(1R,4R,10R,12R,1E,5E,7E)-1-bromo-9-(tert-butyldimethylsilanyloxy)-10-(4-methoxybenzyloxy)-7-methyl-4,12,12,14-tetramethoxytetradeca-1,5,7-triene

Base Information

Chemical Name:(1R,4R,10R,12R,1E,5E,7E)-1-bromo-9-(tert-butyldimethylsilanyloxy)-10-(4-methoxybenzyloxy)-7-methyl-4,12,12,14-tetramethoxytetradeca-1,5,7-triene
CAS No.:552850-08-5
Molecular Formula:C₃₃H₅₅BrO₇Si
Molecular Weight:671.785
Hs Code.:

(1R,4R,10R,12R,1E,5E,7E)-1-bromo-9-(tert-butyldimethylsilanyloxy)-10-(4-methoxybenzyloxy)-7-methyl-4,12,12,14-tetramethoxytetradeca-1,5,7-triene

Synonyms:(1R,4R,10R,12R,1E,5E,7E)-1-bromo-9-(tert-butyldimethylsilanyloxy)-10-(4-methoxybenzyloxy)-7-methyl-4,12,12,14-tetramethoxytetradeca-1,5,7-triene

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Chemical Property of (1R,4R,10R,12R,1E,5E,7E)-1-bromo-9-(tert-butyldimethylsilanyloxy)-10-(4-methoxybenzyloxy)-7-methyl-4,12,12,14-tetramethoxytetradeca-1,5,7-triene

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Technology Process of (1R,4R,10R,12R,1E,5E,7E)-1-bromo-9-(tert-butyldimethylsilanyloxy)-10-(4-methoxybenzyloxy)-7-methyl-4,12,12,14-tetramethoxytetradeca-1,5,7-triene

There total 27 articles about (1R,4R,10R,12R,1E,5E,7E)-1-bromo-9-(tert-butyldimethylsilanyloxy)-10-(4-methoxybenzyloxy)-7-methyl-4,12,12,14-tetramethoxytetradeca-1,5,7-triene 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: 93.0%

: 213978-44-0
(4R,5R,7R)-4-(tert-butyl-dimethyl-silanyloxy)-7,9,9-trimethoxy-5-(4'-methoxy-benzyloxy)-2-methyl-non-(2E)-enal

: 296785-24-5
(4E)(2R)-1-(benzothiazol-2-ylsulfonyl)-5-bromo-2-(methoxy)-pent-4-ene

: 552850-08-5
(1R,4R,10R,12R,1E,5E,7E)-1-bromo-9-(tert-butyldimethylsilanyloxy)-10-(4-methoxybenzyloxy)-7-methyl-4,12,12,14-tetramethoxytetradeca-1,5,7-triene

Guidance literature:: With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃;
DOI:10.1002/anie.200390321

Reference yield:

: 58-86-6
D-xylose

: 552850-08-5
(1R,4R,10R,12R,1E,5E,7E)-1-bromo-9-(tert-butyldimethylsilanyloxy)-10-(4-methoxybenzyloxy)-7-methyl-4,12,12,14-tetramethoxytetradeca-1,5,7-triene

Guidance literature:: Multi-step reaction with 18 steps

1.1: aq. HCl / 2 h / 20 °C

2.1: H₂SO₄ / 16 h / 0 °C

3.1: 32.8 g / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 1 h / 20 °C

4.1: 90 percent / LiAlH₄ / tetrahydrofuran / 3 h / 20 °C

5.1: t-BuOK / tetrahydrofuran / 1 h / -20 °C

5.2: 98 percent / NBu₄I / tetrahydrofuran / 15 h / 20 °C

6.1: 91 percent / aq. CaCO₃; Hg(ClO₄)2 / tetrahydrofuran / 3 h / 20 °C

7.1: diethyl ether / 3 h / -78 °C

7.2: 4.69 g / aq. NaOH; H₂O₂ / diethyl ether / 2 h / Heating

8.1: t-BuOK / tetrahydrofuran / 0.5 h / -20 °C

8.2: 97 percent / tetrahydrofuran / 6 h / 20 °C

9.1: 88 percent / 10-camphorsulfonic acid / methanol / 6 h / 0 - 20 °C

10.1: 98 percent / Et₃N / CH₂Cl₂ / 1 h / 0 - 20 °C

11.1: NMO; aq. OsO₄ / acetone / 12 h / 20 °C

12.1: 6.2 g / aq. NaIO₄; silica / petroleum ether; CH₂Cl₂ / 3 h / 20 °C

13.1: 89 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 1 h / 20 °C

14.1: 95 percent / 2,6-di-tert-butylpyridine; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

15.1: 94 percent / benzene / 48 h / Heating

16.1: 89 percent / DIBALH / CH₂Cl₂; hexane / 3 h / -78 - 20 °C

17.1: 94 percent / 2,6-lutidine; Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

18.1: 93 percent / NaHMDS / tetrahydrofuran / 5 h / -78 - 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; 2,6-di-tert-butyl-pyridine; mercury(II) perchlorate; sulfuric acid; (1S)-10-camphorsulfonic acid; potassium tert-butylate; sodium hexamethyldisilazane; silica gel; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; calcium carbonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; acetone; Petroleum ether; benzene; 15.1: Wittig reaction / 18.1: Julia reaction;
DOI:10.1039/b308305e

Reference yield:

: 13263-74-6
D-xylose diethyl dithioacetal

: 552850-08-5
(1R,4R,10R,12R,1E,5E,7E)-1-bromo-9-(tert-butyldimethylsilanyloxy)-10-(4-methoxybenzyloxy)-7-methyl-4,12,12,14-tetramethoxytetradeca-1,5,7-triene

Guidance literature:: Multi-step reaction with 17 steps

1.1: H₂SO₄ / 16 h / 0 °C

2.1: 32.8 g / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 1 h / 20 °C

3.1: 90 percent / LiAlH₄ / tetrahydrofuran / 3 h / 20 °C

4.1: t-BuOK / tetrahydrofuran / 1 h / -20 °C

4.2: 98 percent / NBu₄I / tetrahydrofuran / 15 h / 20 °C

5.1: 91 percent / aq. CaCO₃; Hg(ClO₄)2 / tetrahydrofuran / 3 h / 20 °C

6.1: diethyl ether / 3 h / -78 °C

6.2: 4.69 g / aq. NaOH; H₂O₂ / diethyl ether / 2 h / Heating

7.1: t-BuOK / tetrahydrofuran / 0.5 h / -20 °C

7.2: 97 percent / tetrahydrofuran / 6 h / 20 °C

8.1: 88 percent / 10-camphorsulfonic acid / methanol / 6 h / 0 - 20 °C

9.1: 98 percent / Et₃N / CH₂Cl₂ / 1 h / 0 - 20 °C

10.1: NMO; aq. OsO₄ / acetone / 12 h / 20 °C

11.1: 6.2 g / aq. NaIO₄; silica / petroleum ether; CH₂Cl₂ / 3 h / 20 °C

12.1: 89 percent / 10-camphorsulfonic acid / CH₂Cl₂ / 1 h / 20 °C

13.1: 95 percent / 2,6-di-tert-butylpyridine; Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

14.1: 94 percent / benzene / 48 h / Heating

15.1: 89 percent / DIBALH / CH₂Cl₂; hexane / 3 h / -78 - 20 °C

16.1: 94 percent / 2,6-lutidine; Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

17.1: 93 percent / NaHMDS / tetrahydrofuran / 5 h / -78 - 20 °C

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; N-methyl-2-indolinone; 2,6-di-tert-butyl-pyridine; mercury(II) perchlorate; sulfuric acid; (1S)-10-camphorsulfonic acid; potassium tert-butylate; sodium hexamethyldisilazane; silica gel; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; calcium carbonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; acetone; Petroleum ether; benzene; 14.1: Wittig reaction / 17.1: Julia reaction;
DOI:10.1039/b308305e