(1R,2R,5S)-2-acetamido-3-(benzo[d][1,3]dioxol-5-yl)-5-((tertbutyldimethylsilyl)oxy)cyclohex-3-en-1-yl acetate

Base Information

Chemical Name:(1R,2R,5S)-2-acetamido-3-(benzo[d][1,3]dioxol-5-yl)-5-((tertbutyldimethylsilyl)oxy)cyclohex-3-en-1-yl acetate
CAS No.:1374215-48-1
Molecular Formula:C₂₃H₃₃NO₆Si
Molecular Weight:447.604
Hs Code.:

Synonyms:(1R,2R,5S)-2-acetamido-3-(benzo[d][1,3]dioxol-5-yl)-5-((tertbutyldimethylsilyl)oxy)cyclohex-3-en-1-yl acetate

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Chemical Property of (1R,2R,5S)-2-acetamido-3-(benzo[d][1,3]dioxol-5-yl)-5-((tertbutyldimethylsilyl)oxy)cyclohex-3-en-1-yl acetate

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Technology Process of (1R,2R,5S)-2-acetamido-3-(benzo[d][1,3]dioxol-5-yl)-5-((tertbutyldimethylsilyl)oxy)cyclohex-3-en-1-yl acetate

There total 8 articles about (1R,2R,5S)-2-acetamido-3-(benzo[d][1,3]dioxol-5-yl)-5-((tertbutyldimethylsilyl)oxy)cyclohex-3-en-1-yl 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: 90.0%

: 1374215-47-0
(1R,2S,5S)-2-acetamido-5-((tert-butyldimethylsilyl)oxy)-3-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-en-1-yl acetate

: 94839-07-3
3,4-(methylenedioxy)-benzeneboronic acid

: 1374215-48-1
(1R,2R,5S)-2-acetamido-3-(benzo[d][1,3]dioxol-5-yl)-5-((tertbutyldimethylsilyl)oxy)cyclohex-3-en-1-yl acetate

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; lithium hydroxide; In 1,2-dimethoxyethane; water; at 20 - 50 ℃; for 3h; Inert atmosphere;
DOI:10.1021/ol300996m

Reference yield:

: 1374215-43-6
(1R,4S,6R)-4-hydroxy-7-oxabicyclo[4.1.0]hept-2-en-2-yl trifluoromethanesulfonate

: 1374215-48-1
(1R,2R,5S)-2-acetamido-3-(benzo[d][1,3]dioxol-5-yl)-5-((tertbutyldimethylsilyl)oxy)cyclohex-3-en-1-yl acetate

Guidance literature:: Multi-step reaction with 5 steps

1: 2,6-dimethylpyridine / dichloromethane / -78 °C / Inert atmosphere

2: N,N,N′,N′-tetramethylguanidinium azide / acetonitrile / 22 h / 25 °C / Inert atmosphere

3: pyridine; dmap / Inert atmosphere

4: hydrogen / ethanol / 1 h / 760.05 Torr / Inert atmosphere

5: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; lithium hydroxide / 1,2-dimethoxyethane; water / 3 h / 20 - 50 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; sodium carbonate; N,N,N′,N′-tetramethylguanidinium azide; lithium hydroxide; In 1,2-dimethoxyethane; ethanol; dichloromethane; water; acetonitrile; 5: Suzuki coupling;
DOI:10.1021/ol300996m

Reference yield:

: 1374215-45-8
(1R,4S,6R)-4-((tert-butyldimethylsilyl)oxy)-7-oxabicyclo[4.1.0]hept-2-en-2-yl-trifluoromethanesulfonate

: 1374215-48-1
(1R,2R,5S)-2-acetamido-3-(benzo[d][1,3]dioxol-5-yl)-5-((tertbutyldimethylsilyl)oxy)cyclohex-3-en-1-yl acetate

Guidance literature:: Multi-step reaction with 4 steps

1: N,N,N′,N′-tetramethylguanidinium azide / acetonitrile / 22 h / 25 °C / Inert atmosphere

2: pyridine; dmap / Inert atmosphere

3: hydrogen / ethanol / 1 h / 760.05 Torr / Inert atmosphere

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; lithium hydroxide / 1,2-dimethoxyethane; water / 3 h / 20 - 50 °C / Inert atmosphere

With pyridine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; hydrogen; sodium carbonate; N,N,N′,N′-tetramethylguanidinium azide; lithium hydroxide; In 1,2-dimethoxyethane; ethanol; water; acetonitrile; 4: Suzuki coupling;
DOI:10.1021/ol300996m