(3S,5R,6S)-6-azido-3-((tert-butyldimethylsilyl)oxy)-5-hydroxycyclohex-1-en-1-yl trifluoromethanesulfonate

Base Information

Chemical Name:(3S,5R,6S)-6-azido-3-((tert-butyldimethylsilyl)oxy)-5-hydroxycyclohex-1-en-1-yl trifluoromethanesulfonate
CAS No.:1374215-49-2
Molecular Formula:C₁₃H₂₂F₃N₃O₅SSi
Molecular Weight:417.481
Hs Code.:

Synonyms:(3S,5R,6S)-6-azido-3-((tert-butyldimethylsilyl)oxy)-5-hydroxycyclohex-1-en-1-yl trifluoromethanesulfonate

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Chemical Property of (3S,5R,6S)-6-azido-3-((tert-butyldimethylsilyl)oxy)-5-hydroxycyclohex-1-en-1-yl trifluoromethanesulfonate

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Technology Process of (3S,5R,6S)-6-azido-3-((tert-butyldimethylsilyl)oxy)-5-hydroxycyclohex-1-en-1-yl trifluoromethanesulfonate

There total 5 articles about (3S,5R,6S)-6-azido-3-((tert-butyldimethylsilyl)oxy)-5-hydroxycyclohex-1-en-1-yl trifluoromethanesulfonate 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%

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

: 1374215-49-2
(3S,5R,6S)-6-azido-3-((tert-butyldimethylsilyl)oxy)-5-hydroxycyclohex-1-en-1-yl trifluoromethanesulfonate

Guidance literature:: With N,N,N′,N′-tetramethylguanidinium azide; In acetonitrile; at 25 ℃; for 22h; regioselective reaction; Inert atmosphere;
DOI:10.1021/ol300996m

Reference yield:

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

: 1374215-49-2
(3S,5R,6S)-6-azido-3-((tert-butyldimethylsilyl)oxy)-5-hydroxycyclohex-1-en-1-yl trifluoromethanesulfonate

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

: 1374215-42-5
(S)-3-hydroxycyclohexa-1,5-dien-1-yl trifluoromethanesulfonate

: 1374215-49-2
(3S,5R,6S)-6-azido-3-((tert-butyldimethylsilyl)oxy)-5-hydroxycyclohex-1-en-1-yl trifluoromethanesulfonate

Guidance literature:: Multi-step reaction with 3 steps

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

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

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

With 2,6-dimethylpyridine; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; N,N,N′,N′-tetramethylguanidinium azide; In dichloromethane; acetonitrile;
DOI:10.1021/ol300996m