(3R,4S,7R,E)-8-((2S,4S,6R)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-iodotetrahydro-2H-pyran-2-yl)-4,7-dimethyl-1-(trimethylsilyl)oct-5-en-1-yn-3-yl acetate

Base Information

Chemical Name:(3R,4S,7R,E)-8-((2S,4S,6R)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-iodotetrahydro-2H-pyran-2-yl)-4,7-dimethyl-1-(trimethylsilyl)oct-5-en-1-yn-3-yl acetate
CAS No.:1344153-77-0
Molecular Formula:C₃₈H₅₅IO₄Si₂
Molecular Weight:758.928
Hs Code.:

(3R,4S,7R,E)-8-((2S,4S,6R)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-iodotetrahydro-2H-pyran-2-yl)-4,7-dimethyl-1-(trimethylsilyl)oct-5-en-1-yn-3-yl acetate

Synonyms:(3R,4S,7R,E)-8-((2S,4S,6R)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-iodotetrahydro-2H-pyran-2-yl)-4,7-dimethyl-1-(trimethylsilyl)oct-5-en-1-yn-3-yl acetate

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Chemical Property of (3R,4S,7R,E)-8-((2S,4S,6R)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-iodotetrahydro-2H-pyran-2-yl)-4,7-dimethyl-1-(trimethylsilyl)oct-5-en-1-yn-3-yl acetate

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Technology Process of (3R,4S,7R,E)-8-((2S,4S,6R)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-iodotetrahydro-2H-pyran-2-yl)-4,7-dimethyl-1-(trimethylsilyl)oct-5-en-1-yn-3-yl acetate

There total 14 articles about (3R,4S,7R,E)-8-((2S,4S,6R)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-iodotetrahydro-2H-pyran-2-yl)-4,7-dimethyl-1-(trimethylsilyl)oct-5-en-1-yn-3-yl acetate 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: 82.0%

: 1344153-76-9
(3R,4S,7R,E)-8-((2S,4R,6R)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-hydroxytetrahydro-2H-pyran-2-yl)-4,7-dimethyl-1-(trimethylsilyl)oct-5-en-1-yn-3-yl acetate

: 1344153-77-0
(3R,4S,7R,E)-8-((2S,4S,6R)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-iodotetrahydro-2H-pyran-2-yl)-4,7-dimethyl-1-(trimethylsilyl)oct-5-en-1-yn-3-yl acetate

Guidance literature:: With 1H-imidazole; N-iodo-succinimide; triphenylphosphine; In tetrahydrofuran; for 0.666667h; Inert atmosphere;
DOI:10.1002/anie.201102790

Reference yield:

: 1344153-56-5
(5R,6R,E)-6-((tert-butyldimethylsilyl)oxy)-5-methyl-8-(trimethylsilyl)oct-2-en-7-yn-4-one

: 1344153-77-0
(3R,4S,7R,E)-8-((2S,4S,6R)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-iodotetrahydro-2H-pyran-2-yl)-4,7-dimethyl-1-(trimethylsilyl)oct-5-en-1-yn-3-yl acetate

Guidance literature:: Multi-step reaction with 10 steps

1.1: dimethylsulfide borane complex / tetrahydrofuran; toluene / 0.5 h / -20 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: 5,5-dimethyl-1,3-cyclohexadiene / 7 h / 140 °C / Inert atmosphere

3.1: lithium amidotrihydridoborate / tetrahydrofuran; hexane / 0.5 h / 0 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.33 h / 23 °C / Inert atmosphere

5.1: hydrogenchloride; water / tetrahydrofuran / 22 h / 23 °C / Inert atmosphere

6.1: calcium sulfate; boron trifluoride diethyl etherate / dichloromethane / -78 - -40 °C / Inert atmosphere

6.2: pH 7 / Inert atmosphere; aq. phosphate buffer

7.1: pyridine; dmap / dichloromethane / 2 h / Inert atmosphere

8.1: water / 5,5-dimethyl-1,3-cyclohexadiene / 130 °C / Inert atmosphere

9.1: sodium tetrahydroborate / methanol / 0.5 h / -10 °C / Inert atmosphere

9.2: Inert atmosphere

10.1: 1H-imidazole; N-iodo-succinimide; triphenylphosphine / tetrahydrofuran / 0.67 h / Inert atmosphere

With pyridine; 1H-imidazole; hydrogenchloride; dmap; calcium sulfate; sodium tetrahydroborate; N-iodo-succinimide; lithium amidotrihydridoborate; dimethylsulfide borane complex; boron trifluoride diethyl etherate; water; sodium hydrogencarbonate; Dess-Martin periodane; triphenylphosphine; In tetrahydrofuran; methanol; 5,5-dimethyl-1,3-cyclohexadiene; hexane; dichloromethane; toluene; 2.1: Eschenmoser-Claisen rearrangement / 4.1: Dess-Martin oxidation / 6.1: Prins reaction;
DOI:10.1002/anie.201102790

Reference yield:

: 1344153-70-3
(3R,6S,7R,E)-7-((tert-butyldimethylsilyl)oxy)-3,6-dimethyl-9-(trimethylsilyl)non-4-en-8-ynal

: 1344153-77-0
(3R,4S,7R,E)-8-((2S,4S,6R)-6-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-4-iodotetrahydro-2H-pyran-2-yl)-4,7-dimethyl-1-(trimethylsilyl)oct-5-en-1-yn-3-yl acetate

Guidance literature:: Multi-step reaction with 6 steps

1.1: hydrogenchloride; water / tetrahydrofuran / 22 h / 23 °C / Inert atmosphere

2.1: calcium sulfate; boron trifluoride diethyl etherate / dichloromethane / -78 - -40 °C / Inert atmosphere

2.2: pH 7 / Inert atmosphere; aq. phosphate buffer

3.1: pyridine; dmap / dichloromethane / 2 h / Inert atmosphere

4.1: water / 5,5-dimethyl-1,3-cyclohexadiene / 130 °C / Inert atmosphere

5.1: sodium tetrahydroborate / methanol / 0.5 h / -10 °C / Inert atmosphere

5.2: Inert atmosphere

6.1: 1H-imidazole; N-iodo-succinimide; triphenylphosphine / tetrahydrofuran / 0.67 h / Inert atmosphere

With pyridine; 1H-imidazole; hydrogenchloride; dmap; calcium sulfate; sodium tetrahydroborate; N-iodo-succinimide; boron trifluoride diethyl etherate; water; triphenylphosphine; In tetrahydrofuran; methanol; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; 2.1: Prins reaction;
DOI:10.1002/anie.201102790