(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)

Base Information

Chemical Name:(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)
CAS No.:1415891-67-6
Molecular Formula:C₄₄H₅₈O₁₁
Molecular Weight:762.938
Hs Code.:

(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)

Synonyms:(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)

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Chemical Property of (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)

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Technology Process of (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)

There total 13 articles about (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) 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:

: 1415891-30-3
(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

: 1415891-67-6
(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)

Guidance literature:: Multi-step reaction with 13 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: toluene-4-sulfonic acid / methanol; 1,2-dichloro-ethane / 17 h / 80 °C / Inert atmosphere

13: methanol; 1,2-dichloro-ethane / 4 h / 80 °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:

: 1415891-31-4
(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

: 1415891-67-6
(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)

Guidance literature:: Multi-step reaction with 11 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: toluene-4-sulfonic acid / methanol; 1,2-dichloro-ethane / 17 h / 80 °C / Inert atmosphere

11: methanol; 1,2-dichloro-ethane / 4 h / 80 °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; 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

: 1415891-67-6
(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)

Guidance literature:: Multi-step reaction with 9 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: boron trifluoride diethyl etherate / hexane; dichloromethane / 3 h / -80 °C / Inert atmosphere; Molecular sieve

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

8: toluene-4-sulfonic acid / methanol; 1,2-dichloro-ethane / 17 h / 80 °C / Inert atmosphere

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

With tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; boron trifluoride diethyl etherate; potassium tert-butylate; 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; 1,2-dichloro-ethane;
DOI:10.1021/jo302267f