(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
Hs Code.:

(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

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

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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

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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

: 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

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:

: 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

: 189564-10-1
(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

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:

: 98-88-4
benzoyl chloride

: 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

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