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

Base Information

Chemical Name:(E)-(4S,5R,6R,7R)-4,7-Bis-benzoyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-oct-2-enedioic acid diethyl ester
CAS No.:178939-06-5
Molecular Formula:C₃₂H₄₂O₁₀Si
Molecular Weight:614.765
Hs Code.:

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

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

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

There total 6 articles about (E)-(4S,5R,6R,7R)-4,7-Bis-benzoyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-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: 90.0%

: 65-85-0,8013-63-6
benzoic acid

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

: 178939-06-5
(E)-(4S,5R,6R,7R)-4,7-Bis-benzoyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-oct-2-enedioic acid diethyl ester

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 4h; Ambient temperature;
DOI:10.1016/0040-4020(96)00357-2

Reference yield:

: 114473-50-6
(4R,5R)-{5-[(E)-2''-ethoxycarbonyl-vinyl]-2',2'-dimethyl-[1',3']-dioxolan-4-yl}-(E)-acrylic acid ethyl ester

: 178939-06-5
(E)-(4S,5R,6R,7R)-4,7-Bis-benzoyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-oct-2-enedioic acid diethyl ester

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 / PPh₃, DEAD / tetrahydrofuran / 4 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; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1016/0040-4020(96)00357-2

Reference yield:

: 143104-88-5
diethyl 4,5-dihydroxy-2,6-octadienedioate

: 178939-06-5
(E)-(4S,5R,6R,7R)-4,7-Bis-benzoyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-oct-2-enedioic acid diethyl ester

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 / PPh₃, DEAD / tetrahydrofuran / 4 h / Ambient temperature

With pyridine; 1H-imidazole; dmap; osmium(VIII) oxide; hydrogen fluoride; 4-methylmorpholine N-oxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; N,N-dimethyl-formamide; acetone; acetonitrile;
DOI:10.1016/0040-4020(96)00357-2