((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-2,2-dimethyl-4-((2-nitrophenyl)ethynyl)-tetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methyl acetate

Base Information

Chemical Name:((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-2,2-dimethyl-4-((2-nitrophenyl)ethynyl)-tetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methyl acetate
CAS No.:1413282-19-5
Molecular Formula:C₂₆H₂₇NO₈
Molecular Weight:481.502
Hs Code.:

Synonyms:((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-2,2-dimethyl-4-((2-nitrophenyl)ethynyl)-tetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methyl acetate

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Chemical Property of ((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-2,2-dimethyl-4-((2-nitrophenyl)ethynyl)-tetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methyl acetate

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Technology Process of ((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-2,2-dimethyl-4-((2-nitrophenyl)ethynyl)-tetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methyl acetate

There total 6 articles about ((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-2,2-dimethyl-4-((2-nitrophenyl)ethynyl)-tetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methyl acetate 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: 95.0%

: 1413282-18-4
((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-2,2-dimethyl-4-((2-nitrophenyl)ethynyl)-tetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methanol

: 108-24-7
acetic anhydride

: 1413282-19-5
((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-2,2-dimethyl-4-((2-nitrophenyl)ethynyl)-tetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methyl acetate

Guidance literature:: With pyridine; dmap; at 20 ℃; for 2h;
DOI:10.1021/jo302198v

Reference yield:

: 1413282-16-2
(3aS,4R,6R,6aR)-6-((benzyloxy)methyl)-3a-(((tert-butyldimethylsilyl)oxy)methyl)-2,2-dimethyldihydrofuro[3,4-d]-[1,3]dioxol-4(3aH)-one

: 1413282-19-5
((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-2,2-dimethyl-4-((2-nitrophenyl)ethynyl)-tetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methyl acetate

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrahydrofuran / -78 - -10 °C

1.2: Enzymatic reaction

1.3: 4 h / 0 °C

2.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine; triethylamine / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

3.1: pyridine; dmap / 2 h / 20 °C

With pyridine; dmap; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; In tetrahydrofuran; 2.1: |Sonogashira Cross-Coupling;
DOI:10.1021/jo302198v

Reference yield:

: 198969-39-0
5-O-benzyl-2,3-O-isopropylidene-D-ribofuranose

: 1413282-19-5
((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-2,2-dimethyl-4-((2-nitrophenyl)ethynyl)-tetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methyl acetate

Guidance literature:: Multi-step reaction with 6 steps

1.1: potassium carbonate / methanol / 30 h / 90 °C

2.1: triethylamine / dichloromethane / 0 - 20 °C

3.1: Ag₂CO₃ impregnated on Celite / toluene / 3 h / Reflux

4.1: tetrahydrofuran / -78 - -10 °C

4.2: Enzymatic reaction

4.3: 4 h / 0 °C

5.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triphenylphosphine; triethylamine / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

6.1: pyridine; dmap / 2 h / 20 °C

With pyridine; dmap; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; Ag₂CO₃ impregnated on Celite; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; toluene; 5.1: |Sonogashira Cross-Coupling;
DOI:10.1021/jo302198v