2-[(2E,6Z,4R)-6-(2-benzyloxymethoxyethyl)-1,1-dimethyl-4-triethylsilyloxy-8-tri-isopropylsilyloxyocta-2,6-dien-1-yl]-2-[(2E)-but-2-enyl]-1,3-dithiane

Base Information

Chemical Name:2-[(2E,6Z,4R)-6-(2-benzyloxymethoxyethyl)-1,1-dimethyl-4-triethylsilyloxy-8-tri-isopropylsilyloxyocta-2,6-dien-1-yl]-2-[(2E)-but-2-enyl]-1,3-dithiane
CAS No.:1083348-87-1
Molecular Formula:C₄₃H₇₆O₄S₂Si₂
Molecular Weight:777.377
Hs Code.:

Synonyms:2-[(2E,6Z,4R)-6-(2-benzyloxymethoxyethyl)-1,1-dimethyl-4-triethylsilyloxy-8-tri-isopropylsilyloxyocta-2,6-dien-1-yl]-2-[(2E)-but-2-enyl]-1,3-dithiane

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Chemical Property of 2-[(2E,6Z,4R)-6-(2-benzyloxymethoxyethyl)-1,1-dimethyl-4-triethylsilyloxy-8-tri-isopropylsilyloxyocta-2,6-dien-1-yl]-2-[(2E)-but-2-enyl]-1,3-dithiane

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Technology Process of 2-[(2E,6Z,4R)-6-(2-benzyloxymethoxyethyl)-1,1-dimethyl-4-triethylsilyloxy-8-tri-isopropylsilyloxyocta-2,6-dien-1-yl]-2-[(2E)-but-2-enyl]-1,3-dithiane

There total 20 articles about 2-[(2E,6Z,4R)-6-(2-benzyloxymethoxyethyl)-1,1-dimethyl-4-triethylsilyloxy-8-tri-isopropylsilyloxyocta-2,6-dien-1-yl]-2-[(2E)-but-2-enyl]-1,3-dithiane 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: 70.0%

: 1083349-15-8
(1RS,2RS)-2-[(2E,6Z,4R)-6-(2-Benzyloxymethoxyethyl)-1,1-dimethyl-4-triethylsilyloxy-8-triisopropylsilyloxyocta-2,6-dien-1-yl]-2-[(2E)-but-2-enyl]-1,3-dithiane-1-oxide

: 1083348-87-1
2-[(2E,6Z,4R)-6-(2-benzyloxymethoxyethyl)-1,1-dimethyl-4-triethylsilyloxy-8-tri-isopropylsilyloxyocta-2,6-dien-1-yl]-2-[(2E)-but-2-enyl]-1,3-dithiane

Guidance literature:: With diphosphorus tetraiodide; triethylamine; In dichloromethane; at 0 ℃; for 0.666667h; Darkness;
DOI:10.1016/j.tetlet.2008.08.075

Reference yield: 35.0%

: 4784-77-4,39616-19-8,29576-14-5
(E)-1-Bromo-2-butene

: 1083348-85-9
2-[(2E,6Z,4R)-6-(2-benzyloxymethoxyethyl)-1,1-dimethyl-4-triethylsilyloxy-8-triisopropylsilyloxyocta-2,6-dienyl]-1,3-dithiane

: 1083348-87-1
2-[(2E,6Z,4R)-6-(2-benzyloxymethoxyethyl)-1,1-dimethyl-4-triethylsilyloxy-8-tri-isopropylsilyloxyocta-2,6-dien-1-yl]-2-[(2E)-but-2-enyl]-1,3-dithiane

Guidance literature:: 2-[(2E,6Z,4R)-6-(2-benzyloxymethoxyethyl)-1,1-dimethyl-4-triethylsilyloxy-8-triisopropylsilyloxyocta-2,6-dienyl]-1,3-dithiane; With lithium diisopropyl amide; In tetrahydrofuran; at -78 - -60 ℃;

(E)-1-Bromo-2-butene; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1016/j.tetlet.2008.08.075

Reference yield:

: 1083348-83-7
(2Z)-methyl 3-[(2R)-3-(4-methoxybenzyloxy)-2-triethylsilyloxypropyl]hexa-2,5-dienoate

: 1083348-87-1
2-[(2E,6Z,4R)-6-(2-benzyloxymethoxyethyl)-1,1-dimethyl-4-triethylsilyloxy-8-tri-isopropylsilyloxyocta-2,6-dien-1-yl]-2-[(2E)-but-2-enyl]-1,3-dithiane

Guidance literature:: Multi-step reaction with 11 steps

1.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone; tert-butyl alcohol / 4 h / 20 °C

2.1: sodium periodate / methanol; tetrahydrofuran / 0 °C

2.2: 1 h / Cooling

3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0 - 20 °C

4.1: diisobutylaluminium hydride / methanol; n-heptane; toluene / -78 - 0 °C

4.2: 1 h / 20 °C

5.1: 1H-imidazole / dichloromethane / 20 °C

6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; aq. phosphate buffer / 0 - 10 °C / pH 7

7.1: pyridine; Dess-Martin periodane / dichloromethane

8.1: lithium hexamethyldisilazane / tetrahydrofuran; toluene / 0.33 h / -78 °C

8.2: 1 h / -78 - 20 °C

9.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C

10.1: lithium diisopropyl amide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran; n-heptane; ethylbenzene / 0.5 h / -78 °C

10.2: -78 - 20 °C

11.1: triethylamine; diphosphorous tetraiodide / dichloromethane / 0.67 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; osmium(VIII) oxide; diphosphorous tetraiodide; diisobutylaluminium hydride; Dess-Martin periodane; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; methanol; aq. phosphate buffer; n-heptane; dichloromethane; ethylbenzene; water; acetone; toluene; tert-butyl alcohol;
DOI:10.1039/c7ob02127e