(1E,3S,4S,6S)-3-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]nona-1,8-dien-4-yl (2Z)4-{(2R,6R)-6-[(2S)-2-methylpent-4-yn-1-yl]-5,6-dihydro-2H-pyran-2-yl}but-2-enoate

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Chemical Name:(1E,3S,4S,6S)-3-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]nona-1,8-dien-4-yl (2Z)4-{(2R,6R)-6-[(2S)-2-methylpent-4-yn-1-yl]-5,6-dihydro-2H-pyran-2-yl}but-2-enoate
CAS No.:1379586-89-6
Molecular Formula:C₄₀H₅₄O₈
Molecular Weight:662.864
Hs Code.:

(1E,3S,4S,6S)-3-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]nona-1,8-dien-4-yl (2Z)4-{(2R,6R)-6-[(2S)-2-methylpent-4-yn-1-yl]-5,6-dihydro-2H-pyran-2-yl}but-2-enoate

Synonyms:(1E,3S,4S,6S)-3-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]nona-1,8-dien-4-yl (2Z)4-{(2R,6R)-6-[(2S)-2-methylpent-4-yn-1-yl]-5,6-dihydro-2H-pyran-2-yl}but-2-enoate

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Chemical Property of (1E,3S,4S,6S)-3-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]nona-1,8-dien-4-yl (2Z)4-{(2R,6R)-6-[(2S)-2-methylpent-4-yn-1-yl]-5,6-dihydro-2H-pyran-2-yl}but-2-enoate

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Technology Process of (1E,3S,4S,6S)-3-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]nona-1,8-dien-4-yl (2Z)4-{(2R,6R)-6-[(2S)-2-methylpent-4-yn-1-yl]-5,6-dihydro-2H-pyran-2-yl}but-2-enoate

There total 10 articles about (1E,3S,4S,6S)-3-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]nona-1,8-dien-4-yl (2Z)4-{(2R,6R)-6-[(2S)-2-methylpent-4-yn-1-yl]-5,6-dihydro-2H-pyran-2-yl}but-2-enoate 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:

: 1379586-87-4
(1E,3S,4S,6S)-3-(4-methoxybenzyloxy)-6-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]nona-1,8-dien-4-ol

: 1379586-89-6
(1E,3S,4S,6S)-3-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]nona-1,8-dien-4-yl (2Z)4-{(2R,6R)-6-[(2S)-2-methylpent-4-yn-1-yl]-5,6-dihydro-2H-pyran-2-yl}but-2-enoate

: 1379586-96-5
(1E,3S,4S,6S)-3-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]nona-1,8-dien-4-yl (2E)4-{(2R,6R)-6-[(2S)-2-methylpent-4-yn-1-yl]-5,6-dihydro-2H-pyran-2-yl}but-2-enoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

1.2: 2 h / 20 °C / Inert atmosphere

2.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran / 1.17 h / -78 °C / Inert atmosphere

With 18-crown-6 ether; 2,4,6-trichlorobenzoyl chloride; potassium hexamethylsilazane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 2.1: Still-Gennari olefination;
DOI:10.1002/chem.201102899

Reference yield:

: 936552-51-1
(S)-3-(methoxymethoxy)hex-5-enal

: 1379586-89-6
(1E,3S,4S,6S)-3-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]nona-1,8-dien-4-yl (2Z)4-{(2R,6R)-6-[(2S)-2-methylpent-4-yn-1-yl]-5,6-dihydro-2H-pyran-2-yl}but-2-enoate

: 1379586-96-5
(1E,3S,4S,6S)-3-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]nona-1,8-dien-4-yl (2E)4-{(2R,6R)-6-[(2S)-2-methylpent-4-yn-1-yl]-5,6-dihydro-2H-pyran-2-yl}but-2-enoate

Guidance literature:: Multi-step reaction with 8 steps

1.1: (R,R)-(-)-2,6-bis[2-(hydroxyldiphenylmethyl)-1-pyrrolidinyl-methyl]-4-methylphenole; diethylzinc / tetrahydrofuran; hexane / 12 h / 20 °C / Inert atmosphere; Molecular sieve

2.1: camphor-10-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere

3.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

4.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 20 °C

5.1: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 12 h / -35 - 20 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / dichloromethane / -78 - 0 °C / Inert atmosphere

7.1: 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

7.2: 2 h / 20 °C / Inert atmosphere

8.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran / 1.17 h / -78 °C / Inert atmosphere

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; 18-crown-6 ether; (R,R)-(-)-2,6-bis[2-(hydroxyldiphenylmethyl)-1-pyrrolidinyl-methyl]-4-methylphenole; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; diethylzinc; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Aldol reaction / 8.1: Still-Gennari olefination;
DOI:10.1002/chem.201102899

Reference yield:

: 1379586-92-1
(S)-2-[2-(methoxymethoxy)pent-4-enyl]-1,3-dithiane

: 1379586-89-6
(1E,3S,4S,6S)-3-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]nona-1,8-dien-4-yl (2Z)4-{(2R,6R)-6-[(2S)-2-methylpent-4-yn-1-yl]-5,6-dihydro-2H-pyran-2-yl}but-2-enoate

: 1379586-96-5
(1E,3S,4S,6S)-3-[(4-methoxybenzyl)oxy]-6-(methoxymethoxy)-1-[(2S)-4-methyl-3,6-dihydro-2H-pyran-2-yl]nona-1,8-dien-4-yl (2E)4-{(2R,6R)-6-[(2S)-2-methylpent-4-yn-1-yl]-5,6-dihydro-2H-pyran-2-yl}but-2-enoate

Guidance literature:: Multi-step reaction with 9 steps

1.1: water; calcium carbonate; methyl iodide / acetonitrile / 45 °C / Inert atmosphere

2.1: (R,R)-(-)-2,6-bis[2-(hydroxyldiphenylmethyl)-1-pyrrolidinyl-methyl]-4-methylphenole; diethylzinc / tetrahydrofuran; hexane / 12 h / 20 °C / Inert atmosphere; Molecular sieve

3.1: camphor-10-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere

4.1: sodium tetrahydroborate / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

5.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 20 °C

6.1: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 12 h / -35 - 20 °C / Inert atmosphere

7.1: diisobutylaluminium hydride / dichloromethane / -78 - 0 °C / Inert atmosphere

8.1: 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

8.2: 2 h / 20 °C / Inert atmosphere

9.1: 18-crown-6 ether; potassium hexamethylsilazane / tetrahydrofuran / 1.17 h / -78 °C / Inert atmosphere

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; 18-crown-6 ether; (R,R)-(-)-2,6-bis[2-(hydroxyldiphenylmethyl)-1-pyrrolidinyl-methyl]-4-methylphenole; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; water; diethylzinc; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; calcium carbonate; lithium hexamethyldisilazane; methyl iodide; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 2.1: Aldol reaction / 9.1: Still-Gennari olefination;
DOI:10.1002/chem.201102899