[(2R,3S)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-thioacetic acid S-[2-(4-nitro-benzyloxycarbonylamino)-ethyl] ester

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Chemical Name:[(2R,3S)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-thioacetic acid S-[2-(4-nitro-benzyloxycarbonylamino)-ethyl] ester
CAS No.:92133-37-4
Molecular Formula:C₁₇H₂₁N₃O₇S
Molecular Weight:411.436
Hs Code.:

Synonyms:[(2R,3S)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-thioacetic acid S-[2-(4-nitro-benzyloxycarbonylamino)-ethyl] ester

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Chemical Property of [(2R,3S)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-thioacetic acid S-[2-(4-nitro-benzyloxycarbonylamino)-ethyl] ester

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Technology Process of [(2R,3S)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-thioacetic acid S-[2-(4-nitro-benzyloxycarbonylamino)-ethyl] ester

There total 6 articles about [(2R,3S)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-thioacetic acid S-[2-(4-nitro-benzyloxycarbonylamino)-ethyl] ester 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:

: 90628-97-0
3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-4(R)-<<<<2-<<(p-nitrobenzyloxy)carbonyl>amino>ethyl>thio>carbonyl>methyl>azetidin-2-one

: 92133-37-4
[(2R,3S)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-thioacetic acid S-[2-(4-nitro-benzyloxycarbonylamino)-ethyl] ester

Guidance literature:: With boron trifluoride diethyl etherate; In acetonitrile; at 0 ℃; for 0.5h; Yield given;
DOI:10.1016/S0040-4039(01)81292-2

Reference yield:

: 76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1
(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

: 92133-37-4
[(2R,3S)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-thioacetic acid S-[2-(4-nitro-benzyloxycarbonylamino)-ethyl] ester

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / Et₃N / tetrahydrofuran / 2 h / Ambient temperature

2: trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / Ambient temperature; overnight

3: 91 percent / pyridinium p-toluenesulfonate / tetrahydrofuran; H₂O / 0.5 h / Ambient temperature

4: 100 percent / H₂ / 10percent Pd-C / methanol

5: N,N'-dicyclohexylcarbodiimide / 4-(N,N-dimethylamino)pyridine / benzene

6: boron trifluoride etherate / acetonitrile / 0.5 h / 0 °C

With boron trifluoride diethyl etherate; hydrogen; triethylamine; dicyclohexyl-carbodiimide; dmap; palladium on activated charcoal; trimethylsilyl trifluoromethanesulfonate; pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; benzene;
DOI:10.1016/S0040-4039(01)81292-2

Reference yield:

: 87392-18-5
<3S-<3α(S^*),4β>>-benzyl<3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-yl>acetate

: 92133-37-4
[(2R,3S)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-thioacetic acid S-[2-(4-nitro-benzyloxycarbonylamino)-ethyl] ester

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / H₂ / 10percent Pd-C / methanol

2: N,N'-dicyclohexylcarbodiimide / 4-(N,N-dimethylamino)pyridine / benzene

3: boron trifluoride etherate / acetonitrile / 0.5 h / 0 °C

With boron trifluoride diethyl etherate; hydrogen; dicyclohexyl-carbodiimide; dmap; palladium on activated charcoal; In methanol; acetonitrile; benzene;
DOI:10.1016/S0040-4039(01)81292-2