(7aR,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chro men-7(7aH)-one O-benzyloxime

Base Information

Chemical Name:(7aR,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chro men-7(7aH)-one O-benzyloxime
CAS No.:1386350-15-7
Molecular Formula:C₃₀H₂₉NO₆
Molecular Weight:499.563
Hs Code.:

Synonyms:(7aR,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chro men-7(7aH)-one O-benzyloxime

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Chemical Property of (7aR,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chro men-7(7aH)-one O-benzyloxime

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Technology Process of (7aR,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chro men-7(7aH)-one O-benzyloxime

There total 6 articles about (7aR,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chro men-7(7aH)-one O-benzyloxime 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: 33.0%

: 112797-42-9
(7aR,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one oxime

: 100-39-0
benzyl bromide

: 1386350-15-7
(7aR,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chro men-7(7aH)-one O-benzyloxime

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; at 0 ℃;
DOI:10.1021/jm301488q

Reference yield:

: 83-79-4
rotenone

: 1386350-15-7
(7aR,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chro men-7(7aH)-one O-benzyloxime

Guidance literature:: Multi-step reaction with 5 steps

1.1: boron tribromide / dichloromethane / 0.08 h / -10 °C

2.1: N,N,N,N,N,N-hexamethylphosphoric triamide; sodium cyanoborohydride / 3 h / 70 °C

3.1: Phenylselenyl chloride / dichloromethane / 1.17 h / -30 - 20 °C

3.2: 0 °C

4.1: pyridine; hydroxylamine hydrochloride / 70 °C

5.1: potassium tert-butylate / tetrahydrofuran / 0 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; Phenylselenyl chloride; hydroxylamine hydrochloride; potassium tert-butylate; boron tribromide; sodium cyanoborohydride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jm301488q

Reference yield:

: 70191-70-7
4'-bromorot-2'-enonic acid

: 1386350-15-7
(7aR,13aS)-9,10-dimethoxy-3,3-dimethyl-13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chro men-7(7aH)-one O-benzyloxime

Guidance literature:: Multi-step reaction with 4 steps

1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; sodium cyanoborohydride / 3 h / 70 °C

2.1: Phenylselenyl chloride / dichloromethane / 1.17 h / -30 - 20 °C

2.2: 0 °C

3.1: pyridine; hydroxylamine hydrochloride / 70 °C

4.1: potassium tert-butylate / tetrahydrofuran / 0 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; Phenylselenyl chloride; hydroxylamine hydrochloride; potassium tert-butylate; sodium cyanoborohydride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jm301488q