(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

Base Information

• Chemical Name: (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
• CAS No.: 1415891-57-4
• Molecular Formula: C₃₁H₄₀O₇
• Molecular Weight: 524.654
• Mol file: 1415891-57-4.mol

Synonyms:(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

Chemical Property of (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

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)-11a-methoxytetradecahydro-2H-pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepine

There total 1 articles about (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 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: 94.0%

methanol (67-56-1) + (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)-11a-methoxytetradecahydro-2H-pyrano[3,2-b]pyrano[2',3':5,6]pyrano[2,3-f]oxepine (1415891-57-4)

Guidance literature:

With toluene-4-sulfonic acid; In chloroform; at 55 ℃; for 7h; Inert atmosphere;

DOI:10.1021/jo302267f

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:

(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,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 (1415891-41-6)

Guidance literature:

Multi-step reaction with 8 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

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;

DOI:10.1021/jo302267f

upstream raw materials:

methanol

(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

Downstream raw materials:

(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

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