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

Base Information

Chemical Name:(((3aS,4R,6R,6aR)-6-((benzyloxy)methyl)-2,2-dimethyl-4-((2-nitrophenyl)ethynyl)-tetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)-methoxy)(tert-butyl)dimethylsilane
CAS No.:1413282-11-7
Molecular Formula:C₃₀H₃₉NO₇Si
Molecular Weight:553.728
Hs Code.:

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

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

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

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

There total 5 articles about (((3aS,4R,6R,6aR)-6-((benzyloxy)methyl)-2,2-dimethyl-4-((2-nitrophenyl)ethynyl)-tetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)-methoxy)(tert-butyl)dimethylsilane 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: 85.0%

: 609-73-4
o-nitroiodobenzene

: 1413282-22-0
(((3aS,4S,6R,6aR)-6-((benzyloxy)methyl)-4-ethynyl-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)methoxy)(tert-butyl)dimethylsilane

: 1413282-11-7
(((3aS,4R,6R,6aR)-6-((benzyloxy)methyl)-2,2-dimethyl-4-((2-nitrophenyl)ethynyl)-tetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)-methoxy)(tert-butyl)dimethylsilane

Guidance literature:: With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere;
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

: 1413282-11-7
(((3aS,4R,6R,6aR)-6-((benzyloxy)methyl)-2,2-dimethyl-4-((2-nitrophenyl)ethynyl)-tetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)-methoxy)(tert-butyl)dimethylsilane

Guidance literature:: Multi-step reaction with 2 steps

1.1: tetrahydrofuran / -78 - -10 °C

1.2: Enzymatic reaction

1.3: 4 h / 20 °C

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

With 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

: 1413282-11-7
(((3aS,4R,6R,6aR)-6-((benzyloxy)methyl)-2,2-dimethyl-4-((2-nitrophenyl)ethynyl)-tetrahydrofuro[3,4-d][1,3]dioxol-3a-yl)-methoxy)(tert-butyl)dimethylsilane

Guidance literature:: Multi-step reaction with 5 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 / 20 °C

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

With 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