dibenzyl 2-(((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl)malonate

Base Information

• Chemical Name: dibenzyl 2-(((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl)malonate
• CAS No.: 1607447-59-5
• Molecular Formula: C₃₂H₃₄O₈
• Molecular Weight: 546.617
• Mol file: 1607447-59-5.mol

Synonyms:dibenzyl 2-(((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl)malonate

Chemical Property of dibenzyl 2-(((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl)malonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dibenzyl 2-(((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl)malonate

There total 6 articles about dibenzyl 2-(((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl)malonate 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: 50.0%

malonic acid dibenzyl ester (15014-25-2) + ((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl trifluoromethanesulphonate (895558-57-3) → dibenzyl 2-(((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl)malonate (1607447-59-5)

Guidance literature:

malonic acid dibenzyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -80 ℃; for 0.5h;

((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl trifluoromethanesulphonate; In tetrahydrofuran; at -80 - 20 ℃; for 2.83h;

DOI:10.1016/j.carres.2014.01.004

Reference yield:

(3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (114738-04-4) → dibenzyl 2-(((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl)malonate (1607447-59-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / 3 h / 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h

3.1: 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 0.5 h / -70 - 0 °C

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -80 °C

4.2: 2.83 h / -80 - 20 °C

With 2,6-di-tert-butyl-4-methylpyridine; tetrabutyl ammonium fluoride; sodium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.carres.2014.01.004

Reference yield:

(((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methoxy)(tert-butyl)diphenylsilane (168103-00-2) → dibenzyl 2-(((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl)malonate (1607447-59-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h

2.1: 2,6-di-tert-butyl-4-methylpyridine / dichloromethane / 0.5 h / -70 - 0 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -80 °C

3.2: 2.83 h / -80 - 20 °C

With 2,6-di-tert-butyl-4-methylpyridine; tetrabutyl ammonium fluoride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.carres.2014.01.004

upstream raw materials:

(3aS,5R,6R,6aS)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol

(((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methoxy)(tert-butyl)diphenylsilane

((3aS,5R,6R,6aS)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

D-arabinofuranose