(4S,5S)-4-[(1S,4R)-6-[(4-Methoxybenzyl)oxy]-1,4-di(methoxymethoxy)-2-hexynyl]-5-[(1S)-1-(methoxymethoxy)ethyl]-2,2-dimethyl-1,3-dioxolane

Base Information

Chemical Name:(4S,5S)-4-[(1S,4R)-6-[(4-Methoxybenzyl)oxy]-1,4-di(methoxymethoxy)-2-hexynyl]-5-[(1S)-1-(methoxymethoxy)ethyl]-2,2-dimethyl-1,3-dioxolane
CAS No.:1308324-49-3
Molecular Formula:C₂₇H₄₂O₁₀
Molecular Weight:526.624
Hs Code.:

Synonyms:(4S,5S)-4-[(1S,4R)-6-[(4-Methoxybenzyl)oxy]-1,4-di(methoxymethoxy)-2-hexynyl]-5-[(1S)-1-(methoxymethoxy)ethyl]-2,2-dimethyl-1,3-dioxolane

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Chemical Property of (4S,5S)-4-[(1S,4R)-6-[(4-Methoxybenzyl)oxy]-1,4-di(methoxymethoxy)-2-hexynyl]-5-[(1S)-1-(methoxymethoxy)ethyl]-2,2-dimethyl-1,3-dioxolane

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Technology Process of (4S,5S)-4-[(1S,4R)-6-[(4-Methoxybenzyl)oxy]-1,4-di(methoxymethoxy)-2-hexynyl]-5-[(1S)-1-(methoxymethoxy)ethyl]-2,2-dimethyl-1,3-dioxolane

There total 11 articles about (4S,5S)-4-[(1S,4R)-6-[(4-Methoxybenzyl)oxy]-1,4-di(methoxymethoxy)-2-hexynyl]-5-[(1S)-1-(methoxymethoxy)ethyl]-2,2-dimethyl-1,3-dioxolane 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: 90.0%

: 1308324-63-1
(1S,4R)-6-[(4-methoxybenzyl)oxy]-4-(methoxymethoxy)-1-{(4S,5S)-5-[(1S)-1-(methoxymethoxy)ethyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-hexyn-1-ol

: 107-30-2
chloromethyl methyl ether

: 1308324-49-3
(4S,5S)-4-[(1S,4R)-6-[(4-Methoxybenzyl)oxy]-1,4-di(methoxymethoxy)-2-hexynyl]-5-[(1S)-1-(methoxymethoxy)ethyl]-2,2-dimethyl-1,3-dioxolane

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 8h; Inert atmosphere;
DOI:10.1016/j.tetasy.2011.02.010

Reference yield:

: 1308324-61-9
C₂₅H₃₈O₉

: 1308324-49-3
(4S,5S)-4-[(1S,4R)-6-[(4-Methoxybenzyl)oxy]-1,4-di(methoxymethoxy)-2-hexynyl]-5-[(1S)-1-(methoxymethoxy)ethyl]-2,2-dimethyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 3 steps

1.1: Dess-Martin periodane / dichloromethane / 3 h / 0 °C / Inert atmosphere

2.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / dichloromethane / 3 h / -78 - 0 °C / Molecular sieve; Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 8 h / 0 - 20 °C / Inert atmosphere

With Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole; In dichloromethane;
DOI:10.1016/j.tetasy.2011.02.010

Reference yield:

: 1308324-59-5
(4S,5S)-4-[(benzyloxy)methyl]-5-[(1S)-1-(methoxymethoxy)ethyl]-2,2-dimethyl-1,3-dioxolane

: 1308324-49-3
(4S,5S)-4-[(1S,4R)-6-[(4-Methoxybenzyl)oxy]-1,4-di(methoxymethoxy)-2-hexynyl]-5-[(1S)-1-(methoxymethoxy)ethyl]-2,2-dimethyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 6 steps

1.1: ammonia; lithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

1.2: Inert atmosphere

2.1: dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane / 2 h / 20 °C / Cooling with ice; Inert atmosphere

3.1: ethylmagnesium bromide / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

3.2: 2 h / Reflux

4.1: Dess-Martin periodane / dichloromethane / 3 h / 0 °C / Inert atmosphere

5.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / dichloromethane / 3 h / -78 - 0 °C / Molecular sieve; Inert atmosphere

5.2: 0 - 20 °C / Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 8 h / 0 - 20 °C / Inert atmosphere

With ethylmagnesium bromide; ammonia; lithium; Dess-Martin periodane; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tetasy.2011.02.010