(4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-{(2S,3S,4R)-2-iodomethyl-4-[(4-nitro-benzyloxycarbonylamino)-methyl]-oxetan-3-ylsulfanyl}-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-{(2S,3S,4R)-2-iodomethyl-4-[(4-nitro-benzyloxycarbonylamino)-methyl]-oxetan-3-ylsulfanyl}-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
• CAS No.: 195001-00-4
• Molecular Formula: C₃₀H₃₁IN₄O₁₁S
• Molecular Weight: 782.567

Synonyms:

Chemical Property of (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-{(2S,3S,4R)-2-iodomethyl-4-[(4-nitro-benzyloxycarbonylamino)-methyl]-oxetan-3-ylsulfanyl}-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-{(2S,3S,4R)-2-iodomethyl-4-[(4-nitro-benzyloxycarbonylamino)-methyl]-oxetan-3-ylsulfanyl}-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

There total 14 articles about (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-{(2S,3S,4R)-2-iodomethyl-4-[(4-nitro-benzyloxycarbonylamino)-methyl]-oxetan-3-ylsulfanyl}-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl 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:

methyl 2,4-anhydro-3,5-di-O-benzyl-D-lyxonate (131139-12-3) → (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-{(2S,3S,4R)-2-iodomethyl-4-[(4-nitro-benzyloxycarbonylamino)-methyl]-oxetan-3-ylsulfanyl}-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (195001-00-4)

Guidance literature:

Multi-step reaction with 13 steps

1: H₂ / Pd/C

2: 84 percent / imidazole

3: pyridine

4: K₂CO₃, 18-crown-6

5: 45 percent / DIBAL / tetrahydrofuran / -20 - 0 °C

6: pyridine

7: LiN₃

8: 1.) Ph₃P, 2.) NaOH

9: 82 percent / TBAF

10: pyridine

11: TBAI

12: 92 percent / Hg(OCOCF₃)2, anisole / acetic acid; H₂O / Ambient temperature

13: i-PrNEt / acetonitrile

With pyridine; 1H-imidazole; sodium hydroxide; lithium azide; 18-crown-6 ether; i-PrNEt; tetrabutyl ammonium fluoride; hydrogen; mercury(II) trifluoroacetate; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; potassium carbonate; methoxybenzene; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; water; acetic acid; acetonitrile;

DOI:10.1016/S0960-894X(97)00280-1

Reference yield:

methyl 2,4-anhydro-D-lyxonate (134651-25-5) → (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-{(2S,3S,4R)-2-iodomethyl-4-[(4-nitro-benzyloxycarbonylamino)-methyl]-oxetan-3-ylsulfanyl}-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (195001-00-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 84 percent / imidazole

2: pyridine

3: K₂CO₃, 18-crown-6

4: 45 percent / DIBAL / tetrahydrofuran / -20 - 0 °C

5: pyridine

6: LiN₃

7: 1.) Ph₃P, 2.) NaOH

8: 82 percent / TBAF

9: pyridine

10: TBAI

11: 92 percent / Hg(OCOCF₃)2, anisole / acetic acid; H₂O / Ambient temperature

12: i-PrNEt / acetonitrile

With pyridine; 1H-imidazole; sodium hydroxide; lithium azide; 18-crown-6 ether; i-PrNEt; tetrabutyl ammonium fluoride; mercury(II) trifluoroacetate; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; potassium carbonate; methoxybenzene; triphenylphosphine; In tetrahydrofuran; water; acetic acid; acetonitrile;

DOI:10.1016/S0960-894X(97)00280-1

Reference yield:

methyl 2,4-anhydro-5-O-tertbutyldiphenylsilyl-D-lyxonate (134651-26-6) → (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-{(2S,3S,4R)-2-iodomethyl-4-[(4-nitro-benzyloxycarbonylamino)-methyl]-oxetan-3-ylsulfanyl}-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (195001-00-4)

Guidance literature:

Multi-step reaction with 11 steps

1: pyridine

2: K₂CO₃, 18-crown-6

3: 45 percent / DIBAL / tetrahydrofuran / -20 - 0 °C

4: pyridine

5: LiN₃

6: 1.) Ph₃P, 2.) NaOH

7: 82 percent / TBAF

8: pyridine

9: TBAI

10: 92 percent / Hg(OCOCF₃)2, anisole / acetic acid; H₂O / Ambient temperature

11: i-PrNEt / acetonitrile

With pyridine; sodium hydroxide; lithium azide; 18-crown-6 ether; i-PrNEt; tetrabutyl ammonium fluoride; mercury(II) trifluoroacetate; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; potassium carbonate; methoxybenzene; triphenylphosphine; In tetrahydrofuran; water; acetic acid; acetonitrile;

DOI:10.1016/S0960-894X(97)00280-1

upstream raw materials:

(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

((2R,3S,4S)-4-Iodomethyl-3-mercapto-oxetan-2-ylmethyl)-carbamic acid 4-nitro-benzyl ester

methyl 2,4-anhydro-3,5-di-O-benzyl-D-lyxonate

methyl 2,4-anhydro-D-lyxonate

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