Acetic acid (3S,4R,4aR,6S,6aS,12aR,12bS)-3-acetoxy-4-acetoxymethyl-4,6a,12b-trimethyl-11,12-dioxo-9-phenyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-6-yl ester

Base Information

Chemical Name:Acetic acid (3S,4R,4aR,6S,6aS,12aR,12bS)-3-acetoxy-4-acetoxymethyl-4,6a,12b-trimethyl-11,12-dioxo-9-phenyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-6-yl ester
CAS No.:189564-14-5
Molecular Formula:C₃₂H₃₆O₁₀
Molecular Weight:580.632
Hs Code.:

Acetic acid (3S,4R,4aR,6S,6aS,12aR,12bS)-3-acetoxy-4-acetoxymethyl-4,6a,12b-trimethyl-11,12-dioxo-9-phenyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-6-yl ester

Synonyms:Acetic acid (3S,4R,4aR,6S,6aS,12aR,12bS)-3-acetoxy-4-acetoxymethyl-4,6a,12b-trimethyl-11,12-dioxo-9-phenyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-6-yl ester

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Chemical Property of Acetic acid (3S,4R,4aR,6S,6aS,12aR,12bS)-3-acetoxy-4-acetoxymethyl-4,6a,12b-trimethyl-11,12-dioxo-9-phenyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-6-yl ester

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Technology Process of Acetic acid (3S,4R,4aR,6S,6aS,12aR,12bS)-3-acetoxy-4-acetoxymethyl-4,6a,12b-trimethyl-11,12-dioxo-9-phenyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-6-yl ester

There total 10 articles about Acetic acid (3S,4R,4aR,6S,6aS,12aR,12bS)-3-acetoxy-4-acetoxymethyl-4,6a,12b-trimethyl-11,12-dioxo-9-phenyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-6-yl 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: 89.0%

: 108-24-7
acetic anhydride

: 189564-10-1
(3S,4R,4aR,6S,6aS,12aR,12bS)-3,6-Dihydroxy-4-hydroxymethyl-4,6a,12b-trimethyl-9-phenyl-1,2,3,4,4a,5,6,6a,12a,12b-decahydro-7,10-dioxa-benzo[a]anthracene-11,12-dione

: 189564-14-5
Acetic acid (3S,4R,4aR,6S,6aS,12aR,12bS)-3-acetoxy-4-acetoxymethyl-4,6a,12b-trimethyl-11,12-dioxo-9-phenyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-6-yl ester

Guidance literature:: With dmap; In pyridine; at 25 ℃; for 72h; evapn., purification by PTLC;
DOI:10.7164/antibiotics.50.229

Reference yield:

: 189564-01-0
(4aS,5S,6aR,7R,8S,10aS,10bR)-3,4a,7,10a-Tetramethyl-1-oxo-5,8-bis-trimethylsilanyloxy-7-trimethylsilanyloxymethyl-4a,5,6,6a,7,8,9,10,10a,10b-decahydro-1H-benzo[f]chromene-2-carboxylic acid methyl ester

: 189564-14-5
Acetic acid (3S,4R,4aR,6S,6aS,12aR,12bS)-3-acetoxy-4-acetoxymethyl-4,6a,12b-trimethyl-11,12-dioxo-9-phenyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-6-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / lithium bis(trimethylsilyl)amide; N,N,N',N'-tetramethylethylenediamine / tetrahydrofuran / 4 h / 0 - 25 °C / under Ar; Li reagent and TMEDA mixing, starting compound, then chloroanhidride adding; quenching with AcOH

2: 77 percent / HCl / methanol; H₂O / 1 h / 25 °C / 2 N HCl; purification by reverse phase TLC

3: 89 percent / 4-dimethylaminopyridine / pyridine / 72 h / 25 °C / evapn., purification by PTLC

With hydrogenchloride; dmap; N,N,N,N,-tetramethylethylenediamine; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; methanol; water; 1: Cyclization / 2: Hydrolysis / 3: Substitution;
DOI:10.7164/antibiotics.50.229

Reference yield:

: 98-88-4
benzoyl chloride

: 189564-14-5
Acetic acid (3S,4R,4aR,6S,6aS,12aR,12bS)-3-acetoxy-4-acetoxymethyl-4,6a,12b-trimethyl-11,12-dioxo-9-phenyl-1,3,4,4a,5,6,6a,12,12a,12b-decahydro-2H,11H-7,10-dioxa-benzo[a]anthracen-6-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 80 percent / lithium bis(trimethylsilyl)amide; N,N,N',N'-tetramethylethylenediamine / tetrahydrofuran / 4 h / 0 - 25 °C / under Ar; Li reagent and TMEDA mixing, starting compound, then chloroanhidride adding; quenching with AcOH

2: 77 percent / HCl / methanol; H₂O / 1 h / 25 °C / 2 N HCl; purification by reverse phase TLC

3: 89 percent / 4-dimethylaminopyridine / pyridine / 72 h / 25 °C / evapn., purification by PTLC

With hydrogenchloride; dmap; N,N,N,N,-tetramethylethylenediamine; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; methanol; water; 1: Cyclization / 2: Hydrolysis / 3: Substitution;
DOI:10.7164/antibiotics.50.229