P-NITROBENZYL (2R,5R,6S)-6-[(R)-1-HYDROXYETHYL]-3,7-DIOXO-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLATE

Base Information Edit

Chemical Name:P-NITROBENZYL (2R,5R,6S)-6-[(R)-1-HYDROXYETHYL]-3,7-DIOXO-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLATE
CAS No.:75363-99-4
Molecular Formula:C16H16N2O7
Molecular Weight:348.312
Hs Code.:
Mol file:75363-99-4.mol

Synonyms:1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLIC ACID;

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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 P-NITROBENZYL (2R,5R,6S)-6-[(R)-1-HYDROXYETHYL]-3,7-DIOXO-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLATE Edit

Chemical Property:

PSA：129.73000
LogP:0.64830

Purity/Quality:: 99% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of P-NITROBENZYL (2R,5R,6S)-6-[(R)-1-HYDROXYETHYL]-3,7-DIOXO-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLATE

There total 52 articles about P-NITROBENZYL (2R,5R,6S)-6-[(R)-1-HYDROXYETHYL]-3,7-DIOXO-1-AZABICYCLO[3.2.0]HEPTANE-2-CARBOXYLATE 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: 94.0%

: (3RS,4RS)-α-diazo-3-[1(RS)-hydroxyethyl]-β,2-dioxo-4-azetidinebutanoic acid p-nitrobenzyl ester

: 74288-40-7,75363-99-4,77171-48-3,77448-91-0,77449-43-5,78184-67-5,111468-09-8,115938-32-4
p-nitrobenzyl 6-(1'-hydroxyethyl)-1-azabicyclo(3.2.0)heptane-3,7-dione-2-carboxylate

Guidance literature:: dirhodium tetraacetate; zinc dibromide; In ethyl acetate; at 75 - 77 ℃; for 1h; Product distribution / selectivity;

Reference yield:

: (3RS,4RS)-α-diazo-3-[1(RS)-hydroxyethyl]-β,2-dioxo-4-azetidinebutanoic acid p-nitrobenzyl ester

: 74288-40-7,75363-99-4,77171-48-3,77448-91-0,77449-43-5,78184-67-5,111468-09-8,115938-32-4
(2S,5S,6R)-6-((S)-1-Hydroxy-ethyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: dirhodium tetraacetate; In toluene; at 80 ℃; for 1h;
DOI:10.1016/S0040-4039(00)78606-0

Reference yield:

: 77120-91-3
(E)-2-Acetyl-3-benzylamino-pent-2-enedioic acid diethyl ester

: 74288-40-7,75363-99-4,77171-48-3,77448-91-0,77449-43-5,78184-67-5,111468-09-8,115938-32-4
(2S,5S,6R)-6-((S)-1-Hydroxy-ethyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: NaBH₃CN / acetic acid

2: cc. HCl / Heating

3: hydrogen / Pd(OH)2/C / acetic acid / 2068.6 Torr

4: AcOH / 16 h / 70 °C

5: 92 percent / NEt₃, DCC / acetonitrile / 4 h / 60 °C

6: NEt₃ / dimethylformamide

7: hydrogen / Pd/c / 2068.6 Torr

8: 1.) carbonyldiimidazol, 4-dimethylaminopyridine / 1.) CH₂Cl₂ 2.) CH₃CN, reflux

9: HCl / methanol; H₂O

10: Triphenylphosphine, diisopropylazodicarboxylate, / THF, 25 deg C, 1 h

11: HCl / methanol; H₂O / 1.5 h / 25 °C

12: TsN₃, NEt₃ / ethyl acetate

13: Rh₂(OAc)4 / toluene / 1 h / 80 °C

With hydrogenchloride; dmap; Carbonyldiimidazole; 4-toluenesulfonyl azide; di-isopropyl azodicarboxylate; hydrogen; sodium cyanoborohydride; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; dirhodium tetraacetate; palladium dihydroxide; palladium on activated charcoal; acetic acid; In methanol; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1016/S0040-4039(00)78606-0