(-)-(1S,2R,3S,4S,5R,6S)-5-exo-azido-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-6-endo-p-toluenesulfonyl-7-azabicyclo[2.2.1]heptane

Base Information

Chemical Name:(-)-(1S,2R,3S,4S,5R,6S)-5-exo-azido-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-6-endo-p-toluenesulfonyl-7-azabicyclo[2.2.1]heptane
CAS No.:573716-83-3
Molecular Formula:C₂₁H₂₈N₄O₆S
Molecular Weight:464.543
Hs Code.:

Synonyms:(-)-(1S,2R,3S,4S,5R,6S)-5-exo-azido-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-6-endo-p-toluenesulfonyl-7-azabicyclo[2.2.1]heptane

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Chemical Property of (-)-(1S,2R,3S,4S,5R,6S)-5-exo-azido-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-6-endo-p-toluenesulfonyl-7-azabicyclo[2.2.1]heptane

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Technology Process of (-)-(1S,2R,3S,4S,5R,6S)-5-exo-azido-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-6-endo-p-toluenesulfonyl-7-azabicyclo[2.2.1]heptane

There total 9 articles about (-)-(1S,2R,3S,4S,5R,6S)-5-exo-azido-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-6-endo-p-toluenesulfonyl-7-azabicyclo[2.2.1]heptane 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:

: 205813-79-2
tert-butyl (3aR,4S,7R,7aS)-2,2-dimethyl-5-[(4-methylphenyl)sulfonyl]-3a,4,7,7a-tetrahydro-4,7-epimino-1,3-benzodioxole-8-carboxylate

: 573716-83-3
(-)-(1S,2R,3S,4S,5R,6S)-5-exo-azido-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-6-endo-p-toluenesulfonyl-7-azabicyclo[2.2.1]heptane

: 573716-87-7
(+)-(1S,2R,3S,4S,5S,6R)-5-endo-azido-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-6-exo-p-toluenesulfonyl-7-azabicyclo[2.2.1]heptane

Guidance literature:: With trimethylsilylazide; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃;
DOI:10.1021/jo0301088

Reference yield:

: 573716-76-4
(-)-(1S,2R,3S,4R,5S,6R)-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-5-endo-methanesulfonyloxy-6-endo-p-toluenesulfonyl-7-azabicyclo[2.2.1]heptane

: 573716-83-3
(-)-(1S,2R,3S,4S,5R,6S)-5-exo-azido-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-6-endo-p-toluenesulfonyl-7-azabicyclo[2.2.1]heptane

: 573716-87-7
(+)-(1S,2R,3S,4S,5S,6R)-5-endo-azido-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-6-exo-p-toluenesulfonyl-7-azabicyclo[2.2.1]heptane

Guidance literature:: With trimethylsilylazide; tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃;
DOI:10.1021/jo0301088

Reference yield:

: 227454-54-8
5-oxo-6-(toluene-4-sulfonyl)-7-aza-bicyclo[2.2.1]hept-2-ene-7-carboxylic acid tert-butyl ester

: 573716-83-3
(-)-(1S,2R,3S,4S,5R,6S)-5-exo-azido-7-tert-butoxycarbonyl-2,3-exo-isopropylidenedioxy-6-endo-p-toluenesulfonyl-7-azabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 8 steps

1: 85 percent / LiBH₄ / tetrahydrofuran / 0.25 h / -78 °C

2: 47 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / 20 °C

3: 88 percent / NaOMe / methanol; tetrahydrofuran / 4 h / 0 °C / pH 8

4: 80 percent / OsO₄; morpholine N-oxide / acetone; H₂O; CCl₄ / 2 h

5: 84 percent / p-toluenesulfonic acid monohydrate / acetone / 0.13 h / 20 °C

6: 84 percent / DMAP; pyridine / 12 h

7: 90 percent / DBU / CH₂Cl₂ / 0.25 h / 25 °C

8: trimethylsilyl azide; Bu₄NF / tetrahydrofuran / 60 °C

With pyridine; 4-morpholinyl-N-oxide; dmap; osmium(VIII) oxide; lithium borohydride; trimethylsilylazide; tetrabutyl ammonium fluoride; sodium methylate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; acetone;
DOI:10.1021/jo0301088