(4aS,5aR,7aS,8aR,12R,13aS,14aR,15aS,16aR)-12-(((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)octahydropyrano[3,2-b]pyran-2-yl)methyl)hexadecahydro-2H-pyrano[2',3':5,6]pyrano[2,3-f]-pyrano[3,2-b:5,6-b']bis(oxepine)-11(12H)-one

Base Information

• Chemical Name: (4aS,5aR,7aS,8aR,12R,13aS,14aR,15aS,16aR)-12-(((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)octahydropyrano[3,2-b]pyran-2-yl)methyl)hexadecahydro-2H-pyrano[2',3':5,6]pyrano[2,3-f]-pyrano[3,2-b:5,6-b']bis(oxepine)-11(12H)-one
• CAS No.: 1415891-46-1
• Molecular Formula: C₄₉H₇₀O₁₁Si
• Molecular Weight: 863.174
• Mol file: 1415891-46-1.mol

Synonyms:

Chemical Property of (4aS,5aR,7aS,8aR,12R,13aS,14aR,15aS,16aR)-12-(((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)octahydropyrano[3,2-b]pyran-2-yl)methyl)hexadecahydro-2H-pyrano[2',3':5,6]pyrano[2,3-f]-pyrano[3,2-b:5,6-b']bis(oxepine)-11(12H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4aS,5aR,7aS,8aR,12R,13aS,14aR,15aS,16aR)-12-(((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)octahydropyrano[3,2-b]pyran-2-yl)methyl)hexadecahydro-2H-pyrano[2',3':5,6]pyrano[2,3-f]-pyrano[3,2-b:5,6-b']bis(oxepine)-11(12H)-one

There total 9 articles about (4aS,5aR,7aS,8aR,12R,13aS,14aR,15aS,16aR)-12-(((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)octahydropyrano[3,2-b]pyran-2-yl)methyl)hexadecahydro-2H-pyrano[2',3':5,6]pyrano[2,3-f]-pyrano[3,2-b:5,6-b']bis(oxepine)-11(12H)-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:

C52H78O11Si2 → (4aS,5aR,7aS,8aR,12R,13aS,14aR,15aS,16aR)-12-(((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)octahydropyrano[3,2-b]pyran-2-yl)methyl)hexadecahydro-2H-pyrano[2',3':5,6]pyrano[2,3-f]-pyrano[3,2-b:5,6-b']bis(oxepine)-11(12H)-one (1415891-46-1)

Guidance literature:

With pyridinium p-toluenesulfonate; In methanol; dichloromethane; at 20 ℃; for 3.5h; Inert atmosphere;

DOI:10.1021/jo302267f

Reference yield:

(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 (1415891-31-4) → (4aS,5aR,7aS,8aR,12R,13aS,14aR,15aS,16aR)-12-(((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)octahydropyrano[3,2-b]pyran-2-yl)methyl)hexadecahydro-2H-pyrano[2',3':5,6]pyrano[2,3-f]-pyrano[3,2-b:5,6-b']bis(oxepine)-11(12H)-one (1415891-46-1)

Guidance literature:

Multi-step reaction with 9 steps

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

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

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

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

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

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

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

8: boron trifluoride diethyl etherate / hexane; dichloromethane / 3 h / -80 °C / Inert atmosphere; Molecular sieve

9: pyridinium p-toluenesulfonate / dichloromethane; methanol / 3.5 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; 10 wt% Pd(OH)2 on carbon; boron trifluoride diethyl etherate; hydrogen; pyridinium p-toluenesulfonate; 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;

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) → (4aS,5aR,7aS,8aR,12R,13aS,14aR,15aS,16aR)-12-(((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)octahydropyrano[3,2-b]pyran-2-yl)methyl)hexadecahydro-2H-pyrano[2',3':5,6]pyrano[2,3-f]-pyrano[3,2-b:5,6-b']bis(oxepine)-11(12H)-one (1415891-46-1)

Guidance literature:

Multi-step reaction with 10 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: boron trifluoride diethyl etherate / hexane; dichloromethane / 3 h / -80 °C / Inert atmosphere; Molecular sieve

10: pyridinium p-toluenesulfonate / dichloromethane; methanol / 3.5 h / 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; triethylsilane; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; 10 wt% Pd(OH)2 on carbon; boron trifluoride diethyl etherate; hydrogen; pyridinium p-toluenesulfonate; 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;

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

Downstream raw materials:

(2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,20aS,21aR,22aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-octacosahydropyrano[3,2-b]pyrano[2,3-j:6,5-j']bis(pyrano[2',3':5,6]pyrano[3,2-b]oxepine)

(4aS,5aR,7aS,8aR,13R,14aS,15aR,16aS,17aR)-13-(((2S,3R,4aS,6R,7S,8aR)-7-(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)octahydropyrano[3,2-b]pyran-2-yl)methyl)octadecahydropyrano[2''',3''':5'',6'']pyrano[2'',3'':6',7']oxepino[2',3':5,6]pyrano[3,2-b]oxocin-12(13H)-one

(2R,3S,4aR,5aS,6aR,7aS,8aR,9aS,10aR,14aS,15aR,17aS,18aR,20aS,21aR,22aS)-3-(benzyloxy)-2-((benzyloxy)methyl)-20a-methoxyoctacosahydropyrano[3,2-b]pyrano[2,3-j:6,5-j']bis(pyrano[2',3':5,6]pyrano[3,2-b]oxepine)

(2S,3R,4aS,5aR,6aS,9aR,10aS,12aR,13aS,17aR,18aS,19aR,20aS,21aR,22aS,23aR)-2-(benzyloxy)-3-((benzyloxy)methyl)octacosahydro-1H-pyrano[2''',3''':5'',6'']pyrano[2'',3'':6',7']oxepino[2',3':5,6]pyrano[3,2-b]pyrano[2'',3'':5',6']pyrano[2',3':5,6]pyrano[2,3-g]oxocine