(3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-carboxyethyl>-2-azetidinone

Base Information

Chemical Name:(3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-carboxyethyl>-2-azetidinone
CAS No.:104362-99-4
Molecular Formula:C₁₆H₁₉NO₆
Molecular Weight:321.33
Hs Code.:

Synonyms:(3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-carboxyethyl>-2-azetidinone

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-carboxyethyl>-2-azetidinone

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Technology Process of (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-carboxyethyl>-2-azetidinone

There total 9 articles about (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-carboxyethyl>-2-azetidinone 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: 84.0%

: 104362-98-3
(3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-hydroxymethylethyl>-2-azetidinone

: 104362-99-4
(3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-carboxyethyl>-2-azetidinone

Guidance literature:: With chromium(VI) oxide; sulfuric acid; In acetone; at 10 - 20 ℃;
DOI:10.1248/cpb.40.1098

Reference yield:

: 86258-97-1
(3S,4S)-4-carboxy-1-(di-p-anisylmethyl)-3-<(R)-1-hydroxyethyl>-2-azetidinone

: 104362-99-4
(3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-carboxyethyl>-2-azetidinone

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / 98percent aq. H₂SO₄ / 3 h / 65 °C

2: 88 percent / tetrahydrofuran / 1 h / 0 - 5 °C

3: 100 percent / 4-dimethylaminopyridine (DMAP) / CH₂Cl₂ / 12 h / 0 - 20 °C

4: 89 percent / SOCl₂, pyridine / toluene / 5 h / 20 - 30 °C

5: 72 percent / ceric ammonium nitrate (CAN) / acetonitrile; H₂O / 0.5 h / Ambient temperature

6: 1.) boron trifluoride etherate, NaBH₄, 1,5-cyclooctadiene, 2.) 35percent aq. H₂O₂, aq. NaOH / 1.) THF, 3 h, 2.) THF, 40-45 deg C

7: 84 percent / CrO₃, aq. H₂SO₄ / acetone / 10 - 20 °C

With pyridine; chromium(VI) oxide; dmap; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; 1,5-cis,cis-cyclooctadiene; ammonium cerium(IV) nitrate; sulfuric acid; boron trifluoride diethyl etherate; dihydrogen peroxide; In tetrahydrofuran; dichloromethane; water; acetone; toluene; acetonitrile;
DOI:10.1248/cpb.40.1098

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 104362-99-4
(3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-<(R)-1-carboxyethyl>-2-azetidinone

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / 4-dimethylaminopyridine (DMAP) / CH₂Cl₂ / 12 h / 0 - 20 °C

2: 89 percent / SOCl₂, pyridine / toluene / 5 h / 20 - 30 °C

3: 72 percent / ceric ammonium nitrate (CAN) / acetonitrile; H₂O / 0.5 h / Ambient temperature

4: 1.) boron trifluoride etherate, NaBH₄, 1,5-cyclooctadiene, 2.) 35percent aq. H₂O₂, aq. NaOH / 1.) THF, 3 h, 2.) THF, 40-45 deg C

5: 84 percent / CrO₃, aq. H₂SO₄ / acetone / 10 - 20 °C

With pyridine; chromium(VI) oxide; dmap; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; 1,5-cis,cis-cyclooctadiene; ammonium cerium(IV) nitrate; sulfuric acid; boron trifluoride diethyl etherate; dihydrogen peroxide; In dichloromethane; water; acetone; toluene; acetonitrile;
DOI:10.1248/cpb.40.1098