2-(trimethylsilyl)ethyl 2-(benzyloxy)-6-(3-((2S,6S)-6-((3S,4R,6S,E)-6-(benzyloxy)-7-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-4-((tert-butyldimethylsilyl)oxy)-3-methylhept-1-en-1-yl)tetrahydro-2H-pyran-2-yl)propyl)benzoate

Base Information

Chemical Name:2-(trimethylsilyl)ethyl 2-(benzyloxy)-6-(3-((2S,6S)-6-((3S,4R,6S,E)-6-(benzyloxy)-7-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-4-((tert-butyldimethylsilyl)oxy)-3-methylhept-1-en-1-yl)tetrahydro-2H-pyran-2-yl)propyl)benzoate
CAS No.:1325653-89-1
Molecular Formula:C₆₄H₉₂O₉Si₂
Molecular Weight:1061.6
Hs Code.:

2-(trimethylsilyl)ethyl 2-(benzyloxy)-6-(3-((2S,6S)-6-((3S,4R,6S,E)-6-(benzyloxy)-7-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-4-((tert-butyldimethylsilyl)oxy)-3-methylhept-1-en-1-yl)tetrahydro-2H-pyran-2-yl)propyl)benzoate

Synonyms:2-(trimethylsilyl)ethyl 2-(benzyloxy)-6-(3-((2S,6S)-6-((3S,4R,6S,E)-6-(benzyloxy)-7-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-4-((tert-butyldimethylsilyl)oxy)-3-methylhept-1-en-1-yl)tetrahydro-2H-pyran-2-yl)propyl)benzoate

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Chemical Property of 2-(trimethylsilyl)ethyl 2-(benzyloxy)-6-(3-((2S,6S)-6-((3S,4R,6S,E)-6-(benzyloxy)-7-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-4-((tert-butyldimethylsilyl)oxy)-3-methylhept-1-en-1-yl)tetrahydro-2H-pyran-2-yl)propyl)benzoate

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Technology Process of 2-(trimethylsilyl)ethyl 2-(benzyloxy)-6-(3-((2S,6S)-6-((3S,4R,6S,E)-6-(benzyloxy)-7-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-4-((tert-butyldimethylsilyl)oxy)-3-methylhept-1-en-1-yl)tetrahydro-2H-pyran-2-yl)propyl)benzoate

There total 31 articles about 2-(trimethylsilyl)ethyl 2-(benzyloxy)-6-(3-((2S,6S)-6-((3S,4R,6S,E)-6-(benzyloxy)-7-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-4-((tert-butyldimethylsilyl)oxy)-3-methylhept-1-en-1-yl)tetrahydro-2H-pyran-2-yl)propyl)benzoate 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: 60.0%

: 1325653-39-1
2-(trimethylsilyl)ethyl 2-(benzyloxy)-6-(3-((2S,6S)-6-vinyltetrahydro-2H-pyran-2-yl)propyl)benzoate

: 1325653-37-9
benzyl 2-((2R,6S)-6-((2S,4R,5S)-2-(benzyloxy)-4-((tert-butyldimethylsilyl)oxy)-5-methylhept-6-en-1-yl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate

: 1325653-89-1
2-(trimethylsilyl)ethyl 2-(benzyloxy)-6-(3-((2S,6S)-6-((3S,4R,6S,E)-6-(benzyloxy)-7-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-4-((tert-butyldimethylsilyl)oxy)-3-methylhept-1-en-1-yl)tetrahydro-2H-pyran-2-yl)propyl)benzoate

Guidance literature:: With Hoveyda-Grubbs catalyst second generation; In chlorobenzene; at 85 ℃; for 10h; optical yield given as %de; Inert atmosphere;
DOI:10.1021/ol201863b

Reference yield:

: 864498-77-1
benzyl 2-((2R,6S)-6-((S)-2-(benzyloxy)-4-oxobutyl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate

: 1325653-89-1
2-(trimethylsilyl)ethyl 2-(benzyloxy)-6-(3-((2S,6S)-6-((3S,4R,6S,E)-6-(benzyloxy)-7-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-4-((tert-butyldimethylsilyl)oxy)-3-methylhept-1-en-1-yl)tetrahydro-2H-pyran-2-yl)propyl)benzoate

Guidance literature:: Multi-step reaction with 3 steps

1: boron trifluoride diethyl etherate / tetrahydrofuran; diethyl ether; hexane / 4 h / -78 °C / Inert atmosphere

2: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

3: Hoveyda-Grubbs catalyst second generation / chlorobenzene / 10 h / 85 °C / Inert atmosphere

With 2,6-dimethylpyridine; Hoveyda-Grubbs catalyst second generation; boron trifluoride diethyl etherate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; chlorobenzene;
DOI:10.1021/ol201863b

Reference yield:

: benzyl 2-((2R,6S)-6-((R)-2-hydroxypent-4-en-1-yl)tetrahydro-2H-pyran-2-yl)-2-methylpropanoate

: 1325653-89-1
2-(trimethylsilyl)ethyl 2-(benzyloxy)-6-(3-((2S,6S)-6-((3S,4R,6S,E)-6-(benzyloxy)-7-((2S,6R)-6-(1-(benzyloxy)-2-methyl-1-oxopropan-2-yl)tetrahydro-2H-pyran-2-yl)-4-((tert-butyldimethylsilyl)oxy)-3-methylhept-1-en-1-yl)tetrahydro-2H-pyran-2-yl)propyl)benzoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C / Inert atmosphere

1.2: 2 h / 0 °C / Inert atmosphere

2.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 19 h / Inert atmosphere

3.1: sodium periodate / tetrahydrofuran; water / 2 h / Inert atmosphere

4.1: boron trifluoride diethyl etherate / tetrahydrofuran; diethyl ether; hexane / 4 h / -78 °C / Inert atmosphere

5.1: 2,6-dimethylpyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

6.1: Hoveyda-Grubbs catalyst second generation / chlorobenzene / 10 h / 85 °C / Inert atmosphere

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; Hoveyda-Grubbs catalyst second generation; boron trifluoride diethyl etherate; sodium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; chlorobenzene; acetone;
DOI:10.1021/ol201863b