(+)-9-Norartemisinin, 9-n-butyl-

Base Information

• Chemical Name: (+)-9-Norartemisinin, 9-n-butyl-
• CAS No.: 154698-10-9
• Molecular Formula: C₁₈H₂₈O₅
• Molecular Weight: 324.417
• Mol file: 154698-10-9.mol

Synonyms:3,12-Epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10(3H)-one,9-butyloctahydro-3,6-dimethyl-, [3R-(3a,5ab,6b,8ab,9a,12b,12aR*)]-

Chemical Property of (+)-9-Norartemisinin, 9-n-butyl-

Chemical Property:

• PSA: 53.99000
• LogP: 3.56520

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+)-9-Norartemisinin, 9-n-butyl-

There total 4 articles about (+)-9-Norartemisinin, 9-n-butyl- 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: 41.0%

dehydroqinghaosu (101020-89-7) + n-propylmagnesium bromide (927-77-5) → (+)-octahydro-9β-butyl-3,6α-dimethyl-3,12-epoxy-12H-pyrano<4,3-j>-1,2-benzodioxepin-10(3H)-one (154698-10-9) + C18H28O5 + C33H48O10

Guidance literature:

n-propylmagnesium bromide; With copper(I) bromide; In tetrahydrofuran; at -40 ℃; for 0.333333h;

(3R,5aS,6R,8aS,12S,12aR)-3,6-dimethyl-9-methyleneoctahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10(3H)-one; In tetrahydrofuran; at -78 ℃; for 2h; Further stages.;

DOI:10.1021/jm0103007

Reference yield: 27.0%

(1''S,1'''S,3''S,6''R)-(2''E)-2-<2'-<3''-(1'''-carboxypentyl)-6''-methyl-2''-<(trimethylsilyl)methylene>cyclohexyl>ethyl>-2,5,5-trimethyl-1,3-dioxane (154698-42-7) → (+)-octahydro-9β-butyl-3,6α-dimethyl-3,12-epoxy-12H-pyrano<4,3-j>-1,2-benzodioxepin-10(3H)-one (154698-10-9)

Guidance literature:

(1''S,1'''S,3''S,6''R)-(2''E)-2-<2'-<3''-(1'''-carboxypentyl)-6''-methyl-2''-<(trimethylsilyl)methylene>cyclohexyl>ethyl>-2,5,5-trimethyl-1,3-dioxane; With ozone; In dichloromethane; at -78 ℃; under 362.004 Torr;

With sulfuric acid; silica gel; In dichloromethane; at 20 ℃;

DOI:10.1021/jm020142z

Reference yield:

2,5,5-trimethyl-2-<2'-<4''-(carboxymethyl)-1''(R)-methyl-3''-<(trimethylsilyl)methylene>cyclohex-2''-yl>ethyl>-1,3-dioxane (116399-92-9) → (+)-octahydro-9β-butyl-3,6α-dimethyl-3,12-epoxy-12H-pyrano<4,3-j>-1,2-benzodioxepin-10(3H)-one (154698-10-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA / tetrahydrofuran / 2.67 h / -78 - 50 °C

1.2: 88 percent / tetrahydrofuran / 2.5 h / 0 °C

2.1: O₃ / CH₂Cl₂ / -78 °C / 362 Torr

2.2: 27 percent / 15 percent aq. H₂SO₄; silica gel / CH₂Cl₂ / 20 °C

With ozone; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm020142z

upstream raw materials:

(1''S,1'''S,3''S,6''R)-(2''E)-2-<2'-<3''-(1'''-carboxypentyl)-6''-methyl-2''-<(trimethylsilyl)methylene>cyclohexyl>ethyl>-2,5,5-trimethyl-1,3-dioxane

dehydroqinghaosu

n-propylmagnesium bromide

2,5,5-trimethyl-2-<2'-<4''-(carboxymethyl)-1''(R)-methyl-3''-<(trimethylsilyl)methylene>cyclohex-2''-yl>ethyl>-1,3-dioxane

Refernces

• 1、 Avery, Mitchell A.,Alvim-Gaston, Maria,Vroman, Jeffrey A.,Wu, Baogen,Ager, Arba,Peters, Wallace,Robinson, Brian L.,Charman, William. "Structure-activity relationships of the antimalarial agent artemisinin. 7. Direct modification of (+)-artemisinin and in vivo antimalarial screening of new, potential preclinical antimalarial candidates". . p. 4321 - 4335. Retrieved 2007/10/03.