(1R,2R,3R,12S,15R,16R)-1-acetyloxy-2,3-epoxy-12-(benzyloxycarbonyl)-9,10-[methylenebis(oxy)]galanthan-7-one

Base Information

• Chemical Name: (1R,2R,3R,12S,15R,16R)-1-acetyloxy-2,3-epoxy-12-(benzyloxycarbonyl)-9,10-[methylenebis(oxy)]galanthan-7-one
• CAS No.: 178449-40-6
• Molecular Formula: C₂₆H₂₃NO₈
• Molecular Weight: 477.471
• Mol file: 178449-40-6.mol

Synonyms:(1R,2R,3R,12S,15R,16R)-1-acetyloxy-2,3-epoxy-12-(benzyloxycarbonyl)-9,10-[methylenebis(oxy)]galanthan-7-one

Chemical Property of (1R,2R,3R,12S,15R,16R)-1-acetyloxy-2,3-epoxy-12-(benzyloxycarbonyl)-9,10-[methylenebis(oxy)]galanthan-7-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3R,12S,15R,16R)-1-acetyloxy-2,3-epoxy-12-(benzyloxycarbonyl)-9,10-[methylenebis(oxy)]galanthan-7-one

There total 15 articles about (1R,2R,3R,12S,15R,16R)-1-acetyloxy-2,3-epoxy-12-(benzyloxycarbonyl)-9,10-[methylenebis(oxy)]galanthan-7-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:

(1S,3aR,12bR,12cR)-1-Acetoxy-7-oxo-4,5,12b,12c-tetrahydro-1H,7H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-3a-carboxylic acid benzyl ester (178449-39-3) → (1R,2R,3R,12S,15R,16R)-1-acetyloxy-2,3-epoxy-12-(benzyloxycarbonyl)-9,10-[methylenebis(oxy)]galanthan-7-one (178449-40-6)

Guidance literature:

With 3,3-dimethyldioxirane; In acetone; at 0 ℃; for 96h; Yield given;

DOI:10.1021/ja9606440

Reference yield:

(2'S,6R)-1-methoxy-6-(2-hydroxyethyl)-6-<<2'-(methoxymethyl)pyrrolidinyl>carbonyl>-1,4-cyclohexadiene (151071-62-4) → (1R,2R,3R,12S,15R,16R)-1-acetyloxy-2,3-epoxy-12-(benzyloxycarbonyl)-9,10-[methylenebis(oxy)]galanthan-7-one (178449-40-6)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) Ph₃P, DEAD, 2.) (PhO)2P(O)N₃ / 1.) THF, 0 deg C, 20 min, 2.) THF, from 0 deg C to RT

2: 95 percent / aq. 6M HCl / methanol

3: 82 percent / I₂, H₂O / tetrahydrofuran / 12 h

4: 90 percent / Ph₃P / tetrahydrofuran / 9 h / Heating

5: 98 percent / Et₃N / CH₂Cl₂ / 12 h / 0 - 20 °C

6: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, from -78 deg C to RT, 5 h

7: 45 percent / Bu₃SnH, AIBN / benzene / 16 h / Heating

8: benzene / 7 h / Irradiation

9: 2.) NaBH₄ / 1.) EtOH, RT, 15 min, 2.) EtOH, RT, 1 h

10: 87 percent / NaIO₄ / tetrahydrofuran; H₂O / 12 h / Ambient temperature

11: 34 percent / H₂SO₄ / acetic acid / 0.25 h / 50 °C

12: dimethyldioxirane / acetone / 96 h / 0 °C

With hydrogenchloride; sodium tetrahydroborate; sodium periodate; n-butyllithium; 2,2'-azobis(isobutyronitrile); sulfuric acid; diphenyl phosphoryl azide; water; iodine; tri-n-butyl-tin hydride; 3,3-dimethyldioxirane; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; acetone; benzene;

DOI:10.1021/ja9606440

Reference yield:

(3aR,4R,5R)-4-iodo-2,3,6,7-tetrahydroindole-3a,5-carbolactone → (1R,2R,3R,12S,15R,16R)-1-acetyloxy-2,3-epoxy-12-(benzyloxycarbonyl)-9,10-[methylenebis(oxy)]galanthan-7-one (178449-40-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / Et₃N / CH₂Cl₂ / 12 h / 0 - 20 °C

2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 5 min, 2.) THF, hexane, from -78 deg C to RT, 5 h

3: 45 percent / Bu₃SnH, AIBN / benzene / 16 h / Heating

4: benzene / 7 h / Irradiation

5: 2.) NaBH₄ / 1.) EtOH, RT, 15 min, 2.) EtOH, RT, 1 h

6: 87 percent / NaIO₄ / tetrahydrofuran; H₂O / 12 h / Ambient temperature

7: 34 percent / H₂SO₄ / acetic acid / 0.25 h / 50 °C

8: dimethyldioxirane / acetone / 96 h / 0 °C

With sodium tetrahydroborate; sodium periodate; n-butyllithium; 2,2'-azobis(isobutyronitrile); sulfuric acid; tri-n-butyl-tin hydride; 3,3-dimethyldioxirane; triethylamine; In tetrahydrofuran; dichloromethane; water; acetic acid; acetone; benzene;

DOI:10.1021/ja9606440

upstream raw materials:

(1S,3aR,12bR,12cR)-1-Acetoxy-7-oxo-4,5,12b,12c-tetrahydro-1H,7H-[1,3]dioxolo[4,5-j]pyrrolo[3,2,1-de]phenanthridine-3a-carboxylic acid benzyl ester

(2'S,6R)-1-methoxy-6-(2-hydroxyethyl)-6-<<2'-(methoxymethyl)pyrrolidinyl>carbonyl>-1,4-cyclohexadiene

(2'S,6R)-1-methoxy-6-(2-azidoethyl)-6-<<2'-(methoxymethyl)pyrrolidinyl>carbonyl>-1,4-cyclohexadiene

(3aS,4S,5R)-N-(piperonyloyl)-4,5-epoxy-5,6-dihydro-4H-3a-(benzyloxycarbonyl)indoline