trans-benzyl 3-hydroxy-2-<2-oxo-3-isopropyl-4-(methylsulfonyloxymethyl)azetidin-1-yl>but-2-enoate

Base Information

Chemical Name:trans-benzyl 3-hydroxy-2-<2-oxo-3-isopropyl-4-(methylsulfonyloxymethyl)azetidin-1-yl>but-2-enoate
CAS No.:136582-28-0
Molecular Formula:C₁₉H₂₅NO₇S
Molecular Weight:411.476
Hs Code.:

Synonyms:trans-benzyl 3-hydroxy-2-<2-oxo-3-isopropyl-4-(methylsulfonyloxymethyl)azetidin-1-yl>but-2-enoate

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Chemical Property of trans-benzyl 3-hydroxy-2-<2-oxo-3-isopropyl-4-(methylsulfonyloxymethyl)azetidin-1-yl>but-2-enoate

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Technology Process of trans-benzyl 3-hydroxy-2-<2-oxo-3-isopropyl-4-(methylsulfonyloxymethyl)azetidin-1-yl>but-2-enoate

There total 24 articles about trans-benzyl 3-hydroxy-2-<2-oxo-3-isopropyl-4-(methylsulfonyloxymethyl)azetidin-1-yl>but-2-enoate 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:

: 124156-27-0
cis-1-p-anisyl-3-isopropyl-4-carbethoxy-2-azetidinone

: 136582-28-0
cis-benzyl 3-hydroxy-2-<2-oxo-3-isopropyl-4-(methylsulfonyloxymethyl)azetidin-1-yl>but-2-enoate

Guidance literature:: Multi-step reaction with 6 steps

1: 85.8 percent / aq. NaOH / tetrahydrofuran / 96 h / 40 °C

2: 1.) N,N'-carbonyldiimidazole, 2.) NaBH₄ / 1.) DMF, -10 deg C, 2.) methanol, from 0 deg C to RT

3: 89 percent / pyridine / 0 °C

4: 74 percent / ammonium cerium(IV) nitrate / H₂O; acetonitrile / -10 - 0 °C

5: CH₂Cl₂; hexane / 16 h / 70 °C

6: 1.) pyridine, thionyl chloride, 2.) Zn, aq. acetic acid / 1.) THF, -25 deg C, 1 h, 2.) from 4 deg C to 25 deg C, 2 h

With pyridine; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; ammonium cerium(IV) nitrate; acetic acid; 1,1'-carbonyldiimidazole; zinc; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile;

Reference yield:

: 124156-28-1
cis-3-isopropyl-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylic acid

: 136582-28-0
cis-benzyl 3-hydroxy-2-<2-oxo-3-isopropyl-4-(methylsulfonyloxymethyl)azetidin-1-yl>but-2-enoate

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) N,N'-carbonyldiimidazole, 2.) NaBH₄ / 1.) DMF, -10 deg C, 2.) methanol, from 0 deg C to RT

2: 89 percent / pyridine / 0 °C

3: 74 percent / ammonium cerium(IV) nitrate / H₂O; acetonitrile / -10 - 0 °C

4: CH₂Cl₂; hexane / 16 h / 70 °C

5: 1.) pyridine, thionyl chloride, 2.) Zn, aq. acetic acid / 1.) THF, -25 deg C, 1 h, 2.) from 4 deg C to 25 deg C, 2 h

With pyridine; sodium tetrahydroborate; thionyl chloride; ammonium cerium(IV) nitrate; acetic acid; 1,1'-carbonyldiimidazole; zinc; In hexane; dichloromethane; water; acetonitrile;

Reference yield:

: 124156-27-0,129374-72-7
ethyl 3-isopropyl-1-(4-methoxyphenyl)-4-oxoazetidin-2-carboxylate

: 136582-28-0
cis-benzyl 3-hydroxy-2-<2-oxo-3-isopropyl-4-(methylsulfonyloxymethyl)azetidin-1-yl>but-2-enoate

Guidance literature:: Multi-step reaction with 7 steps

1: NaBH₄ / methanol / 4 h / 0 °C

2: 85.8 percent / aq. NaOH / tetrahydrofuran / 96 h / 40 °C

3: 1.) N,N'-carbonyldiimidazole, 2.) NaBH₄ / 1.) DMF, -10 deg C, 2.) methanol, from 0 deg C to RT

4: 89 percent / pyridine / 0 °C

5: 74 percent / ammonium cerium(IV) nitrate / H₂O; acetonitrile / -10 - 0 °C

6: CH₂Cl₂; hexane / 16 h / 70 °C

7: 1.) pyridine, thionyl chloride, 2.) Zn, aq. acetic acid / 1.) THF, -25 deg C, 1 h, 2.) from 4 deg C to 25 deg C, 2 h

With pyridine; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; ammonium cerium(IV) nitrate; acetic acid; 1,1'-carbonyldiimidazole; zinc; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetonitrile;