(2Z,4E,6R,7S,8S,10E,12E,14S)-methyl 14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-7-(formyloxy)-2,14-dimethoxy-4,6,8,10-tetramethyltetradeca-2,4,10,12-tetraenoate

Base Information

• Chemical Name: (2Z,4E,6R,7S,8S,10E,12E,14S)-methyl 14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-7-(formyloxy)-2,14-dimethoxy-4,6,8,10-tetramethyltetradeca-2,4,10,12-tetraenoate
• CAS No.: 1132970-13-8
• Molecular Formula: C₄₉H₇₂O₉Si
• Molecular Weight: 833.191
• Mol file: 1132970-13-8.mol

Synonyms:(2Z,4E,6R,7S,8S,10E,12E,14S)-methyl 14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-7-(formyloxy)-2,14-dimethoxy-4,6,8,10-tetramethyltetradeca-2,4,10,12-tetraenoate

Chemical Property of (2Z,4E,6R,7S,8S,10E,12E,14S)-methyl 14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-7-(formyloxy)-2,14-dimethoxy-4,6,8,10-tetramethyltetradeca-2,4,10,12-tetraenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2Z,4E,6R,7S,8S,10E,12E,14S)-methyl 14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-7-(formyloxy)-2,14-dimethoxy-4,6,8,10-tetramethyltetradeca-2,4,10,12-tetraenoate

There total 27 articles about (2Z,4E,6R,7S,8S,10E,12E,14S)-methyl 14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-7-(formyloxy)-2,14-dimethoxy-4,6,8,10-tetramethyltetradeca-2,4,10,12-tetraenoate 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: 99.0%

(2Z,4E,6R,7S,8S,10E,12E,14S)-methyl 14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-7-hydroxy-2,14-dimethoxy-4,6,8,10-tetramethyltetradeca-2,4,10,12-tetraenoate (1132970-12-7) + formyl acetic anhydride (2258-42-6) → (2Z,4E,6R,7S,8S,10E,12E,14S)-methyl 14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-7-(formyloxy)-2,14-dimethoxy-4,6,8,10-tetramethyltetradeca-2,4,10,12-tetraenoate (1132970-13-8)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 0.25h; Inert atmosphere;

DOI:10.1002/anie.200804645

Reference yield:

(R)-4-benzyl-3-((2R,3S)-3-(tert-butyldiphenylsilyloxy)-2-methylbutanoyl)oxazolidin-2-one (1379802-66-0) → (2Z,4E,6R,7S,8S,10E,12E,14S)-methyl 14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-7-(formyloxy)-2,14-dimethoxy-4,6,8,10-tetramethyltetradeca-2,4,10,12-tetraenoate (1132970-13-8)

Guidance literature:

Multi-step reaction with 16 steps

1.1: lithium borohydride / tetrahydrofuran; diethyl ether; ethanol / 4.5 h / 0 - 20 °C / Inert atmosphere

2.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; potassium bromide / dichloromethane / 0 °C / pH 8.6 / aq. buffer

2.2: 0.42 h / 0 °C

3.1: hydroxylamine hydrochloride / pyridine; ethanol / 12.5 h / 20 °C / Inert atmosphere

4.1: dichloromethane / -78 °C / Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / methanol / 1.75 h / 20 °C / Inert atmosphere

6.1: pyridine / dichloromethane / 0.17 h / -78 - 0 °C / Inert atmosphere

7.1: hydrogen; boric acid / methanol; water / 3 h / 20 °C

8.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 118 h / -10 - -5 °C / Inert atmosphere

9.1: toluene-4-sulfonic acid / 0.33 h / 20 °C / Inert atmosphere

10.1: lithium hydroxide / tetrahydrofuran; methanol; water / 0.42 h / 20 °C

11.1: sodium periodate / chloroform / 0.47 h / 20 °C / Inert atmosphere

12.1: (-)-N-methylephedrine; zinc trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / toluene / 35 h / 20 °C / Inert atmosphere

12.2: 17 h / 20 °C / Inert atmosphere

13.1: tris(acetonitrile)pentamethylcyclopentadienyl-ruthenium(I) hexafluorophosphate; Triethoxysilane / dichloromethane / 0 - 20 °C / Inert atmosphere

13.2: 0 - 20 °C / Inert atmosphere

14.1: tetrahydrofuran; N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

15.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

16.1: dmap / dichloromethane / 20 °C / Inert atmosphere

16.2: 0.25 h / 20 °C / Inert atmosphere

With pyridine; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium periodate; lithium borohydride; Triethoxysilane; tris(acetonitrile)pentamethylcyclopentadienyl-ruthenium(I) hexafluorophosphate; (-)-N-methylephedrine; hydroxylamine hydrochloride; hydrogen; boric acid; zinc trifluoromethanesulfonate; toluene-4-sulfonic acid; pyridine hydrogenfluoride; acetic acid; N-ethyl-N,N-diisopropylamine; potassium bromide; lithium hydroxide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1002/chem.201102797

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (2Z,4E,6R,7S,8S,10E,12E,14S)-methyl 14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-7-(formyloxy)-2,14-dimethoxy-4,6,8,10-tetramethyltetradeca-2,4,10,12-tetraenoate (1132970-13-8)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 44 h / 20 °C / Inert atmosphere

2.1: lithium borohydride / tetrahydrofuran; diethyl ether; ethanol / 4.5 h / 0 - 20 °C / Inert atmosphere

3.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; potassium bromide / dichloromethane / 0 °C / pH 8.6 / aq. buffer

3.2: 0.42 h / 0 °C

4.1: hydroxylamine hydrochloride / pyridine; ethanol / 12.5 h / 20 °C / Inert atmosphere

5.1: dichloromethane / -78 °C / Inert atmosphere

5.2: 0 - 20 °C / Inert atmosphere

6.1: toluene-4-sulfonic acid / methanol / 1.75 h / 20 °C / Inert atmosphere

7.1: pyridine / dichloromethane / 0.17 h / -78 - 0 °C / Inert atmosphere

8.1: hydrogen; boric acid / methanol; water / 3 h / 20 °C

9.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 118 h / -10 - -5 °C / Inert atmosphere

10.1: toluene-4-sulfonic acid / 0.33 h / 20 °C / Inert atmosphere

11.1: lithium hydroxide / tetrahydrofuran; methanol; water / 0.42 h / 20 °C

12.1: sodium periodate / chloroform / 0.47 h / 20 °C / Inert atmosphere

13.1: (-)-N-methylephedrine; zinc trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / toluene / 35 h / 20 °C / Inert atmosphere

13.2: 17 h / 20 °C / Inert atmosphere

14.1: tris(acetonitrile)pentamethylcyclopentadienyl-ruthenium(I) hexafluorophosphate; Triethoxysilane / dichloromethane / 0 - 20 °C / Inert atmosphere

14.2: 0 - 20 °C / Inert atmosphere

15.1: tetrahydrofuran; N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

16.1: pyridine hydrogenfluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

17.1: dmap / dichloromethane / 20 °C / Inert atmosphere

17.2: 0.25 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium periodate; lithium borohydride; Triethoxysilane; tris(acetonitrile)pentamethylcyclopentadienyl-ruthenium(I) hexafluorophosphate; (-)-N-methylephedrine; hydroxylamine hydrochloride; hydrogen; boric acid; zinc trifluoromethanesulfonate; toluene-4-sulfonic acid; pyridine hydrogenfluoride; acetic acid; N-ethyl-N,N-diisopropylamine; potassium bromide; lithium hydroxide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1002/chem.201102797

upstream raw materials:

(2Z,4E,6R,7S,8S,10E,12E,14S)-methyl 14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-7-hydroxy-2,14-dimethoxy-4,6,8,10-tetramethyltetradeca-2,4,10,12-tetraenoate

formyl acetic anhydride

(2S,4E)-2,4-dimethyl-5-iodo-4-pentenal

C₄₁H₅₈INO₅SSi

Downstream raw materials:

methyl (2Z,4E,6R,7S,8S,10E,12E,14S,15R,16S,17R,18S,19S)-19-(tert-butyldiphenylsilyloxy)-7,15,17-trihydroxy-2,14-dimethoxy-4,6,8,10,16,18-hexamethylicosa-2,4,10,12-tetraenoate

(2Z,4E,6R,7S,8S,10E,12E,14S)-methyl 14-((4R,5S,6R)-6-((2S,3S)-3-(tert-butyldiphenylsilyloxy)butan-2-yl)-2,2,5-trimethyl-1,3-dioxan-4-yl)-7-hydroxy-2,14-dimethoxy-4,6,8,10-tetramethyltetradeca-2,4,10,12-tetraenoate

(3Z,5E,7R,8S,9S,11E,13E,15S,16R)-16-((2S,3R,4S,5S)-5-(tert-butyldiphenylsilyloxy)-3-hydroxy-4-methylhexan-2-yl)-8-hydroxy-3,15-dimethoxy-5,7,9,11-tetramethyloxacyclohexadeca-3,5,11,13-tetraen-2-one

(2Z,4E,6R,7S,8S,10E,12E,14S,15R,16S,17R,18S,19S)-methyl 19-(tert-butyldiphenylsilyloxy)-7-(formyloxy)-15,17-dihydroxy-2,14-dimethoxy-4,6,8,10,16,18-hexamethylicosa-2,4,10,12-tetraenoate

Refernces

• 1、 Kleinbeck, Florian,Carreira, Erick M.. "Total synthesis of bafilomycin A1". supporting information; experimental part. p. 578 - 581. Retrieved 2009/04/14.