(S)-2-(3-Phenyl-thioureido)-N-((3R,4R,4aR,5R,6R)-5,6,8-trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-yl)-propionamide

Base Information

• Chemical Name: (S)-2-(3-Phenyl-thioureido)-N-((3R,4R,4aR,5R,6R)-5,6,8-trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-yl)-propionamide
• CAS No.: 105866-04-4
• Molecular Formula: C₂₀H₂₅N₃O₆S
• Molecular Weight: 435.501
• Mol file: 105866-04-4.mol

Synonyms:

Chemical Property of (S)-2-(3-Phenyl-thioureido)-N-((3R,4R,4aR,5R,6R)-5,6,8-trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-yl)-propionamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-(3-Phenyl-thioureido)-N-((3R,4R,4aR,5R,6R)-5,6,8-trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-yl)-propionamide

There total 1 articles about (S)-2-(3-Phenyl-thioureido)-N-((3R,4R,4aR,5R,6R)-5,6,8-trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-yl)-propionamide 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: 90.0%

Actinobolin sulfate (18802-17-0,31327-55-6,33758-21-3) + phenyl isothiocyanate (103-72-0) → (S)-2-(3-Phenyl-thioureido)-N-((3R,4R,4aR,5R,6R)-5,6,8-trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-yl)-propionamide (105866-04-4)

Guidance literature:

With pyridine; for 3h; Ambient temperature;

DOI:10.1016/0040-4020(86)80003-5

Reference yield:

(S)-2-(3-Phenyl-thioureido)-N-((3R,4R,4aR,5R,6R)-5,6,8-trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-yl)-propionamide (105866-04-4) → ((3aR,8R,9R,9aR,9bR)-5-Methoxy-2,2,8-trimethyl-6-oxo-4,6,8,9,9a,9b-hexahydro-3aH-[1,3]dioxolo[4,5-f]isochromen-9-yl)-carbamic acid benzyl ester (105866-07-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / anhydrous hydrogen chloride / nitromethane / 0.5 h / Ambient temperature

2: 80 percent / triethylamine / ethyl acetate / 0 °C / stirring overnight at r.t.

3: 90 percent / pyridinium-p-toluenesulfonate / acetone / 18 h / Ambient temperature

4: 80 percent / methanol / 3 h / 0 °C

With hydrogenchloride; triethylamine; pyridinium p-toluenesulfonate; In methanol; nitromethane; ethyl acetate; acetone;

DOI:10.1016/0040-4020(86)80003-5

Reference yield:

(S)-2-(3-Phenyl-thioureido)-N-((3R,4R,4aR,5R,6R)-5,6,8-trihydroxy-3-methyl-1-oxo-3,4,4a,5,6,7-hexahydro-1H-isochromen-4-yl)-propionamide (105866-04-4) → ((3aR,8R,9R,9aR,9bR)-5-Hydroxy-2,2,8-trimethyl-6-oxo-4,6,8,9,9a,9b-hexahydro-3aH-[1,3]dioxolo[4,5-f]isochromen-9-yl)-carbamic acid benzyl ester (105928-74-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / anhydrous hydrogen chloride / nitromethane / 0.5 h / Ambient temperature

2: 80 percent / triethylamine / ethyl acetate / 0 °C / stirring overnight at r.t.

3: 90 percent / pyridinium-p-toluenesulfonate / acetone / 18 h / Ambient temperature

With hydrogenchloride; triethylamine; pyridinium p-toluenesulfonate; In nitromethane; ethyl acetate; acetone;

DOI:10.1016/0040-4020(86)80003-5

upstream raw materials:

Actinobolin sulfate

phenyl isothiocyanate

Downstream raw materials:

N-Carbobenzyloxydesalanylactinobolin

((3aR,8R,9R,9aR,9bR)-5-Hydroxy-2,2,8-trimethyl-6-oxo-4,6,8,9,9a,9b-hexahydro-3aH-[1,3]dioxolo[4,5-f]isochromen-9-yl)-carbamic acid benzyl ester

((3aR,8R,9R,9aR,9bR)-5-Methoxy-2,2,8-trimethyl-6-oxo-4,6,8,9,9a,9b-hexahydro-3aH-[1,3]dioxolo[4,5-f]isochromen-9-yl)-carbamic acid benzyl ester