(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

Base Information

• Chemical Name: (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
• CAS No.: 189564-10-1
• Molecular Formula: C₂₆H₃₀O₇
• Molecular Weight: 454.52
• Mol file: 189564-10-1.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 10 articles about (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 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: 77.0%

(1R,4aS,5S,6aR,7R,8S,10aS,10bS)-1-Hydroxy-3-((Z)-2-hydroxy-2-phenyl-vinyl)-4a,7,10a-trimethyl-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 → (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 (189564-10-1)

Guidance literature:

With hydrogenchloride; In methanol; water; at 25 ℃; for 1h; 2 N HCl; purification by reverse phase TLC;

DOI:10.7164/antibiotics.50.229

Reference yield:

(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 (189564-01-0) → (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 (189564-10-1)

Guidance literature:

Multi-step reaction with 2 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

With hydrogenchloride; N,N,N,N,-tetramethylethylenediamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; water; 1: Cyclization / 2: Hydrolysis;

DOI:10.7164/antibiotics.50.229

Reference yield:

benzoyl chloride (98-88-4) → (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 (189564-10-1)

Guidance literature:

Multi-step reaction with 2 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

With hydrogenchloride; N,N,N,N,-tetramethylethylenediamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; water; 1: Cyclization / 2: Hydrolysis;

DOI:10.7164/antibiotics.50.229

upstream raw materials:

(3S,4R,4aR,6S,6aS,12aR,12bS)-4,6a,12b-Trimethyl-9-phenyl-3,6-bis-trimethylsilanyloxy-4-trimethylsilanyloxymethyl-1,2,3,4,4a,5,6,6a,12a,12b-decahydro-7,10-dioxa-benzo[a]anthracene-11,12-dione

benzoyl chloride

(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

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

Downstream raw materials:

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