6,12-dihydroxy-2,2-dimethyl-3b,4,10b,11,12,12a-hexahydro-3aH-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-5-one

Base Information

• Chemical Name: 6,12-dihydroxy-2,2-dimethyl-3b,4,10b,11,12,12a-hexahydro-3aH-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-5-one
• CAS No.: 55659-25-1
• Molecular Formula: C₁₇H₁₉NO₇
• Molecular Weight: 349.34

Synonyms:6,12-dihydroxy-2,2-dimethyl-3b,4,10b,11,12,12a-hexahydro-3aH-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-5-one

Chemical Property of 6,12-dihydroxy-2,2-dimethyl-3b,4,10b,11,12,12a-hexahydro-3aH-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-5-one

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Technology Process of 6,12-dihydroxy-2,2-dimethyl-3b,4,10b,11,12,12a-hexahydro-3aH-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-5-one

There total 2 articles about 6,12-dihydroxy-2,2-dimethyl-3b,4,10b,11,12,12a-hexahydro-3aH-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-5-one 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:

narciclasine (29477-83-6,220751-83-7) → 6,12-dihydroxy-2,2-dimethyl-3b,4,10b,11,12,12a-hexahydro-3aH-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-5-one (55659-25-1)

Guidance literature:

Multi-step reaction with 3 steps

1: (i) H₂, CaCO₃, Pd, EtOH, (ii) /BRN= 385737/, Py

2: Ba(OH)2 / ethanol

3: HC(OEt)3, TsOH

With barium dihydroxide; toluene-4-sulfonic acid; orthoformic acid triethyl ester; In ethanol;

Reference yield:

(4aR)-2t,3c,4c,7-tetrahydroxy-(4ar,11bξ)-1,3,4,4a,5,11b-hexahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one (1194273-32-9) + 2,2-dimethoxy-propane (77-76-9) → 6,12-dihydroxy-2,2-dimethyl-3b,4,10b,11,12,12a-hexahydro-3aH-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-5-one (55659-25-1) + 6,12-dihydroxy-2,2-dimethyl-3b,4,10b,11,12,12a-hexahydro-3aH-1,3,7,9-tetraoxa-4-aza-dicyclopenta[a,h]phenanthren-5-one (40042-08-8)

Guidance literature:

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

DOI:10.1021/jm8013585

upstream raw materials:

narciclasine

(4aR)-2t,3c,4c,7-tetrahydroxy-(4ar,11bξ)-1,3,4,4a,5,11b-hexahydro-2H-[1,3]dioxolo[4,5-j]phenanthridin-6-one

2,2-dimethoxy-propane

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