(1S,5R)-6-Benzyloxycarbonylmethoxy-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(1S,5R)-6-Benzyloxycarbonylmethoxy-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester
CAS No.:214412-66-5
Molecular Formula:C₁₉H₂₄N₂O₆
Molecular Weight:376.409
Hs Code.:

Synonyms:(1S,5R)-6-Benzyloxycarbonylmethoxy-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester

Suppliers and Price of (1S,5R)-6-Benzyloxycarbonylmethoxy-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (1S,5R)-6-Benzyloxycarbonylmethoxy-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (1S,5R)-6-Benzyloxycarbonylmethoxy-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester

There total 12 articles about (1S,5R)-6-Benzyloxycarbonylmethoxy-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl 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: 100.0%

: 214412-65-4
(1R,5R)-6-hydroxy-7-oxo-2,6-diazabicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester

: 5437-45-6
Benzyl bromoacetate

: 214412-66-5
(1S,5R)-6-Benzyloxycarbonylmethoxy-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1021/jm9800245

Reference yield:

: 51442-80-9
5-(tetrahydro-2H-pyran-2-yloxy)-2-pentyn-1-ol

: 214412-66-5
(1S,5R)-6-Benzyloxycarbonylmethoxy-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 84 percent / LAH, NaOMe / tetrahydrofuran / 1 h / Heating

2: 70 percent / tert-butyl hydroperoxide, 3 A molecular sieve, L-(+)-diisopropyl tartrate, tetraisopropyl orthotitanate / CH₂Cl₂; 2,2,4-trimethyl-pentane / 4 h / -20 °C

3: 76 percent / RuO₂, NaIO₄ / acetonitrile; CCl₄; H₂O / 4 h / 30 °C

4: 1.) aq. KHCO₃, 2.) aq. conc. NH₄OH / 1.) MeOH, 2.) 50 deg C, 20 h

5: dioxane; H₂O / 3 h

6: 51 percent / aq. 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / tetrahydrofuran / 4 h

7: 50 percent / diisopropyl azodicarboxylate, Ph₃P / tetrahydrofuran / 2 h / Ambient temperature

8: 87 percent / p-TsOH, EtOH / 2 h / 80 °C

9: 99 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

10: 25 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / Ambient temperature

11: 87 percent / H₂ / 10percent Pd/C / ethanol

12: 100 percent / DBU / tetrahydrofuran / 1 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; ruthenium(IV) oxide; ammonium hydroxide; sodium periodate; lithium aluminium tetrahydride; ethanol; L-(+)-diisopropyl tartrate; di-isopropyl azodicarboxylate; 3 A molecular sieve; hydrogen; sodium methylate; potassium hydrogencarbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; tetrachloromethane; 2,2,4-trimethylpentane; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jm9800245

Reference yield:

: 92844-99-0
(2E)-5-<(2-tetrahydropyranyl)oxy>pent-2-en-1-ol

: 214412-66-5
(1S,5R)-6-Benzyloxycarbonylmethoxy-7-oxo-2,6-diaza-bicyclo[3.2.0]heptane-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 70 percent / tert-butyl hydroperoxide, 3 A molecular sieve, L-(+)-diisopropyl tartrate, tetraisopropyl orthotitanate / CH₂Cl₂; 2,2,4-trimethyl-pentane / 4 h / -20 °C

2: 76 percent / RuO₂, NaIO₄ / acetonitrile; CCl₄; H₂O / 4 h / 30 °C

3: 1.) aq. KHCO₃, 2.) aq. conc. NH₄OH / 1.) MeOH, 2.) 50 deg C, 20 h

4: dioxane; H₂O / 3 h

5: 51 percent / aq. 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / tetrahydrofuran / 4 h

6: 50 percent / diisopropyl azodicarboxylate, Ph₃P / tetrahydrofuran / 2 h / Ambient temperature

7: 87 percent / p-TsOH, EtOH / 2 h / 80 °C

8: 99 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

9: 25 percent / lithium bis(trimethylsilyl)amide / tetrahydrofuran / Ambient temperature

10: 87 percent / H₂ / 10percent Pd/C / ethanol

11: 100 percent / DBU / tetrahydrofuran / 1 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; ruthenium(IV) oxide; ammonium hydroxide; sodium periodate; ethanol; L-(+)-diisopropyl tartrate; di-isopropyl azodicarboxylate; 3 A molecular sieve; hydrogen; potassium hydrogencarbonate; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; tetrachloromethane; 2,2,4-trimethylpentane; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jm9800245