Benzoic acid (R)-[(4R,5S,6R)-5-(tert-butyl-dimethyl-silanyloxy)-6-((E)-2-ethoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethoxycarbonyl-methyl ester

Base Information

• Chemical Name: Benzoic acid (R)-[(4R,5S,6R)-5-(tert-butyl-dimethyl-silanyloxy)-6-((E)-2-ethoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethoxycarbonyl-methyl ester
• CAS No.: 178939-18-9
• Molecular Formula: C₂₈H₄₂O₉Si
• Molecular Weight: 550.722
• Mol file: 178939-18-9.mol

Synonyms:Benzoic acid (R)-[(4R,5S,6R)-5-(tert-butyl-dimethyl-silanyloxy)-6-((E)-2-ethoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethoxycarbonyl-methyl ester

Chemical Property of Benzoic acid (R)-[(4R,5S,6R)-5-(tert-butyl-dimethyl-silanyloxy)-6-((E)-2-ethoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethoxycarbonyl-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (R)-[(4R,5S,6R)-5-(tert-butyl-dimethyl-silanyloxy)-6-((E)-2-ethoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethoxycarbonyl-methyl ester

There total 6 articles about Benzoic acid (R)-[(4R,5S,6R)-5-(tert-butyl-dimethyl-silanyloxy)-6-((E)-2-ethoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethoxycarbonyl-methyl ester 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: 90.0%

2,2-dimethoxy-propane (77-76-9) + (E)-(4R,5S,6R,7R)-7-Benzoyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dihydroxy-oct-2-enedioic acid diethyl ester (178939-04-3) → Benzoic acid (R)-[(4R,5S,6R)-5-(tert-butyl-dimethyl-silanyloxy)-6-((E)-2-ethoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethoxycarbonyl-methyl ester (178939-18-9)

Guidance literature:

With sulfuric acid; In N,N-dimethyl-formamide; for 24h;

DOI:10.1016/0040-4020(96)00357-2

Reference yield:

(4R,5R)-{5-[(E)-2''-ethoxycarbonyl-vinyl]-2',2'-dimethyl-[1',3']-dioxolan-4-yl}-(E)-acrylic acid ethyl ester (114473-50-6) → Benzoic acid (R)-[(4R,5S,6R)-5-(tert-butyl-dimethyl-silanyloxy)-6-((E)-2-ethoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethoxycarbonyl-methyl ester (178939-18-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / Et₂O*BF₃, 1,2-ethane dithiol / CH₂Cl₂ / 0.17 h

2: 90 percent / imidazole / dimethylformamide / 24 h

3: 83 percent / OsO₄, aq. N-methylmorpholine N-oxide / acetone / 4 h

4: 99 percent / pyridine, DMAP / 2 h / Ambient temperature

5: 68 percent / aq. HF / acetonitrile / 3 h / Ambient temperature

6: 90 percent / conc. H₂SO₄ / dimethylformamide / 24 h

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; sulfuric acid; boron trifluoride diethyl etherate; hydrogen fluoride; ethane-1,2-dithiol; 4-methylmorpholine N-oxide; In dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/0040-4020(96)00357-2

Reference yield:

diethyl 4,5-dihydroxy-2,6-octadienedioate (143104-88-5) → Benzoic acid (R)-[(4R,5S,6R)-5-(tert-butyl-dimethyl-silanyloxy)-6-((E)-2-ethoxycarbonyl-vinyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethoxycarbonyl-methyl ester (178939-18-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / imidazole / dimethylformamide / 24 h

2: 83 percent / OsO₄, aq. N-methylmorpholine N-oxide / acetone / 4 h

3: 99 percent / pyridine, DMAP / 2 h / Ambient temperature

4: 68 percent / aq. HF / acetonitrile / 3 h / Ambient temperature

5: 90 percent / conc. H₂SO₄ / dimethylformamide / 24 h

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; sulfuric acid; hydrogen fluoride; 4-methylmorpholine N-oxide; In N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/0040-4020(96)00357-2

upstream raw materials:

2,2-dimethoxy-propane

(E)-(4R,5S,6R,7R)-7-Benzoyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dihydroxy-oct-2-enedioic acid diethyl ester

(4R,5R)-{5-[(E)-2''-ethoxycarbonyl-vinyl]-2',2'-dimethyl-[1',3']-dioxolan-4-yl}-(E)-acrylic acid ethyl ester

diethyl 4,5-dihydroxy-2,6-octadienedioate