(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

Base Information

• Chemical Name: (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
• CAS No.: 1415891-31-4
• Molecular Formula: C₃₀H₃₈O₆
• Molecular Weight: 494.628
• Mol file: 1415891-31-4.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 2 articles about (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 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: 92.0%

(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,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)

Guidance literature:

With triethylsilane; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 0.5h; 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) → (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)

Guidance literature:

Multi-step reaction with 2 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

With triethylsilane; trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; In dichloromethane; chloroform;

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

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

Downstream raw materials:

C₆₀H₈₈O₁₃SSi₂

C₅₄H₇₄O₁₃SSi

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

C₄₈H₆₉BrO₁₁Si