-2H-pyran-2-yl)propyl)-6-hydroxybenzoate