(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

Base Information

• Chemical Name: (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
• CAS No.: 1415891-22-3
• Molecular Formula: C₄₄H₅₈O₁₀
• Molecular Weight: 746.939
• Mol file: 1415891-22-3.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 16 articles about (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 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:

(2S,3R,4aS,5aR,6aS,9aR,10aS,12aR,13aS,17aR,18aS,19aR,20aS,21aR,22aS,23aR)-2-(benzyloxy)-3-((benzyloxy)methyl)-5a-methoxyoctacosahydro-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 → (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 (1415891-22-3)

Guidance literature:

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

DOI:10.1021/jo302267f

Reference yield:

(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 (1415891-30-3) → (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 (1415891-22-3)

Guidance literature:

Multi-step reaction with 16 steps

1: toluene-4-sulfonic acid / chloroform / 7 h / 55 °C / Inert atmosphere

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

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

4: 2,6-dimethylpyridine / tetrahydrofuran / 0.5 h / -80 °C / Inert atmosphere

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

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

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

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

9: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 20 °C

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

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

12: boron trifluoride diethyl etherate / hexane; dichloromethane / 4 h / -40 °C / Inert atmosphere; Molecular sieve

13: pyridinium p-toluenesulfonate / chloroform; methanol / 23 h / 20 - 60 °C

14: pyridinium p-toluenesulfonate / methanol; 1,2-dichloro-ethane / 5.5 h / 55 °C / Inert atmosphere

15: methanol; 1,2-dichloro-ethane / 2 h / 55 °C / Inert atmosphere

16: trimethylsilyl trifluoromethanesulfonate; triethylsilane / dichloromethane / 1 h / 0 °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; chloroform; ethyl acetate; 1,2-dichloro-ethane;

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) → (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 (1415891-22-3)

Guidance literature:

Multi-step reaction with 14 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

10: boron trifluoride diethyl etherate / hexane; dichloromethane / 4 h / -40 °C / Inert atmosphere; Molecular sieve

11: pyridinium p-toluenesulfonate / chloroform; methanol / 23 h / 20 - 60 °C

12: pyridinium p-toluenesulfonate / methanol; 1,2-dichloro-ethane / 5.5 h / 55 °C / Inert atmosphere

13: methanol; 1,2-dichloro-ethane / 2 h / 55 °C / Inert atmosphere

14: trimethylsilyl trifluoromethanesulfonate; triethylsilane / dichloromethane / 1 h / 0 °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; chloroform; ethyl acetate; 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