methyl <1'R,2'S,5'R,6'S>-2-<1'-formyl-1'-hydroperoxy-5'-methyl-6'-(3''-oxobutyl)cyclohex-2'-yl>propenoate

Base Information

• Chemical Name: methyl <1'R,2'S,5'R,6'S>-2-<1'-formyl-1'-hydroperoxy-5'-methyl-6'-(3''-oxobutyl)cyclohex-2'-yl>propenoate
• CAS No.: 129143-90-4
• Molecular Formula: C₁₆H₂₄O₆
• Molecular Weight: 312.363
• Mol file: 129143-90-4.mol

Synonyms:methyl <1'R,2'S,5'R,6'S>-2-<1'-formyl-1'-hydroperoxy-5'-methyl-6'-(3''-oxobutyl)cyclohex-2'-yl>propenoate

Chemical Property of methyl <1'R,2'S,5'R,6'S>-2-<1'-formyl-1'-hydroperoxy-5'-methyl-6'-(3''-oxobutyl)cyclohex-2'-yl>propenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl <1'R,2'S,5'R,6'S>-2-<1'-formyl-1'-hydroperoxy-5'-methyl-6'-(3''-oxobutyl)cyclohex-2'-yl>propenoate

There total 6 articles about methyl <1'R,2'S,5'R,6'S>-2-<1'-formyl-1'-hydroperoxy-5'-methyl-6'-(3''-oxobutyl)cyclohex-2'-yl>propenoate 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: 53.0%

methyl <2'R,4a'S,5'R,8'R>-2-(2',5'-dimethyl-2'-hydroperoxy-2',3',4',4a',5',6',7',8'-octahydronaphthalen-8'-yl)propenoate (129165-35-1) → methyl <1'R,2'S,5'R,6'S>-2-<1'-formyl-1'-hydroperoxy-5'-methyl-6'-(3''-oxobutyl)cyclohex-2'-yl>propenoate (129143-90-4)

Guidance literature:

In acetonitrile; at 0 ℃; for 0.5h;

DOI:10.1039/c39900000451

Reference yield:

methyl <2'R,4a'S,5'R,8'R>-2-(2',5'-dimethyl-2'-hydroperoxy-2',3',4',4a',5',6',7',8'-octahydronaphthalen-8'-yl)propenoate (129165-35-1) → methyl <5a'S,6'R,9'S>-2-(3'H-3',6'-dimethyl-9a'-formyl-3'-hydroxyperhydro-1',2'-benzodioxepin-9'-yl)propenoate (129143-91-5) + methyl <1'R,2'S,5'R,6'S>-2-<1'-formyl-1'-hydroperoxy-5'-methyl-6'-(3''-oxobutyl)cyclohex-2'-yl>propenoate (129143-90-4)

Guidance literature:

With tris(1,10-phenanthroline)iron(III) tris(hexafluorophosphate); oxygen; copper(II) bis(trifluoromethanesulfonate); In acetonitrile; at 0 - 20 ℃; for 0.5h; Title compound not separated from byproducts;

DOI:10.1021/ja00150a009

Reference yield:

artemisinic acid (80286-58-4) → methyl <1'R,2'S,5'R,6'S>-2-<1'-formyl-1'-hydroperoxy-5'-methyl-6'-(3''-oxobutyl)cyclohex-2'-yl>propenoate (129143-90-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / K₂CO₃ / acetone / 1 h / Heating

2: 82 percent / O₂, Rose Bengal / acetonitrile / 6 h / -30 °C / Irradiation

3: O₂, Fe(phen)3(PF₆)3, Cu(OTf)2 / acetonitrile / 0.5 h / 0 - 20 °C

With tris(1,10-phenanthroline)iron(III) tris(hexafluorophosphate); oxygen; copper(II) bis(trifluoromethanesulfonate); rose bengal; potassium carbonate; In acetone; acetonitrile;

DOI:10.1021/ja00150a009

upstream raw materials:

methyl <2'R,4a'S,5'R,8'R>-2-(2',5'-dimethyl-2'-hydroperoxy-2',3',4',4a',5',6',7',8'-octahydronaphthalen-8'-yl)propenoate

artemisinic acid

methyl artemisinate

Downstream raw materials:

qinghaosu

dehydroqinghaosu

2-((1R,4S,4aR,7R,9aS)-4a-Formyl-7-methoxy-1,7-dimethyl-octahydro-5,6-dioxa-benzocyclohepten-4-yl)-acrylic acid methyl ester