3-(2-benzyloxy-benzyl)-5-[7-benzyloxy-3-(tert-butyldiphenylsilanyloxymethyl)-3,8-dimethoxy-isochroman-6-yl]-4,5-dihydroisoxazole

Base Information

• Chemical Name: 3-(2-benzyloxy-benzyl)-5-[7-benzyloxy-3-(tert-butyldiphenylsilanyloxymethyl)-3,8-dimethoxy-isochroman-6-yl]-4,5-dihydroisoxazole
• CAS No.: 1315341-13-9
• Molecular Formula: C₅₂H₅₅NO₇Si
• Molecular Weight: 834.097
• Mol file: 1315341-13-9.mol

Synonyms:3-(2-benzyloxy-benzyl)-5-[7-benzyloxy-3-(tert-butyldiphenylsilanyloxymethyl)-3,8-dimethoxy-isochroman-6-yl]-4,5-dihydroisoxazole

Chemical Property of 3-(2-benzyloxy-benzyl)-5-[7-benzyloxy-3-(tert-butyldiphenylsilanyloxymethyl)-3,8-dimethoxy-isochroman-6-yl]-4,5-dihydroisoxazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2-benzyloxy-benzyl)-5-[7-benzyloxy-3-(tert-butyldiphenylsilanyloxymethyl)-3,8-dimethoxy-isochroman-6-yl]-4,5-dihydroisoxazole

There total 17 articles about 3-(2-benzyloxy-benzyl)-5-[7-benzyloxy-3-(tert-butyldiphenylsilanyloxymethyl)-3,8-dimethoxy-isochroman-6-yl]-4,5-dihydroisoxazole 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: 89.0%

1-Benzyloxy-2-(2-nitro-ethyl)-benzene (908292-04-6) + (7-benzyloxy-3,8-dimethoxy-6-vinyl-isochroman-3-ylmethoxy)-tert-butyldiphenylsilane (1315341-01-5) → 3-(2-benzyloxy-benzyl)-5-[7-benzyloxy-3-(tert-butyldiphenylsilanyloxymethyl)-3,8-dimethoxy-isochroman-6-yl]-4,5-dihydroisoxazole (1315341-13-9)

Guidance literature:

With phenyl isocyanate; triethylamine; In benzene; at 20 ℃; for 18h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/jo200398v

Reference yield:

acetic acid 2-acetoxy-5-bromo-4-formyl-3-methoxybenzyl ester (1315341-03-7) → 3-(2-benzyloxy-benzyl)-5-[7-benzyloxy-3-(tert-butyldiphenylsilanyloxymethyl)-3,8-dimethoxy-isochroman-6-yl]-4,5-dihydroisoxazole (1315341-13-9)

Guidance literature:

Multi-step reaction with 13 steps

1.1: water; sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

2.1: potassium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C / Inert atmosphere

2.2: 17 h / 20 °C / Inert atmosphere

3.1: sodium tetrahydroborate / methanol / 12 h / 20 °C

4.1: pyridine / dichloromethane / 120 h / 20 °C

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 18 h / 115 - 120 °C / Inert atmosphere

6.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 12 h / 20 °C

7.1: 1H-imidazole / N,N-dimethyl-formamide / 2.5 h / 20 °C / Inert atmosphere

8.1: Dess-Martin periodane / dichloromethane / 12 h / 20 °C / Inert atmosphere

9.1: potassium carbonate / 4 h / 0 °C / Inert atmosphere

10.1: pyridinium p-toluenesulfonate / 42 h / 20 °C / Inert atmosphere

11.1: Dess-Martin periodane / dichloromethane / 20 h / 1 °C / Inert atmosphere

12.1: tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

13.1: phenyl isocyanate; triethylamine / benzene / 18 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; sodium tetrahydroborate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; water; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; phenyl isocyanate; 4-methylmorpholine N-oxide; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; benzene; 5.1: Stille coupling / 12.1: Wittig reaction;

DOI:10.1021/jo200398v

Reference yield:

6-bromo-3-hydroxy-2-methoxy-4-(morpholin-4-ylmethyl)benzaldehyde (1315341-21-9) → 3-(2-benzyloxy-benzyl)-5-[7-benzyloxy-3-(tert-butyldiphenylsilanyloxymethyl)-3,8-dimethoxy-isochroman-6-yl]-4,5-dihydroisoxazole (1315341-13-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 48 h / 20 °C

2.1: water; sodium hydroxide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

3.1: potassium carbonate / N,N-dimethyl-formamide / 0.25 h / 20 °C / Inert atmosphere

3.2: 17 h / 20 °C / Inert atmosphere

4.1: sodium tetrahydroborate / methanol / 12 h / 20 °C

5.1: pyridine / dichloromethane / 120 h / 20 °C

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 18 h / 115 - 120 °C / Inert atmosphere

7.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 12 h / 20 °C

8.1: 1H-imidazole / N,N-dimethyl-formamide / 2.5 h / 20 °C / Inert atmosphere

9.1: Dess-Martin periodane / dichloromethane / 12 h / 20 °C / Inert atmosphere

10.1: potassium carbonate / 4 h / 0 °C / Inert atmosphere

11.1: pyridinium p-toluenesulfonate / 42 h / 20 °C / Inert atmosphere

12.1: Dess-Martin periodane / dichloromethane / 20 h / 1 °C / Inert atmosphere

13.1: tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

14.1: phenyl isocyanate; triethylamine / benzene / 18 h / 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; sodium tetrahydroborate; osmium(VIII) oxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; water; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; phenyl isocyanate; 4-methylmorpholine N-oxide; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; benzene; 6.1: Stille coupling / 13.1: Wittig reaction;

DOI:10.1021/jo200398v

upstream raw materials:

1-Benzyloxy-2-(2-nitro-ethyl)-benzene

(7-benzyloxy-3,8-dimethoxy-6-vinyl-isochroman-3-ylmethoxy)-tert-butyldiphenylsilane

acetic acid 2-acetoxy-5-bromo-4-formyl-3-methoxybenzyl ester

6-bromo-3-hydroxy-2-methoxy-4-(morpholin-4-ylmethyl)benzaldehyde