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

Base Information

Chemical Name:(1R,2S,5S)-2-acetamido-5-((tert-butyldimethylsilyl)oxy)-3-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-en-1-yl acetate
CAS No.:1374215-47-0
Molecular Formula:C₁₇H₂₈F₃NO₇SSi
Molecular Weight:475.559
Hs Code.:

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

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Chemical Property of (1R,2S,5S)-2-acetamido-5-((tert-butyldimethylsilyl)oxy)-3-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-en-1-yl acetate

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Technology Process of (1R,2S,5S)-2-acetamido-5-((tert-butyldimethylsilyl)oxy)-3-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-en-1-yl acetate

There total 6 articles about (1R,2S,5S)-2-acetamido-5-((tert-butyldimethylsilyl)oxy)-3-(((trifluoromethyl)sulfonyl)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:

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

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

Guidance literature:: Multi-step reaction with 4 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

With pyridine; 2,6-dimethylpyridine; dmap; hydrogen; N,N,N′,N′-tetramethylguanidinium azide; In ethanol; dichloromethane; acetonitrile;
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

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

Guidance literature:: Multi-step reaction with 3 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

With pyridine; dmap; hydrogen; N,N,N′,N′-tetramethylguanidinium azide; In ethanol; acetonitrile;
DOI:10.1021/ol300996m

Reference yield:

: 63028-10-4
cyclohexa-2,4-dienyl trifluoromethanesulfonate

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

Guidance literature:: Multi-step reaction with 7 steps

1.1: ammonium tetrafluoroborate; sodium phosphate / methanol / 0.08 h / 0 °C / Inert atmosphere

1.2: 0.08 h / Inert atmosphere

1.3: 2 h / Inert atmosphere

2.1: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

3.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 7 h / 25 °C / Inert atmosphere

4.1: 2,6-dimethylpyridine / dichloromethane / -78 °C / Inert atmosphere

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

6.1: pyridine; dmap / Inert atmosphere

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

With pyridine; 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; ammonium tetrafluoroborate; hydrogen; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; N,N,N′,N′-tetramethylguanidinium azide; sodium phosphate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetonitrile;
DOI:10.1021/ol300996m