Oxazolidine, 4-(azidomethyl)-5-[(1E)-3-hydroxy-1-propenyl]-2,2-dimethyl-3-[(4-methyl phenyl)sulfonyl]-, (4R,5R)-

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Chemical Name:Oxazolidine, 4-(azidomethyl)-5-[(1E)-3-hydroxy-1-propenyl]-2,2-dimethyl-3-[(4-methyl phenyl)sulfonyl]-, (4R,5R)-
CAS No.:881309-49-5
Molecular Formula:C16H22N4O4S
Molecular Weight:366.441
Hs Code.:

Synonyms:

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Chemical Property of Oxazolidine, 4-(azidomethyl)-5-[(1E)-3-hydroxy-1-propenyl]-2,2-dimethyl-3-[(4-methyl phenyl)sulfonyl]-, (4R,5R)-

Chemical Property:

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Technology Process of Oxazolidine, 4-(azidomethyl)-5-[(1E)-3-hydroxy-1-propenyl]-2,2-dimethyl-3-[(4-methyl phenyl)sulfonyl]-, (4R,5R)-

There total 5 articles about Oxazolidine, 4-(azidomethyl)-5-[(1E)-3-hydroxy-1-propenyl]-2,2-dimethyl-3-[(4-methyl phenyl)sulfonyl]-, (4R,5R)- 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: 70.0%

: 881309-48-4
(E)-3-[(4R,5R)-4-Azidomethyl-2,2-dimethyl-3-(toluene-4-sulfonyl)-oxazolidin-5-yl]-propenal

: 881309-49-5
(E)-3-[(4R,5R)-4-Azidomethyl-2,2-dimethyl-3-(toluene-4-sulfonyl)-oxazolidin-5-yl]-prop-2-en-1-ol

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 ℃; for 0.5h;
DOI:10.1016/j.tetlet.2005.12.123

Reference yield:

: N-((1S,2S)-3-Benzenesulfinyl-1-bromomethyl-2-hydroxy-propyl)-4-methyl-benzenesulfonamide

: 881309-49-5
(E)-3-[(4R,5R)-4-Azidomethyl-2,2-dimethyl-3-(toluene-4-sulfonyl)-oxazolidin-5-yl]-prop-2-en-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 70 percent / CSA / acetone / 6 h / 70 °C

2.1: 90 percent / NaN₃ / dimethylsulfoxide / 6 h / 80 °C

3.1: trifluoroacetic anhydride / CH₂Cl₂ / 0.5 h / 0 °C

3.2: 70 percent / SnCl₄ / 0.08 h / 0 °C

4.1: O₃ / CH₂Cl₂ / 30 h / -78 °C

4.2: 75 percent / Me₂S / 0.5 h / -78 - 0 °C

5.1: 70 percent / NaBH₄; CeCl₃ / methanol / 0.5 h / 0 °C

With sodium tetrahydroborate; sodium azide; cerium(III) chloride; ozone; trifluoroacetic anhydride; camphor-10-sulfonic acid; In methanol; dichloromethane; dimethyl sulfoxide; acetone; 5.1: Luche reduction;
DOI:10.1016/j.tetlet.2005.12.123

Reference yield:

: 881309-46-2
(4S,5S)-5-Benzenesulfinylmethyl-4-bromomethyl-2,2-dimethyl-3-(toluene-4-sulfonyl)-oxazolidine

: 881309-49-5
(E)-3-[(4R,5R)-4-Azidomethyl-2,2-dimethyl-3-(toluene-4-sulfonyl)-oxazolidin-5-yl]-prop-2-en-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 90 percent / NaN₃ / dimethylsulfoxide / 6 h / 80 °C

2.1: trifluoroacetic anhydride / CH₂Cl₂ / 0.5 h / 0 °C

2.2: 70 percent / SnCl₄ / 0.08 h / 0 °C

3.1: O₃ / CH₂Cl₂ / 30 h / -78 °C

3.2: 75 percent / Me₂S / 0.5 h / -78 - 0 °C

4.1: 70 percent / NaBH₄; CeCl₃ / methanol / 0.5 h / 0 °C

With sodium tetrahydroborate; sodium azide; cerium(III) chloride; ozone; trifluoroacetic anhydride; In methanol; dichloromethane; dimethyl sulfoxide; 4.1: Luche reduction;
DOI:10.1016/j.tetlet.2005.12.123