(5aR,9aS)-4-Acetyl-8-methoxy-2,7-dimethyl-5,10-dioxo-9-phenylsulfanyl-3,4,5,5a,6,9,9a,10-octahydro-2H-naphtho[2,3-b][1,4]oxazine-2-carboxylic acid methyl ester

Base Information

Chemical Name:(5aR,9aS)-4-Acetyl-8-methoxy-2,7-dimethyl-5,10-dioxo-9-phenylsulfanyl-3,4,5,5a,6,9,9a,10-octahydro-2H-naphtho[2,3-b][1,4]oxazine-2-carboxylic acid methyl ester
CAS No.:77270-69-0
Molecular Formula:C₂₅H₂₇NO₇S
Molecular Weight:485.558
Hs Code.:

(5aR,9aS)-4-Acetyl-8-methoxy-2,7-dimethyl-5,10-dioxo-9-phenylsulfanyl-3,4,5,5a,6,9,9a,10-octahydro-2H-naphtho[2,3-b][1,4]oxazine-2-carboxylic acid methyl ester

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Chemical Property of (5aR,9aS)-4-Acetyl-8-methoxy-2,7-dimethyl-5,10-dioxo-9-phenylsulfanyl-3,4,5,5a,6,9,9a,10-octahydro-2H-naphtho[2,3-b][1,4]oxazine-2-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (5aR,9aS)-4-Acetyl-8-methoxy-2,7-dimethyl-5,10-dioxo-9-phenylsulfanyl-3,4,5,5a,6,9,9a,10-octahydro-2H-naphtho[2,3-b][1,4]oxazine-2-carboxylic acid methyl ester

There total 11 articles about (5aR,9aS)-4-Acetyl-8-methoxy-2,7-dimethyl-5,10-dioxo-9-phenylsulfanyl-3,4,5,5a,6,9,9a,10-octahydro-2H-naphtho[2,3-b][1,4]oxazine-2-carboxylic acid methyl 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:

: 77270-59-8
2-Amino-3-(2-methoxy-ethoxymethoxy)-phenol

: 77270-69-0
(5aR,9aS)-4-Acetyl-8-methoxy-2,7-dimethyl-5,10-dioxo-9-phenylsulfanyl-3,4,5,5a,6,9,9a,10-octahydro-2H-naphtho[2,3-b][1,4]oxazine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 98 percent / K₂CO₃ / acetone / 12 h / Heating

2: 96 percent / NaI, K₂CO₃ / acetone / 15 h / 90 °C

3: 100 percent / 5percent KOH / ethanol; tetrahydrofuran / 1 h / Ambient temperature

4: 1.) (i-Pr)2NLi / 1.) THF, -50 deg C, 2 h, 2.) from -50 deg C to room temp.

5: methanol

6: 100 percent / H₂, HCl / 10percent Pd/C / benzene; ethanol / 6 h / Ambient temperature

7: 94 percent / pyridine / 5 h / 110 °C

8: 99 percent / HCl(gas) / methanol / 0.17 h / 40 °C

9: 84 percent / Fremy's salt, 1/6 M KH₂PO₄ / 2 h / Ambient temperature

10: ZnCl₂ / CH₂Cl₂ / 6 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; potassium dihydrogenphosphate; potassiuim nitrosodisulfonate; hydrogen; potassium carbonate; sodium iodide; zinc(II) chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; acetone; benzene;
DOI:10.1021/jo00324a054

Reference yield:

: 77270-58-7
3-(2-Methoxy-ethoxymethoxy)-2-nitro-phenol

: 77270-69-0
(5aR,9aS)-4-Acetyl-8-methoxy-2,7-dimethyl-5,10-dioxo-9-phenylsulfanyl-3,4,5,5a,6,9,9a,10-octahydro-2H-naphtho[2,3-b][1,4]oxazine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 100 percent / H₂, NaBH₄, 2 N NaOH / 10percent Pd/C / 0.5 h / Ambient temperature

2: 98 percent / K₂CO₃ / acetone / 12 h / Heating

3: 96 percent / NaI, K₂CO₃ / acetone / 15 h / 90 °C

4: 100 percent / 5percent KOH / ethanol; tetrahydrofuran / 1 h / Ambient temperature

5: 1.) (i-Pr)2NLi / 1.) THF, -50 deg C, 2 h, 2.) from -50 deg C to room temp.

6: methanol

7: 100 percent / H₂, HCl / 10percent Pd/C / benzene; ethanol / 6 h / Ambient temperature

8: 94 percent / pyridine / 5 h / 110 °C

9: 99 percent / HCl(gas) / methanol / 0.17 h / 40 °C

10: 84 percent / Fremy's salt, 1/6 M KH₂PO₄ / 2 h / Ambient temperature

11: ZnCl₂ / CH₂Cl₂ / 6 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; potassium dihydrogenphosphate; potassiuim nitrosodisulfonate; hydrogen; potassium carbonate; sodium iodide; zinc(II) chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; acetone; benzene;
DOI:10.1021/jo00324a054

Reference yield:

: 77270-60-1
5-(2-Methoxy-ethoxymethoxy)-3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid methyl ester

: 77270-69-0
(5aR,9aS)-4-Acetyl-8-methoxy-2,7-dimethyl-5,10-dioxo-9-phenylsulfanyl-3,4,5,5a,6,9,9a,10-octahydro-2H-naphtho[2,3-b][1,4]oxazine-2-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 96 percent / NaI, K₂CO₃ / acetone / 15 h / 90 °C

2: 100 percent / 5percent KOH / ethanol; tetrahydrofuran / 1 h / Ambient temperature

3: 1.) (i-Pr)2NLi / 1.) THF, -50 deg C, 2 h, 2.) from -50 deg C to room temp.

4: methanol

5: 100 percent / H₂, HCl / 10percent Pd/C / benzene; ethanol / 6 h / Ambient temperature

6: 94 percent / pyridine / 5 h / 110 °C

7: 99 percent / HCl(gas) / methanol / 0.17 h / 40 °C

8: 84 percent / Fremy's salt, 1/6 M KH₂PO₄ / 2 h / Ambient temperature

9: ZnCl₂ / CH₂Cl₂ / 6 h / Ambient temperature

With hydrogenchloride; potassium hydroxide; potassium dihydrogenphosphate; potassiuim nitrosodisulfonate; hydrogen; potassium carbonate; sodium iodide; zinc(II) chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; acetone; benzene;
DOI:10.1021/jo00324a054