(3S,5S,7S,9R,11R,13R)-9,11,15-Trihydroxy-5,7-(isopropylidenedioxy)-3,13-di[(4-methoxybenzoyl)oxy]pentadec-1-yl pivalate

Base Information

Chemical Name:(3S,5S,7S,9R,11R,13R)-9,11,15-Trihydroxy-5,7-(isopropylidenedioxy)-3,13-di[(4-methoxybenzoyl)oxy]pentadec-1-yl pivalate
CAS No.:321146-53-6
Molecular Formula:C₃₉H₅₆O₁₃
Molecular Weight:732.866
Hs Code.:

Synonyms:(3S,5S,7S,9R,11R,13R)-9,11,15-Trihydroxy-5,7-(isopropylidenedioxy)-3,13-di[(4-methoxybenzoyl)oxy]pentadec-1-yl pivalate

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Chemical Property of (3S,5S,7S,9R,11R,13R)-9,11,15-Trihydroxy-5,7-(isopropylidenedioxy)-3,13-di[(4-methoxybenzoyl)oxy]pentadec-1-yl pivalate

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Technology Process of (3S,5S,7S,9R,11R,13R)-9,11,15-Trihydroxy-5,7-(isopropylidenedioxy)-3,13-di[(4-methoxybenzoyl)oxy]pentadec-1-yl pivalate

There total 5 articles about (3S,5S,7S,9R,11R,13R)-9,11,15-Trihydroxy-5,7-(isopropylidenedioxy)-3,13-di[(4-methoxybenzoyl)oxy]pentadec-1-yl pivalate 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: 67.0%

: 321146-51-4
(1R,6R)-6-Hydroxy-4-{(2S,4S,6S)-8-[(2,2-dimethylpropanoyl)oxy]-2,4-isopropylidenedioxy-6-[(4-methoxybenzoyl)oxy]octyl}cyclohept-3-en-1-yl 4-methoxybenzoate

: 321146-53-6
(3S,5S,7S,9R,11R,13R)-9,11,15-Trihydroxy-5,7-(isopropylidenedioxy)-3,13-di[(4-methoxybenzoyl)oxy]pentadec-1-yl pivalate

Guidance literature:: (1R,6R)-6-Hydroxy-4-{(2S,4S,6S)-8-[(2,2-dimethylpropanoyl)oxy]-2,4-isopropylidenedioxy-6-[(4-methoxybenzoyl)oxy]octyl}cyclohept-3-en-1-yl 4-methoxybenzoate; With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In tetrachloromethane; acetone;

With lead(IV) acetate; acetic acid; In benzene; at 20 ℃; for 0.5h;

With tetramethylammonium triacetoxyborohydride; In acetic acid; acetonitrile; at 2 ℃; for 168h; Further stages.;
DOI:10.1002/1521-3765(20001117)6:22<4091::AID-CHEM4091>3.0.CO;2-W

Reference yield:

: 3282-30-2
pivaloyl chloride

: 321146-53-6
(3S,5S,7S,9R,11R,13R)-9,11,15-Trihydroxy-5,7-(isopropylidenedioxy)-3,13-di[(4-methoxybenzoyl)oxy]pentadec-1-yl pivalate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 70 percent / pyridine / CH₂Cl₂ / 3 h / 0 °C

2.1: N-methylmorpholine N-oxide; OsO₄; H₂O / acetone; CCl₄

2.2: Pb(OAc)4; AcOH / benzene / 0.5 h / 20 °C

2.3: 67 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / 168 h / 2 °C

With pyridine; osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In tetrachloromethane; dichloromethane; acetone;
DOI:10.1002/1521-3765(20001117)6:22<4091::AID-CHEM4091>3.0.CO;2-W

Reference yield:

: (2RS,4S,6R)-Tetrahydro-2-hydroxy-6-{(4S,6S)-{6-hydroxy-4-[(4-methoxybenzoyl)oxy]cyclohept-1-en-1-yl}-2-oxopropyl}-2H-pyrann-4-yl 4-methoxybenzoate

: 321146-53-6
(3S,5S,7S,9R,11R,13R)-9,11,15-Trihydroxy-5,7-(isopropylidenedioxy)-3,13-di[(4-methoxybenzoyl)oxy]pentadec-1-yl pivalate

Guidance literature:: Multi-step reaction with 4 steps

1.1: Et₂BOMe / tetrahydrofuran / 1 h / -78 - 20 °C

1.2: 57 percent / NaBH₄; B(OH)3 / methanol; tetrahydrofuran / 5 h / -10 °C

2.1: 78 percent / pyridine para-toluenesulfonate / acetone / 2 h / 20 °C

3.1: 70 percent / pyridine / CH₂Cl₂ / 3 h / 0 °C

4.1: N-methylmorpholine N-oxide; OsO₄; H₂O / acetone; CCl₄

4.2: Pb(OAc)4; AcOH / benzene / 0.5 h / 20 °C

4.3: 67 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / 168 h / 2 °C

With pyridine; osmium(VIII) oxide; diethyl methoxy borane; water; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; In tetrahydrofuran; tetrachloromethane; dichloromethane; acetone;
DOI:10.1002/1521-3765(20001117)6:22<4091::AID-CHEM4091>3.0.CO;2-W