(3S,4R)-3-[(1'R)-1'-(benzyloxycarbonyloxy)ethyl]-4-[(1'R)-1'-(t-butyldimethylsilyloxymethyl)ethyl]azetidin-2-one

Base Information

Chemical Name:(3S,4R)-3-[(1'R)-1'-(benzyloxycarbonyloxy)ethyl]-4-[(1'R)-1'-(t-butyldimethylsilyloxymethyl)ethyl]azetidin-2-one
CAS No.:112057-69-9
Molecular Formula:C₂₂H₃₅NO₅Si
Molecular Weight:421.609
Hs Code.:

Synonyms:(3S,4R)-3-[(1'R)-1'-(benzyloxycarbonyloxy)ethyl]-4-[(1'R)-1'-(t-butyldimethylsilyloxymethyl)ethyl]azetidin-2-one

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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,4R)-3-[(1'R)-1'-(benzyloxycarbonyloxy)ethyl]-4-[(1'R)-1'-(t-butyldimethylsilyloxymethyl)ethyl]azetidin-2-one

Chemical Property:

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Technology Process of (3S,4R)-3-[(1'R)-1'-(benzyloxycarbonyloxy)ethyl]-4-[(1'R)-1'-(t-butyldimethylsilyloxymethyl)ethyl]azetidin-2-one

There total 12 articles about (3S,4R)-3-[(1'R)-1'-(benzyloxycarbonyloxy)ethyl]-4-[(1'R)-1'-(t-butyldimethylsilyloxymethyl)ethyl]azetidin-2-one 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: 95.0%

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

: 112057-69-9,116051-97-9,143170-18-7
Carbonic acid benzyl ester (R)-1-{(2R,3S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-4-oxo-azetidin-3-yl}-ethyl ester

Guidance literature:: With hydrogen; platinum(IV) oxide; In acetonitrile; at 0 - 5 ℃; for 4h;
DOI:10.1248/cpb.40.1098

Reference yield:

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

: 112057-78-0
(3S,4R)-4-<(R)-1-(t-butyldimethylsilyloxymethyl)ethyl>-3-<(R)-1-hydroxyethyl>-2-azetidinone

: 112057-69-9
(3S,4R)-3-[(1'R)-1'-(benzyloxycarbonyloxy)ethyl]-4-[(1'R)-1'-(t-butyldimethylsilyloxymethyl)ethyl]azetidin-2-one

Guidance literature:: With dmap; In dichloromethane;

Reference yield:

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

: 112057-69-9,116051-97-9,143170-18-7
Carbonic acid benzyl ester (R)-1-{(2R,3S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-4-oxo-azetidin-3-yl}-ethyl ester

Guidance literature:: Multi-step reaction with 9 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

9: 95 percent / H₂ / PtO₂ / acetonitrile / 4 h / 0 - 5 °C

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