(2E,4Z,6S,7S,8E,10S,11R,12S,14R)-11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoic acid

Base Information

Chemical Name:(2E,4Z,6S,7S,8E,10S,11R,12S,14R)-11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoic acid
CAS No.:1402167-78-5
Molecular Formula:C₄₇H₇₃NO₁₁Si
Molecular Weight:856.182
Hs Code.:

(2E,4Z,6S,7S,8E,10S,11R,12S,14R)-11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoic acid

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Chemical Property of (2E,4Z,6S,7S,8E,10S,11R,12S,14R)-11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoic acid

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Technology Process of (2E,4Z,6S,7S,8E,10S,11R,12S,14R)-11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoic acid

There total 25 articles about (2E,4Z,6S,7S,8E,10S,11R,12S,14R)-11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoic acid 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:

: 1402167-77-4
(2E,4Z,6S,7S,8E,10S,11R,12S,14R)-11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienal

: 1402167-78-5
(2E,4Z,6S,7S,8E,10S,11R,12S,14R)-11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoic acid

Guidance literature:: With potassium dihydrogenphosphate; 2-methyl-but-2-ene; sodium perchlorate; In water; tert-butyl alcohol; at 20 ℃; for 12h;
DOI:10.1002/chem.201201600

Reference yield:

: 1118756-81-2
C₂₄H₄₀O₅

: 1402167-78-5
(2E,4Z,6S,7S,8E,10S,11R,12S,14R)-11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoic acid

Guidance literature:: Multi-step reaction with 11 steps

1: potassium hydride / tetrahydrofuran; mineral oil / 16 h / 0 - 20 °C

2: osmium(VIII) oxide; 4-methylmorpholine N-oxide / dichloromethane; water / 16 h / 20 °C

3: sodium periodate / water; acetone / 1 h / 20 °C

4: samarium diiodide / tetrahydrofuran / 1 h / -78 °C

5: Martins sulfurane / dichloromethane / 1 h / 0 °C

6: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 0.25 h / -30 °C

7: 1H-imidazole / N,N-dimethyl-formamide / 16 h

8: copper(II) nitrate / acetic anhydride / 2.25 h / 0 °C

9: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 12 h / 20 °C

10: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C

11: potassium dihydrogenphosphate; 2-methyl-but-2-ene; sodium perchlorate / water; tert-butyl alcohol / 12 h / 20 °C

With pyridine; 1H-imidazole; sodium periodate; potassium dihydrogenphosphate; osmium(VIII) oxide; samarium diiodide; 2-methyl-but-2-ene; Martins sulfurane; dimethylsulfide borane complex; sodium perchlorate; potassium hydride; sodium hydrogencarbonate; Dess-Martin periodane; copper(II) nitrate; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; water; acetic anhydride; N,N-dimethyl-formamide; acetone; toluene; mineral oil; tert-butyl alcohol; 4: Reformatsky-type reaction;
DOI:10.1002/chem.201201600

Reference yield:

: 1402167-29-6
(S,2E,4Z)-methyl 7-(tert-butyldimethylsilyloxy)-6-hydroxy-2-methylhepta-2,4-dienoate

: 1402167-78-5
(2E,4Z,6S,7S,8E,10S,11R,12S,14R)-11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoic acid

Guidance literature:: Multi-step reaction with 15 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / -20 °C

2.1: diisobutylaluminium hydride / tetrahydrofuran; cyclohexane / 3 h / -78 - -20 °C

3.1: 1H-imidazole / dichloromethane / 0.25 h / -20 °C

4.1: camphor-10-sulfonic acid / methanol; dichloromethane / 2 h / 0 °C

5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 3 h / 85 °C

6.1: isopropylmagnesium chloride / tetrahydrofuran / 0.5 h / -78 °C

6.2: 2 h / -78 °C

7.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 3 h / 20 °C

8.1: samarium diiodide / tetrahydrofuran / 1.5 h / -78 °C

9.1: Martins sulfurane / dichloromethane / 1 h / 0 °C

10.1: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 0.25 h / -30 °C

11.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h

12.1: copper(II) nitrate / acetic anhydride / 2.25 h / 0 °C

13.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 12 h / 20 °C

14.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C

15.1: potassium dihydrogenphosphate; 2-methyl-but-2-ene; sodium perchlorate / water; tert-butyl alcohol / 12 h / 20 °C

With pyridine; 1H-imidazole; potassium dihydrogenphosphate; samarium diiodide; 2-methyl-but-2-ene; Martins sulfurane; dimethylsulfide borane complex; camphor-10-sulfonic acid; sodium perchlorate; isopropylmagnesium chloride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; copper(II) nitrate; pyridine hydrogenfluoride; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; water; acetic anhydride; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; tert-butyl alcohol;
DOI:10.1002/chem.201201600