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

Base Information

• Chemical Name: (2E,4Z,6S,7R,8E,10S,11R,12S,14R)-methyl 11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate
• CAS No.: 1402167-45-6
• Molecular Formula: C₄₈H₇₅NO₁₁Si
• Molecular Weight: 870.209

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

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

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

C24H40O5 (1118756-81-2) → (2E,4Z,6S,7R,8E,10S,11R,12S,14R)-methyl 11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate (1402167-45-6)

Guidance literature:

Multi-step reaction with 12 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: L-Selectride / tetrahydrofuran / 0.5 h / -78 °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

12: methanol; hexane; toluene / 0.5 h / 20 °C

With pyridine; 1H-imidazole; sodium periodate; potassium dihydrogenphosphate; osmium(VIII) oxide; samarium diiodide; 2-methyl-but-2-ene; Martins sulfurane; sodium perchlorate; potassium hydride; L-Selectride; sodium hydrogencarbonate; Dess-Martin periodane; copper(II) nitrate; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; hexane; 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:

(S,2E,4Z)-methyl 7-(tert-butyldimethylsilyloxy)-6-methoxy-2-methylhepta-2,4-dienoate (1402167-30-9) → (2E,4Z,6S,7R,8E,10S,11R,12S,14R)-methyl 11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate (1402167-45-6)

Guidance literature:

Multi-step reaction with 15 steps

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

2.1: 1H-imidazole / dichloromethane / 0.25 h / -20 °C

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

4.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 3 h / 85 °C

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

5.2: 2 h / -78 °C

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

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

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

9.1: L-Selectride / tetrahydrofuran / 0.5 h / -78 °C

10.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h

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

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

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

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

15.1: methanol; hexane; toluene / 0.5 h / 20 °C

With pyridine; 1H-imidazole; potassium dihydrogenphosphate; samarium diiodide; 2-methyl-but-2-ene; Martins sulfurane; camphor-10-sulfonic acid; sodium perchlorate; isopropylmagnesium chloride; L-Selectride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; copper(II) nitrate; pyridine hydrogenfluoride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; hexane; dichloromethane; cyclohexane; water; acetic anhydride; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol;

DOI:10.1002/chem.201201600

Reference yield:

(S,2E,4Z)-methyl 7-(tert-butyldimethylsilyloxy)-6-hydroxy-2-methylhepta-2,4-dienoate (1402167-29-6) → (2E,4Z,6S,7R,8E,10S,11R,12S,14R)-methyl 11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trienoate (1402167-45-6)

Guidance literature:

Multi-step reaction with 16 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: L-Selectride / tetrahydrofuran / 0.5 h / -78 °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

16.1: methanol; hexane; toluene / 0.5 h / 20 °C

With pyridine; 1H-imidazole; potassium dihydrogenphosphate; samarium diiodide; 2-methyl-but-2-ene; Martins sulfurane; camphor-10-sulfonic acid; sodium perchlorate; isopropylmagnesium chloride; L-Selectride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; copper(II) nitrate; pyridine hydrogenfluoride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; hexane; dichloromethane; cyclohexane; water; acetic anhydride; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; tert-butyl alcohol;

DOI:10.1002/chem.201201600

upstream raw materials:

C₂₄H₄₀O₅

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

(S,2E,4Z)-methyl 7-(tert-butyldimethylsilyloxy)-6-methoxy-2-methylhepta-2,4-dienoate

(S,2E,4Z)-7-(tert-butyldimethylsilyloxy)-6-methoxy-2-methylhepta-2,4-dien-1-ol

Downstream raw materials:

C₄₈H₇₇NO₉Si

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