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

Base Information

• Chemical Name: (E)-(4R,5S,6R,7R)-7-Benzoyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dihydroxy-oct-2-enedioic acid diethyl ester
• CAS No.: 178939-04-3
• Molecular Formula: C₂₅H₃₈O₉Si
• Molecular Weight: 510.657
• Mol file: 178939-04-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (E)-(4R,5S,6R,7R)-7-Benzoyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dihydroxy-oct-2-enedioic acid diethyl 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: 68.0%

(E)-(4R,5R,6R,7R)-7-Benzoyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-oct-2-enedioic acid diethyl ester (178939-03-2) → (E)-(4R,5S,6R,7R)-7-Benzoyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dihydroxy-oct-2-enedioic acid diethyl ester (178939-04-3)

Guidance literature:

With hydrogen fluoride; In acetonitrile; for 3h; Ambient temperature;

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) → (E)-(4R,5S,6R,7R)-7-Benzoyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dihydroxy-oct-2-enedioic acid diethyl ester (178939-04-3)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; 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) → (E)-(4R,5S,6R,7R)-7-Benzoyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dihydroxy-oct-2-enedioic acid diethyl ester (178939-04-3)

Guidance literature:

Multi-step reaction with 4 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

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

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

upstream raw materials:

(E)-(4R,5R,6R,7R)-7-Benzoyloxy-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-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

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

Downstream raw materials:

(E)-(4R,5R,6R,7R)-4,7-Bis-benzoyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-oct-2-enedioic acid diethyl ester

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

diethyl (4R,5S,6S,7R)-4-azido-7-benzoyloxy-5-(tert-butyldimethylsilanyloxy)-6-hydroxy-oct-2-enedioate

(3R,4S,5S,6S)-3-benzoyloxy-5-(tert-butyldimethylsilanyloxy)-6-(2-ethoxycarbonylvinyl)-4-hydroxy-piperidin-2-one