dimethyl 3-((2S,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyltetrahydro-2H-pyran-2-yl)-2-oxopropylphosphonate

Base Information

Chemical Name:dimethyl 3-((2S,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyltetrahydro-2H-pyran-2-yl)-2-oxopropylphosphonate
CAS No.:1275506-46-1
Molecular Formula:C₂₄H₃₉O₈P
Molecular Weight:486.543
Hs Code.:

Synonyms:dimethyl 3-((2S,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyltetrahydro-2H-pyran-2-yl)-2-oxopropylphosphonate

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Chemical Property of dimethyl 3-((2S,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyltetrahydro-2H-pyran-2-yl)-2-oxopropylphosphonate

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Technology Process of dimethyl 3-((2S,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyltetrahydro-2H-pyran-2-yl)-2-oxopropylphosphonate

There total 14 articles about dimethyl 3-((2S,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyltetrahydro-2H-pyran-2-yl)-2-oxopropylphosphonate 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: 92.0%

: 1275506-45-0
methyl 2-((2S,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyltetrahydro-2H-pyran-2-yl)acetate

: 756-79-6
dimethyl methane phosphonate

: 1275506-46-1
dimethyl 3-((2S,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyltetrahydro-2H-pyran-2-yl)-2-oxopropylphosphonate

Guidance literature:: dimethyl methane phosphonate; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 1h; Inert atmosphere;

methyl 2-((2S,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyltetrahydro-2H-pyran-2-yl)acetate; In tetrahydrofuran; hexane; at -78 ℃; for 1h; Inert atmosphere;
DOI:10.1021/ol200223q

Reference yield:

: 1275506-31-4
(R)-1-methoxy-4-((3-methoxyhex-5-enyloxy)methyl)benzene

: 1275506-46-1
dimethyl 3-((2S,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyltetrahydro-2H-pyran-2-yl)-2-oxopropylphosphonate

Guidance literature:: Multi-step reaction with 12 steps

1.1: Hoveyda-Grubbs catalyst / dichloromethane / 3 h / 20 °C / Inert atmosphere

2.1: α,α-diphenyl-2-pyrrolidinemethanol trimethylsilyl ether; dihydrogen peroxide / dichloromethane / 2 h / 20 °C

3.1: dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

4.1: dichloromethane; toluene / 0.17 h / -40 °C / Inert atmosphere

4.2: 3 h / -40 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane / 0.58 h / -78 °C / Inert atmosphere

6.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

7.1: iodine / tetrahydrofuran / 0.75 h / 0 - 20 °C / Inert atmosphere

8.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water; toluene / 3 h / 20 °C / Darkness

9.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / tetrahydrofuran; water; tert-butyl alcohol / 3 h / 0 - 20 °C

10.1: diethyl ether / 0.17 h / 0 °C / Inert atmosphere

11.1: palladium on carbon; hydrogen; triethylamine / toluene / 1 h / 20 °C

12.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere

12.2: 1 h / -78 °C / Inert atmosphere

With 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; n-butyllithium; 2-methyl-but-2-ene; [bis(acetoxy)iodo]benzene; α,α-diphenyl-2-pyrrolidinemethanol trimethylsilyl ether; palladium on carbon; hydrogen; dihydrogen peroxide; iodine; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; dichloromethane; water; toluene; tert-butyl alcohol; 9.1: Pinnick reaction;
DOI:10.1021/ol200223q

Reference yield:

: 1219715-13-5
(2R,3S,6R)-6-allyl-2-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-3-methyl-3,6-dihydro-2H-pyran

: 1275506-46-1
dimethyl 3-((2S,5S,6R)-6-((S)-2-methoxy-4-(4-methoxybenzyloxy)butyl)-5-methyltetrahydro-2H-pyran-2-yl)-2-oxopropylphosphonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water; toluene / 3 h / 20 °C / Darkness

2.1: sodium dihydrogenphosphate; sodium chlorite; 2-methyl-but-2-ene / tetrahydrofuran; water; tert-butyl alcohol / 3 h / 0 - 20 °C

3.1: diethyl ether / 0.17 h / 0 °C / Inert atmosphere

4.1: palladium on carbon; hydrogen; triethylamine / toluene / 1 h / 20 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere

5.2: 1 h / -78 °C / Inert atmosphere

With 2,6-dimethylpyridine; sodium chlorite; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; n-butyllithium; 2-methyl-but-2-ene; palladium on carbon; hydrogen; triethylamine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; water; toluene; tert-butyl alcohol; 2.1: Pinnick reaction;
DOI:10.1021/ol200223q