(5R,6R)-6-(1-Hydroxy-1-methyl-ethyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: (5R,6R)-6-(1-Hydroxy-1-methyl-ethyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester
• CAS No.: 84787-57-5
• Molecular Formula: C₁₇H₁₈N₂O₇
• Molecular Weight: 362.339
• Mol file: 84787-57-5.mol

Synonyms:(5R,6R)-6-(1-Hydroxy-1-methyl-ethyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

Chemical Property of (5R,6R)-6-(1-Hydroxy-1-methyl-ethyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6R)-6-(1-Hydroxy-1-methyl-ethyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

There total 16 articles about (5R,6R)-6-(1-Hydroxy-1-methyl-ethyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-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:

2-Diazo-4-[(2R,3R)-3-(1-hydroxy-1-methyl-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester (92620-31-0) → (5R,6R)-6-(1-Hydroxy-1-methyl-ethyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester (84787-57-5)

Guidance literature:

With dirhodium tetraacetate; In benzene; for 1h; Yield given; Heating;

DOI:10.1021/ja00344a044

Reference yield:

(S)-3-<(benzyloxycarbonyl)amino>-4-(methoxycarbonyl)butyric acid (77856-52-1) → (5R,6R)-6-(1-Hydroxy-1-methyl-ethyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester (84787-57-5)

Guidance literature:

Multi-step reaction with 13 steps

1: NaBH₄

2: Ac₂O / pyridine

3: 77 percent / LDA / tetrahydrofuran / 1 h / -78 °C

4: 88 percent Turnov_. / hydrochloric acid

5: H₂, catalyst

6: Et₃N / diethyl ether / 2 h / 25 °C

7: t-BuMgCl / diethyl ether / 12 h / 25 °C

8: 1percent AcOH / methanol / 24 h / 25 °C

9: 66 percent / CrO₃ / pyridine / 12 h / 25 °C

10: 1.) carbonyl diimidazole / 1.) THF, 25 deg C, 45 min, 2.) TFH, 25 deg C, 12 h

11: TsN₃, Et₃N / acetonitrile / 12 h / 25 °C

12: 1N HCl / methanol / 0.67 h / 25 °C

13: Rh₂(OAc)4 / benzene / 1 h / Heating

With chromium(VI) oxide; hydrogenchloride; dirhodium tetraacetate; sodium tetrahydroborate; 4-toluenesulfonyl azide; tert-butylmagnesium chloride; hydrogen; acetic anhydride; acetic acid; triethylamine; 1,1'-carbonyldiimidazole; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; diethyl ether; acetonitrile; benzene;

DOI:10.1021/ja00344a044

Reference yield:

(2R,3R)-3-Amino-5-hydroxy-2-(1-hydroxy-1-methyl-ethyl)-pentanoic acid methyl ester (84787-58-6) → (5R,6R)-6-(1-Hydroxy-1-methyl-ethyl)-3,7-dioxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester (84787-57-5)

Guidance literature:

Multi-step reaction with 8 steps

1: Et₃N / diethyl ether / 2 h / 25 °C

2: t-BuMgCl / diethyl ether / 12 h / 25 °C

3: 1percent AcOH / methanol / 24 h / 25 °C

4: 66 percent / CrO₃ / pyridine / 12 h / 25 °C

5: 1.) carbonyl diimidazole / 1.) THF, 25 deg C, 45 min, 2.) TFH, 25 deg C, 12 h

6: TsN₃, Et₃N / acetonitrile / 12 h / 25 °C

7: 1N HCl / methanol / 0.67 h / 25 °C

8: Rh₂(OAc)4 / benzene / 1 h / Heating

With chromium(VI) oxide; hydrogenchloride; dirhodium tetraacetate; 4-toluenesulfonyl azide; tert-butylmagnesium chloride; acetic acid; triethylamine; 1,1'-carbonyldiimidazole; In pyridine; methanol; diethyl ether; acetonitrile; benzene;

DOI:10.1021/ja00344a044

upstream raw materials:

2-Diazo-4-[(2R,3R)-3-(1-hydroxy-1-methyl-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester

(S)-3-<(benzyloxycarbonyl)amino>-4-(methoxycarbonyl)butyric acid

(2R,3R)-3-Amino-5-hydroxy-2-(1-hydroxy-1-methyl-ethyl)-pentanoic acid methyl ester

(3R,4R)-4-(2-Hydroxy-ethyl)-3-(1-methyl-1-trimethylsilanyloxy-ethyl)-azetidin-2-one

Downstream raw materials:

p-nitrobenzyl 5,6-cis-3-<(E)-2-acetamidovinylthio>-6-(1-hydroxy-1-methylethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

p-nitrobenzyl 5,6-cis-3-(2-acetylamidoethylthio)-6-(1-hydroxy-1-methylethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

(5R,6R)-3-(Diphenoxy-phosphoryloxy)-6-(1-hydroxy-1-methyl-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(5R,6R)-3-((S)-(E)-2-Acetylamino-ethenesulfinyl)-6-(1-hydroxy-1-methyl-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester