(2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,19aS,20aR,21aS)-3-(benzyloxy)-2-((benzyloxy)methyl)hexacosahydro-2H-pyrano[2''' ',3''' ':5''',6''']pyrano[2''',3''':5'',6'']pyrano[2'',3'':5',6']pyrano[2',3':5,6]pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin

Base Information

• Chemical Name: (2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,19aS,20aR,21aS)-3-(benzyloxy)-2-((benzyloxy)methyl)hexacosahydro-2H-pyrano[2''' ',3''' ':5''',6''']pyrano[2''',3''':5'',6'']pyrano[2'',3'':5',6']pyrano[2',3':5,6]pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin
• CAS No.: 1415891-43-8
• Molecular Formula: C₄₂H₅₄O₁₀
• Molecular Weight: 718.885

Synonyms:(2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,19aS,20aR,21aS)-3-(benzyloxy)-2-((benzyloxy)methyl)hexacosahydro-2H-pyrano[2''' ',3''' ':5''',6''']pyrano[2''',3''':5'',6'']pyrano[2'',3'':5',6']pyrano[2',3':5,6]pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin

Chemical Property of (2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,19aS,20aR,21aS)-3-(benzyloxy)-2-((benzyloxy)methyl)hexacosahydro-2H-pyrano[2''' ',3''' ':5''',6''']pyrano[2''',3''':5'',6'']pyrano[2'',3'':5',6']pyrano[2',3':5,6]pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,19aS,20aR,21aS)-3-(benzyloxy)-2-((benzyloxy)methyl)hexacosahydro-2H-pyrano[2''' ',3''' ':5''',6''']pyrano[2''',3''':5'',6'']pyrano[2'',3'':5',6']pyrano[2',3':5,6]pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin

There total 13 articles about (2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,19aS,20aR,21aS)-3-(benzyloxy)-2-((benzyloxy)methyl)hexacosahydro-2H-pyrano[2''' ',3''' ':5''',6''']pyrano[2''',3''':5'',6'']pyrano[2'',3'':5',6']pyrano[2',3':5,6]pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin 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: 99.0%

(2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,19aS,20aR,21aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-19a-methoxyhexacosahydro-2H-pyrano[2''' ',3''' ':5''',6''']pyrano[2''',3''':5'',6'']pyrano[2'',3'':5',6']pyrano[2',3':5,6]pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin (1415891-42-7) → (2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,19aS,20aR,21aS)-3-(benzyloxy)-2-((benzyloxy)methyl)hexacosahydro-2H-pyrano[2''' ',3''' ':5''',6''']pyrano[2''',3''':5'',6'']pyrano[2'',3'':5',6']pyrano[2',3':5,6]pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin (1415891-43-8)

Guidance literature:

With triethylsilane; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/jo302267f

Reference yield:

(2R,3S,4aR,5aS,6aR,10aS,11aR,13aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-11a-methoxytetradecahydro-2H-pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepine (1415891-57-4) → (2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,19aS,20aR,21aS)-3-(benzyloxy)-2-((benzyloxy)methyl)hexacosahydro-2H-pyrano[2''' ',3''' ':5''',6''']pyrano[2''',3''':5'',6'']pyrano[2'',3'':5',6']pyrano[2',3':5,6]pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin (1415891-43-8)

Guidance literature:

Multi-step reaction with 11 steps

1: trimethylsilyl trifluoromethanesulfonate; triethylsilane / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

2: hydrogen; 10 wt% Pd(OH)2 on carbon / ethyl acetate / 18 h / 20 °C

3: 2,6-dimethylpyridine / tetrahydrofuran / 0.5 h / -80 °C / Inert atmosphere

4: tetrahydrofuran / 0.67 h / -80 °C / Inert atmosphere

5: n-butyllithium; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran; hexane / -100 °C / Inert atmosphere

6: toluene-4-sulfonic acid / dichloromethane; methanol / 1 h / 20 °C / Inert atmosphere

7: magnesium bromide diethyl etherate; lithium bromide / dichloromethane / 2.5 h / -15 - -5 °C

8: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 20 °C

9: toluene-4-sulfonic acid / methanol; 1,2-dichloro-ethane / 15 h / 80 °C / Inert atmosphere

10: methanol; 1,2-dichloro-ethane / 3 h / 80 °C / Inert atmosphere

11: trimethylsilyl trifluoromethanesulfonate; triethylsilane / dichloromethane / 1 h / 0 °C

With 2,6-dimethylpyridine; triethylsilane; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; 10 wt% Pd(OH)2 on carbon; hydrogen; magnesium bromide diethyl etherate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium bromide; In tetrahydrofuran; methanol; hexane; dichloromethane; ethyl acetate; 1,2-dichloro-ethane;

DOI:10.1021/jo302267f

Reference yield:

3-((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-(t-butyldimethylsiloxy)octahydropyrano[3,2-b]pyran-2-yl)prop-1-en-1-yl phenyl sulfone → (2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,19aS,20aR,21aS)-3-(benzyloxy)-2-((benzyloxy)methyl)hexacosahydro-2H-pyrano[2''' ',3''' ':5''',6''']pyrano[2''',3''':5'',6'']pyrano[2'',3'':5',6']pyrano[2',3':5,6]pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepin (1415891-43-8)

Guidance literature:

Multi-step reaction with 8 steps

1: potassium tert-butylate; tert.-butylhydroperoxide / tetrahydrofuran / -78 - -25 °C / Inert atmosphere

2: n-butyllithium; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran; hexane / -100 °C / Inert atmosphere

3: toluene-4-sulfonic acid / dichloromethane; methanol / 1 h / 20 °C / Inert atmosphere

4: magnesium bromide diethyl etherate; lithium bromide / dichloromethane / 2.5 h / -15 - -5 °C

5: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 20 °C

6: toluene-4-sulfonic acid / methanol; 1,2-dichloro-ethane / 15 h / 80 °C / Inert atmosphere

7: methanol; 1,2-dichloro-ethane / 3 h / 80 °C / Inert atmosphere

8: trimethylsilyl trifluoromethanesulfonate; triethylsilane / dichloromethane / 1 h / 0 °C

With triethylsilane; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; potassium tert-butylate; magnesium bromide diethyl etherate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium bromide; In tetrahydrofuran; methanol; hexane; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1021/jo302267f

upstream raw materials:

(2S,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-2-(((2R,3S)-3-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)methyl)hexahydropyrano[3,2-b]pyran-3(2H)-one

(2R,3S,4aR,5aS,6aR,10aS,11aR,13aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-11a-methoxytetradecahydro-2H-pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepine

(2R,3S,4aR,5aS,6aR,10aS,11aR,13aS)-3-(benzyloxy)-2-((benzyloxy)methyl)tetradecahydro-2H-pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepine

3-((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-(t-butyldimethylsiloxy)octahydropyrano[3,2-b]pyran-2-yl)-1,2-epoxypropan-1-yl phenyl sulfone

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