(2S,3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-2-Hydroxy-5,11-dimethoxy-11c-(4-methoxy-benzyloxymethyl)-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracen-1-one

Base Information

• Chemical Name: (2S,3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-2-Hydroxy-5,11-dimethoxy-11c-(4-methoxy-benzyloxymethyl)-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracen-1-one
• CAS No.: 125458-69-7
• Molecular Formula: C₃₀H₄₄O₇
• Molecular Weight: 516.675
• Mol file: 125458-69-7.mol

Synonyms:(2S,3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-2-Hydroxy-5,11-dimethoxy-11c-(4-methoxy-benzyloxymethyl)-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracen-1-one

Chemical Property of (2S,3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-2-Hydroxy-5,11-dimethoxy-11c-(4-methoxy-benzyloxymethyl)-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracen-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-2-Hydroxy-5,11-dimethoxy-11c-(4-methoxy-benzyloxymethyl)-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracen-1-one

There total 9 articles about (2S,3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-2-Hydroxy-5,11-dimethoxy-11c-(4-methoxy-benzyloxymethyl)-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracen-1-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: 86.0%

(1R,3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-1-Hydroxy-5,11-dimethoxy-11c-(4-methoxy-benzyloxymethyl)-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracen-2-one (125458-68-6) → (2S,3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-2-Hydroxy-5,11-dimethoxy-11c-(4-methoxy-benzyloxymethyl)-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracen-1-one (125458-69-7)

Guidance literature:

With sodium methylate; In methanol; dimethyl sulfoxide; at 85 ℃;

DOI:10.1016/S0040-4039(00)99255-4

Reference yield:

(+)-<4aR-(4aβ,5β,8α,8aα)>-4a,5,6,7,8,8a-hexahydro-4a,8-dimethyl-3-formyl-5-methoxy-2(1H)-naphthalenone (123929-85-1) → (2S,3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-2-Hydroxy-5,11-dimethoxy-11c-(4-methoxy-benzyloxymethyl)-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracen-1-one (125458-69-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 75 percent / H₂O / 3 h

2: sodium borohydride / tetrahydrofuran; H₂O

3: 1) i-Bu₂AlH 2) cc.HCl / 1) THF, -40 deg C

4: 88 percent / sodium hydride / tetrahydrofuran; hexamethylphosphoric acid triamide / 14 h / 70 °C

6: 71 percent / osmium tetroxide / pyridine

7: 97 percent / Swern oxidation

8: 86 percent / sodium methoxide / dimethylsulfoxide; methanol / 85 °C

With hydrogenchloride; sodium tetrahydroborate; osmium(VIII) oxide; sodium methylate; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; water; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)99255-4

Reference yield:

((3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-5,11-Dimethoxy-3,8,11a-trimethyl-1,4,5,6a,7,7a,8,9,10,11,11a,11b-dodecahydro-3aH-6-oxa-benzo[de]anthracen-11c-yl)-methanol (125458-64-2) → (2S,3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-2-Hydroxy-5,11-dimethoxy-11c-(4-methoxy-benzyloxymethyl)-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracen-1-one (125458-69-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 88 percent / sodium hydride / tetrahydrofuran; hexamethylphosphoric acid triamide / 14 h / 70 °C

3: 71 percent / osmium tetroxide / pyridine

4: 97 percent / Swern oxidation

5: 86 percent / sodium methoxide / dimethylsulfoxide; methanol / 85 °C

With osmium(VIII) oxide; sodium methylate; sodium hydride; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)99255-4

upstream raw materials:

(1R,3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-1-Hydroxy-5,11-dimethoxy-11c-(4-methoxy-benzyloxymethyl)-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracen-2-one

(+)-<4aR-(4aβ,5β,8α,8aα)>-4a,5,6,7,8,8a-hexahydro-4a,8-dimethyl-3-formyl-5-methoxy-2(1H)-naphthalenone

((3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-5,11-Dimethoxy-3,8,11a-trimethyl-1,4,5,6a,7,7a,8,9,10,11,11a,11b-dodecahydro-3aH-6-oxa-benzo[de]anthracen-11c-yl)-methanol

(+)-(1β,9β)-20-hydroxy-1-methoxypicras-12-en-16-one