1-((N-(benzyloxycarbonyl)-L-alanyl)oxy)-9-((methoxycarbonyl)dithio)phenoxathiin

Base Information

Chemical Name:1-((N-(benzyloxycarbonyl)-L-alanyl)oxy)-9-((methoxycarbonyl)dithio)phenoxathiin
CAS No.:120546-99-8
Molecular Formula:C₂₅H₂₁NO₇S₃
Molecular Weight:543.642
Hs Code.:

Synonyms:1-((N-(benzyloxycarbonyl)-L-alanyl)oxy)-9-((methoxycarbonyl)dithio)phenoxathiin

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Chemical Property of 1-((N-(benzyloxycarbonyl)-L-alanyl)oxy)-9-((methoxycarbonyl)dithio)phenoxathiin

Chemical Property:

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Technology Process of 1-((N-(benzyloxycarbonyl)-L-alanyl)oxy)-9-((methoxycarbonyl)dithio)phenoxathiin

There total 8 articles about 1-((N-(benzyloxycarbonyl)-L-alanyl)oxy)-9-((methoxycarbonyl)dithio)phenoxathiin 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: 89.0%

: 1142-20-7
N-Cbz-Ala

: 120577-46-0
1-hydroxy-9-((methoxycarbonyl)dithio)phenoxathiin

: 120546-99-8
1-((N-(benzyloxycarbonyl)-L-alanyl)oxy)-9-((methoxycarbonyl)dithio)phenoxathiin

Guidance literature:: With dicyclohexyl-carbodiimide; In dichloromethane; ethyl acetate; 1.) 0 deg C, 2 h, 2.) 25 deg C, 12 h;
DOI:10.1021/jo00276a027

Reference yield:

: 950-47-0
phenoxathiin S,S-dioxide

: 120546-99-8
1-((N-(benzyloxycarbonyl)-L-alanyl)oxy)-9-((methoxycarbonyl)dithio)phenoxathiin

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) n-BuLi, 2.) n-BuMgBr, O₂ / 1.) hexane, THF, -78 deg C, 1.5 h, 2.) Et₂O, -78 deg C to RT, 4.5 h

2: 92 percent / K₂CO₃ / acetone / 14 h / Heating

4: 30 percent / TiCl₄/THF, LiH / Heating

5: 48percent aq. HBr / acetic acid / 22 h / Heating

6: I₂ / methanol; CH₂Cl₂

7: 1.) Et₃P / 1.) dioxane, H₂O, 25 deg C, 10 min, 2.) MeOH, CH₂Cl₂, 5 min

8: 89 percent / dicyclohexylcarbodiimide / ethyl acetate; CH₂Cl₂ / 1.) 0 deg C, 2 h, 2.) 25 deg C, 12 h

With tetrahydrofuran; n-butyl magnesium bromide; n-butyllithium; hydrogen bromide; iodine; oxygen; titanium tetrachloride; lithium hydride; potassium carbonate; dicyclohexyl-carbodiimide; triethylphosphine; In methanol; dichloromethane; acetic acid; ethyl acetate; acetone;
DOI:10.1021/jo00276a027

Reference yield:

: 120546-90-9
1-hydroxyphenoxathiin 10,10-dioxide

: 120546-99-8
1-((N-(benzyloxycarbonyl)-L-alanyl)oxy)-9-((methoxycarbonyl)dithio)phenoxathiin

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / K₂CO₃ / acetone / 14 h / Heating

3: 30 percent / TiCl₄/THF, LiH / Heating

4: 48percent aq. HBr / acetic acid / 22 h / Heating

5: I₂ / methanol; CH₂Cl₂

6: 1.) Et₃P / 1.) dioxane, H₂O, 25 deg C, 10 min, 2.) MeOH, CH₂Cl₂, 5 min

7: 89 percent / dicyclohexylcarbodiimide / ethyl acetate; CH₂Cl₂ / 1.) 0 deg C, 2 h, 2.) 25 deg C, 12 h

With tetrahydrofuran; hydrogen bromide; iodine; titanium tetrachloride; lithium hydride; potassium carbonate; dicyclohexyl-carbodiimide; triethylphosphine; In methanol; dichloromethane; acetic acid; ethyl acetate; acetone;
DOI:10.1021/jo00276a027