(1S,2S,3R,4R,5R,6S)-4-(7-methoxybenzo[d][1,3]dioxol-5-yl)-5-(methoxycarbonyl)amino-6-(methoxycarbonyloxy)cyclohexane-1,2,3-triyl triacetate

Base Information

• Chemical Name: (1S,2S,3R,4R,5R,6S)-4-(7-methoxybenzo[d][1,3]dioxol-5-yl)-5-(methoxycarbonyl)amino-6-(methoxycarbonyloxy)cyclohexane-1,2,3-triyl triacetate
• CAS No.: 1415407-80-5
• Molecular Formula: C₂₄H₂₉NO₁₄
• Molecular Weight: 555.493
• Mol file: 1415407-80-5.mol

Synonyms:

Chemical Property of (1S,2S,3R,4R,5R,6S)-4-(7-methoxybenzo[d][1,3]dioxol-5-yl)-5-(methoxycarbonyl)amino-6-(methoxycarbonyloxy)cyclohexane-1,2,3-triyl triacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,3R,4R,5R,6S)-4-(7-methoxybenzo[d][1,3]dioxol-5-yl)-5-(methoxycarbonyl)amino-6-(methoxycarbonyloxy)cyclohexane-1,2,3-triyl triacetate

There total 4 articles about (1S,2S,3R,4R,5R,6S)-4-(7-methoxybenzo[d][1,3]dioxol-5-yl)-5-(methoxycarbonyl)amino-6-(methoxycarbonyloxy)cyclohexane-1,2,3-triyl triacetate 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:

C18H23NO11 + acetic anhydride (108-24-7) → (1S,2S,3R,4R,5R,6S)-4-(7-methoxybenzo[d][1,3]dioxol-5-yl)-5-(methoxycarbonyl)amino-6-(methoxycarbonyloxy)cyclohexane-1,2,3-triyl triacetate (1415407-80-5)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/jo3022567

Reference yield:

C17H21NO7 → (1S,2S,3R,4R,5R,6S)-4-(7-methoxybenzo[d][1,3]dioxol-5-yl)-5-(methoxycarbonyl)amino-6-(methoxycarbonyloxy)cyclohexane-1,2,3-triyl triacetate (1415407-80-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dmap / dichloromethane / 2 h / 20 °C

2.1: Dowex 50WX / methanol / 48 h / 60 °C

2.2: 2 h / 20 °C / Inert atmosphere

3.1: dmap; triethylamine / dichloromethane / 4 h / 20 °C

With dmap; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jo3022567

Reference yield:

(1R,5S,6S,7R,8R)-8-(7-methoxy-1,3-benzodioxol-5-yl)-7-[(methoxycarbonyl)amino]-3,3-dimethyl-9-oxo-2,4-dioxabicyclo[3.3.1]non-6-yl methyl carbonate → (1S,2S,3R,4R,5R,6S)-4-(7-methoxybenzo[d][1,3]dioxol-5-yl)-5-(methoxycarbonyl)amino-6-(methoxycarbonyloxy)cyclohexane-1,2,3-triyl triacetate (1415407-80-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Dowex 50WX / methanol / 48 h / 60 °C

1.2: 2 h / 20 °C / Inert atmosphere

2.1: dmap; triethylamine / dichloromethane / 4 h / 20 °C

With dmap; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jo3022567

upstream raw materials:

C₁₇H₁₉NO₉

acetic anhydride

Downstream raw materials:

pancratistatin