(2S,3R,4aS,7aR,8aS,12aR,13aR,14aR)-2-(benzyloxy)-3-((benzyloxy)methyl)hexahydropyrano[3,2-b]pyrano-[2',3':5,6]pyrano[2,3-g]oxocine

Base Information

• Chemical Name: (2S,3R,4aS,7aR,8aS,12aR,13aR,14aR)-2-(benzyloxy)-3-((benzyloxy)methyl)hexahydropyrano[3,2-b]pyrano-[2',3':5,6]pyrano[2,3-g]oxocine
• CAS No.: 1415891-60-9
• Molecular Formula: C₃₁H₄₀O₆
• Molecular Weight: 508.655
• Mol file: 1415891-60-9.mol

Synonyms:

Chemical Property of (2S,3R,4aS,7aR,8aS,12aR,13aR,14aR)-2-(benzyloxy)-3-((benzyloxy)methyl)hexahydropyrano[3,2-b]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,7aR,8aS,12aR,13aR,14aR)-2-(benzyloxy)-3-((benzyloxy)methyl)hexahydropyrano[3,2-b]pyrano-[2',3':5,6]pyrano[2,3-g]oxocine

There total 3 articles about (2S,3R,4aS,7aR,8aS,12aR,13aR,14aR)-2-(benzyloxy)-3-((benzyloxy)methyl)hexahydropyrano[3,2-b]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: 38.0%

C31H40O7 (1415891-38-1) → (2S,3R,4aS,7aR,8aS,12aR,13aS,14aR)-2-(benzyloxy)-3-((benzyloxy)methyl)hexahydropyrano[3,2-b]pyrano-[2',3':5,6]pyrano[2,3-g]oxocine (1415891-37-0) + (2S,3R,4aS,7aR,8aS,12aR,13aR,14aR)-2-(benzyloxy)-3-((benzyloxy)methyl)hexahydropyrano[3,2-b]pyrano-[2',3':5,6]pyrano[2,3-g]oxocine (1415891-60-9)

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) → (2S,3R,4aS,7aR,8aS,12aR,13aS,14aR)-2-(benzyloxy)-3-((benzyloxy)methyl)hexahydropyrano[3,2-b]pyrano-[2',3':5,6]pyrano[2,3-g]oxocine (1415891-37-0) + (2S,3R,4aS,7aR,8aS,12aR,13aR,14aR)-2-(benzyloxy)-3-((benzyloxy)methyl)hexahydropyrano[3,2-b]pyrano-[2',3':5,6]pyrano[2,3-g]oxocine (1415891-60-9)

Guidance literature:

Multi-step reaction with 3 steps

1: boron trifluoride diethyl etherate / hexane; dichloromethane / -80 - -40 °C / Inert atmosphere; Molecular sieve

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

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

With triethylsilane; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jo302267f

Reference yield:

C40H62O7Si2 → (2S,3R,4aS,7aR,8aS,12aR,13aS,14aR)-2-(benzyloxy)-3-((benzyloxy)methyl)hexahydropyrano[3,2-b]pyrano-[2',3':5,6]pyrano[2,3-g]oxocine (1415891-37-0) + (2S,3R,4aS,7aR,8aS,12aR,13aR,14aR)-2-(benzyloxy)-3-((benzyloxy)methyl)hexahydropyrano[3,2-b]pyrano-[2',3':5,6]pyrano[2,3-g]oxocine (1415891-60-9)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

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

With triethylsilane; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;

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

C₃₁H₄₀O₇