benzyl-7-((3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxotetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-8-methyl-2-oxo-2H-chromen-3-yl carbamate

Base Information

• Chemical Name: benzyl-7-((3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxotetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-8-methyl-2-oxo-2H-chromen-3-yl carbamate
• CAS No.: 915118-11-5
• Molecular Formula: C₂₇H₂₇NO₁₀
• Molecular Weight: 525.512
• Mol file: 915118-11-5.mol

Synonyms:benzyl-7-((3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxotetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-8-methyl-2-oxo-2H-chromen-3-yl carbamate

Chemical Property of benzyl-7-((3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxotetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-8-methyl-2-oxo-2H-chromen-3-yl carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl-7-((3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxotetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-8-methyl-2-oxo-2H-chromen-3-yl carbamate

There total 4 articles about benzyl-7-((3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxotetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-8-methyl-2-oxo-2H-chromen-3-yl carbamate 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%

3-(benzyloxycarbonyl)amino-7-hydroxy-8-methyl-2H-1-benzopyran-2-one (223718-30-7) + (3aR,4S,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxo-tetrahydro-3aH-[1,3]-dioxolo[4,5-c]pyran-4-yl 2,2,2-trichloroacetimidate (301187-46-2) → benzyl-7-((3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxotetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-8-methyl-2-oxo-2H-chromen-3-yl carbamate (915118-11-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 14h;

DOI:10.1021/ol061918j DOI:10.1021/ja065793p

Reference yield: 81.0%

(3aR,4S,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxo-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl 2,2,2-trichloroacetamidate (1083312-89-3) + 3-(benzyloxycarbonyl)amino-7-hydroxy-8-methyl-2H-1-benzopyran-2-one (223718-30-7) → benzyl-7-((3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxotetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-8-methyl-2-oxo-2H-chromen-3-yl carbamate (915118-11-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 14h;

DOI:10.1021/jo702191a

Reference yield:

2-methylbenzene-1,3-diol (608-25-3) → benzyl-7-((3aR,4R,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxotetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-8-methyl-2-oxo-2H-chromen-3-yl carbamate (915118-11-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 41 percent / acetic acid / 48 h / Heating

2: 81 percent / boron trifluoride etherate / CH₂Cl₂ / 14 h

With boron trifluoride diethyl etherate; In dichloromethane; acetic acid;

DOI:10.1021/ja065793p

upstream raw materials:

3-(benzyloxycarbonyl)amino-7-hydroxy-8-methyl-2H-1-benzopyran-2-one

(3aR,4S,7R,7aR)-7-methoxy-6,6-dimethyl-2-oxo-tetrahydro-3aH-[1,3]-dioxolo[4,5-c]pyran-4-yl 2,2,2-trichloroacetimidate

2-methylbenzene-1,3-diol

Methyl (Z)-2-<(benzyloxycarbonyl)amino>-3-dimethylaminopropenoate

Downstream raw materials:

benzyl 7-((2R,3R,4S,5R)-3,4-dihydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2-yloxy)-8-methyl-2-oxo-2H-chromen-3-ylcarbamate