(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3,12-dihydroxy-4-(hydroxymethyl)-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,2,3,4,4a,5,6,6a,11,12,12a,12b-dodecahydrobenzo[f]pyrano[4,3-b]chromen-6-yl 4-cyanobenzoate

Base Information

• Chemical Name: (3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3,12-dihydroxy-4-(hydroxymethyl)-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,2,3,4,4a,5,6,6a,11,12,12a,12b-dodecahydrobenzo[f]pyrano[4,3-b]chromen-6-yl 4-cyanobenzoate
• CAS No.: 1163689-90-4
• Molecular Formula: C₃₃H₃₄N₂O₈
• Molecular Weight: 586.642

Synonyms:(3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3,12-dihydroxy-4-(hydroxymethyl)-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,2,3,4,4a,5,6,6a,11,12,12a,12b-dodecahydrobenzo[f]pyrano[4,3-b]chromen-6-yl 4-cyanobenzoate

Chemical Property of (3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3,12-dihydroxy-4-(hydroxymethyl)-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,2,3,4,4a,5,6,6a,11,12,12a,12b-dodecahydrobenzo[f]pyrano[4,3-b]chromen-6-yl 4-cyanobenzoate

Chemical Property:

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Technology Process of (3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3,12-dihydroxy-4-(hydroxymethyl)-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,2,3,4,4a,5,6,6a,11,12,12a,12b-dodecahydrobenzo[f]pyrano[4,3-b]chromen-6-yl 4-cyanobenzoate

There total 6 articles about (3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3,12-dihydroxy-4-(hydroxymethyl)-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,2,3,4,4a,5,6,6a,11,12,12a,12b-dodecahydrobenzo[f]pyrano[4,3-b]chromen-6-yl 4-cyanobenzoate 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: 81.0%

7-O-p-cyanobenzoyl-1,11-O-(di-tert-butylsilylene)-1,7,11-trideacetylpyripyropene A (1163689-88-0) → (3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-((di-tert-butylfluorosilyl)oxy)-12-hydroxy-4-(hydroxymethyl)-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,2,3,4,4a,5,6,6a,11,12,12a,12b-dodecahydrobenzo[f]pyrano[4,3-b]chromen-6-yl 4-cyanobenzoate (1259032-84-2) + (3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3,12-dihydroxy-4-(hydroxymethyl)-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,2,3,4,4a,5,6,6a,11,12,12a,12b-dodecahydrobenzo[f]pyrano[4,3-b]chromen-6-yl 4-cyanobenzoate (1163689-90-4) + (3S,4R,4aR,6S,6aS,12R,12aS,12bS)-4-(((di-tert-butylfluorosilyl)oxy)methyl)-3,12-dihydroxy-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,2,3,4,4a,5,6,6a,11,12,12a,12bdodecahydrobenzo[f]pyrano[4,3-b]chromen-6-yl 4-cyanobenzoate (1259032-85-3)

Guidance literature:

With ammonium fluoride; In methanol; at 20 ℃; for 3h; regioselective reaction;

DOI:10.1246/bcsj.20130237

Reference yield:

α-pyronemeroterpenoid pyripyropene A (147444-03-9) → (3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-((di-tert-butylfluorosilyl)oxy)-12-hydroxy-4-(hydroxymethyl)-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,2,3,4,4a,5,6,6a,11,12,12a,12b-dodecahydrobenzo[f]pyrano[4,3-b]chromen-6-yl 4-cyanobenzoate (1259032-84-2) + (3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3,12-dihydroxy-4-(hydroxymethyl)-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,2,3,4,4a,5,6,6a,11,12,12a,12b-dodecahydrobenzo[f]pyrano[4,3-b]chromen-6-yl 4-cyanobenzoate (1163689-90-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium methylate / methanol / 20 °C

1.2: 0 °C

1.3: 20 °C

2.1: ammonium fluoride / tetrahydrofuran / 24 h / 20 °C

With ammonium fluoride; sodium methylate; In tetrahydrofuran; methanol;

DOI:10.1246/bcsj.20130237

Reference yield:

4-cyanobenzoic Acid (619-65-8,333406-09-0) → (3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3-((di-tert-butylfluorosilyl)oxy)-12-hydroxy-4-(hydroxymethyl)-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,2,3,4,4a,5,6,6a,11,12,12a,12b-dodecahydrobenzo[f]pyrano[4,3-b]chromen-6-yl 4-cyanobenzoate (1259032-84-2) + (3S,4R,4aR,6S,6aS,12R,12aS,12bS)-3,12-dihydroxy-4-(hydroxymethyl)-4,6a,12b-trimethyl-11-oxo-9-(pyridin-3-yl)-1,2,3,4,4a,5,6,6a,11,12,12a,12b-dodecahydrobenzo[f]pyrano[4,3-b]chromen-6-yl 4-cyanobenzoate (1163689-90-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium methylate / methanol / 20 °C

1.2: 0 °C

1.3: 20 °C

2.1: ammonium fluoride / tetrahydrofuran / 24 h / 20 °C

With ammonium fluoride; sodium methylate; In tetrahydrofuran; methanol;

DOI:10.1246/bcsj.20130237

upstream raw materials:

α-pyronemeroterpenoid pyripyropene A

7-O-p-cyanobenzoyl-1,11-O-(di-tert-butylsilylene)-1,7,11-trideacetylpyripyropene A

4-cyanobenzoic Acid

Downstream raw materials:

7-O-p-cyanobenzoyl-1,11-O-dibenzoyl-1,7,11-trideacetyl-pyripyropene A

7-O-p-cyanobenzoyl-1,11-O-dihexanoyl-1,7,11-trideacetyl-pyripyropene A

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