Bis[1,3]dioxolo[4,5-c:4',5'-j]phenanthridin-5(3aH)-one,3b,4,12,12a-tetrahydro-6,12-dihydroxy-2,2-dimethyl-, (3aS,3bR,12S,12aR)-

Base Information

• Chemical Name: Bis[1,3]dioxolo[4,5-c:4',5'-j]phenanthridin-5(3aH)-one,3b,4,12,12a-tetrahydro-6,12-dihydroxy-2,2-dimethyl-, (3aS,3bR,12S,12aR)-
• CAS No.: 40041-97-2
• Molecular Formula: C17H17 N O7
• Molecular Weight: 347.324
• Mol file: 40041-97-2.mol

Synonyms:Bis[1,3]dioxolo[4,5-c:4',5'-j]phenanthridin-5(3aH)-one,3b,4,12,12a-tetrahydro-6,12-dihydroxy-2,2-dimethyl-, [3aS-(3aa,3bb,12a,12aa)]-;3,4-Di-O-isopropylidenenarciclasine; Narciclasine acetonide

Chemical Property of Bis[1,3]dioxolo[4,5-c:4',5'-j]phenanthridin-5(3aH)-one,3b,4,12,12a-tetrahydro-6,12-dihydroxy-2,2-dimethyl-, (3aS,3bR,12S,12aR)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Bis[1,3]dioxolo[4,5-c:4',5'-j]phenanthridin-5(3aH)-one,3b,4,12,12a-tetrahydro-6,12-dihydroxy-2,2-dimethyl-, (3aS,3bR,12S,12aR)-

There total 4 articles about Bis[1,3]dioxolo[4,5-c:4',5'-j]phenanthridin-5(3aH)-one,3b,4,12,12a-tetrahydro-6,12-dihydroxy-2,2-dimethyl-, (3aS,3bR,12S,12aR)- 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: 97.0%

narciclasine (29477-83-6,220751-83-7) + 2,2-dimethoxy-propane (77-76-9) → (2S,5aS,2aR,5bR)-2,8-dihydroxy-4,4-dimethyl-2,6,2a,5a,5b-pentahydro-10H-1,3-dioxolano<4,5-c>1,3-dioxoleno<4,5-j>phenanthridin-7-one (40041-97-2)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 20 ℃; for 16h;

DOI:10.1021/jo000710n DOI:10.3987/com-01-s(k)7

Reference yield: 74.0%

2,2-dimethoxypropane (558-18-9) + narciclasine (29477-83-6,220751-83-7) → (2S,5aS,2aR,5bR)-2,8-dihydroxy-4,4-dimethyl-2,6,2a,5a,5b-pentahydro-10H-1,3-dioxolano<4,5-c>1,3-dioxoleno<4,5-j>phenanthridin-7-one (40041-97-2)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 25 ℃; for 12h;

Reference yield: 38.0%

methyl 6-<(3aS,4R,7R,7aR)-7-hydroxy-2,2-dimethyl-4-<(phenylmethoxy)amino>-6-phenylthio-2,3,4,7,3a,7a-hexahydro-1,3-dioxainden-5-yl>-4-methoxy-2H-benzo1,3-dioxolene-5-carboxylate (235757-42-3) → (2S,5aS,2aR,5bR)-2,8-dihydroxy-4,4-dimethyl-2,6,2a,5a,5b-pentahydro-10H-1,3-dioxolano<4,5-c>1,3-dioxoleno<4,5-j>phenanthridin-7-one (40041-97-2) + (5aS,2R,2aR,5bR)-2,8-dihydroxy-4,4-dimethyl-1-phenylthio-2,6,2a,5a,5b-pentahydro-10H-1,3-dioxolano<4,5-c>1,3-dioxoleno<4,5-j>phenanthridin-7-one

Guidance literature:

With samarium diiodide; In tetrahydrofuran; for 44h;

DOI:10.1021/ja9826688

upstream raw materials:

narciclasine

acetone

methyl 6-<(3aS,4R,7R,7aR)-7-hydroxy-2,2-dimethyl-4-<(phenylmethoxy)amino>-6-phenylthio-2,3,4,7,3a,7a-hexahydro-1,3-dioxainden-5-yl>-4-methoxy-2H-benzo1,3-dioxolene-5-carboxylate

2,2-dimethoxy-propane

Downstream raw materials:

narciclasine

4,7-dihydroxy-[1,3]dioxolo[4,5-j]phenanthridin-6(5H)-one

(3aS)-6-hydroxy-2,2-dimethyl-(3ar,12ac)-3a,4,11,12a-tetrahydro-bis[1,3]dioxolo[4,5-c;4',5'-j]phenanthridine-5,12-dione

C₂₄H₂₁NO₈