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

Base Information

Chemical Name:(3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-(1-tert-butyldimethylsilyloxymethylethenyl)-2-azetidinone
CAS No.:143139-23-5
Molecular Formula:C₂₂H₃₃NO₅Si
Molecular Weight:419.593
Hs Code.:

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

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

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

There total 9 articles about (3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-(1-tert-butyldimethylsilyloxymethylethenyl)-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: 88.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 104362-57-4
(3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-(1-hydroxymethylethenyl)-2-azetidinone

: 143139-23-5
(3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-(1-tert-butyldimethylsilyloxymethylethenyl)-2-azetidinone

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 2h; Ambient temperature;
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

: 143139-23-5
(3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-(1-tert-butyldimethylsilyloxymethylethenyl)-2-azetidinone

Guidance literature:: Multi-step reaction with 8 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: 95 percent / Cl₂ / ethyl acetate; CCl₄ / 1 h / Ambient temperature

6: 67 percent / ceric ammonium nitrate (CAN) / acetonitrile; H₂O / 0.5 h / Ambient temperature

7: 83 percent / Cu₂O, p-toluenesulfonic acid monohydrate, water / dimethylsulfoxide / 2 h / 50 - 55 °C

8: 88 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

With pyridine; 1H-imidazole; copper(I) oxide; dmap; thionyl chloride; ammonium cerium(IV) nitrate; sulfuric acid; water; chlorine; toluene-4-sulfonic acid; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1248/cpb.40.1098

Reference yield:

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

: 143139-23-5
(3S,4S)-3-<(R)-1-benzyloxycarbonyloxyethyl>-4-(1-tert-butyldimethylsilyloxymethylethenyl)-2-azetidinone

Guidance literature:: Multi-step reaction with 6 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: 95 percent / Cl₂ / ethyl acetate; CCl₄ / 1 h / Ambient temperature

4: 67 percent / ceric ammonium nitrate (CAN) / acetonitrile; H₂O / 0.5 h / Ambient temperature

5: 83 percent / Cu₂O, p-toluenesulfonic acid monohydrate, water / dimethylsulfoxide / 2 h / 50 - 55 °C

6: 88 percent / imidazole / dimethylformamide / 2 h / Ambient temperature

With pyridine; 1H-imidazole; copper(I) oxide; dmap; thionyl chloride; ammonium cerium(IV) nitrate; water; chlorine; toluene-4-sulfonic acid; In tetrachloromethane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1248/cpb.40.1098