Thienamycin supplier | CasNO.59995-64-1

Name
Thienamycin
EINECS 203-170-6
CAS No. 59995-64-1
Article Data13
CAS DataBase
Density 1.5g/cm³
Solubility
Melting Point
Formula C11H16 N2 O4 S
Boiling Point 514°C at 760 mmHg
Molecular Weight 272.325
Flash Point 264.7°C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid, 3-[(2-aminoethyl)thio]-6-(1-hydroxyethyl)-7-oxo-, [5R-[5a,6a(R*)]]-;(+)-Thienamycin;Thienamycin;
PSA 129.16000
LogP 0.22420

Synthetic route

: 64067-13-6
p-nitrobenzyl (5R,6S)-2-<<2-<<<(p-nitrobenzyl)oxy>carbonyl>amino>ethyl>thio>-6-<(R)-1-hydroxyethyl>carbapen-2-em-3-carboxylate

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal under 2068.6 Torr;

: 3473-63-0
formamidine acetic acid

: 118334-32-0, 118395-94-1
imipenem

A: 59995-64-1
thienamycin

B: 130641-22-4
(R)-5-((1R,2R)-1-Carbamoyl-2-hydroxy-propyl)-3-(2-formimidoylamino-ethylsulfanyl)-1-formyl-4,5-dihydro-1H-pyrrole-2-carboxylic acid

Conditions

Conditions	Yield
at 20℃; Rate constant; Product distribution;

...Expand

: 118334-32-0, 118395-94-1
imipenem

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
With hydroxide at 20℃; Rate constant;

: (3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-benzyloxycarbonyl-2-oxo-3-diazopropyl] azetidin-2-one

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multistep reaction;

: 2-Diazo-4-[(2R,3S)-3-((R)-1-formyloxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-phenyl ester

: 540-63-6
ethane-1,2-dithiol

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane; isopropyl alcohol at 25℃; for 96h;

: 75363-99-4
4-nitrobenzyl (2R,5R,6S)-6-[(1R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: DMAP, i-Pr2NEt / acetonitrile / 0 °C 2: 70 percent / i-Pr2NEt / acetonitrile / -5 °C 3: H2 / Pd/C / 2068.6 Torr View Scheme

: 75321-07-2
(3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-(4-nitrobenzyl)-oxycarbonyl-2-oxopropyl]azetidin-2-one

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 90 percent / p-carboxybenzenesulfonyl azide, Et3N / acetonitrile / 0 - 20 °C 2: rhodium(II) acetate / benzene / 80 °C 3: DMAP, i-Pr2NEt / acetonitrile / 0 °C 4: 70 percent / i-Pr2NEt / acetonitrile / -5 °C 5: H2 / Pd/C / 2068.6 Torr View Scheme

: 74288-39-4
(3S,4R)-3-[(R)-1-hydroxyethyl)-4-[3-(4-nitrobenzyl)oxycarbonyl-2-oxo-3-diazopropyl]azetidin-2-one

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: rhodium(II) acetate / benzene / 80 °C 2: DMAP, i-Pr2NEt / acetonitrile / 0 °C 3: 70 percent / i-Pr2NEt / acetonitrile / -5 °C 4: H2 / Pd/C / 2068.6 Torr View Scheme

: 75321-05-0
(3S,4R)-1-(tert-Butyldimethylsilyl)-3-<(1R)-1-hydroxyethyl>-4-(carboxymethyl)azetidin-2-one

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: tetrahydrofuran / Ambient temperature 2: 86 percent / tetrahydrofuran / Ambient temperature 3: HCl / methanol 4: 90 percent / p-carboxybenzenesulfonyl azide, Et3N / acetonitrile / 0 - 20 °C 5: rhodium(II) acetate / benzene / 80 °C 6: DMAP, i-Pr2NEt / acetonitrile / 0 °C 7: 70 percent / i-Pr2NEt / acetonitrile / -5 °C 8: H2 / Pd/C / 2068.6 Torr View Scheme

: 75321-01-6
(S)-1-(tert-Butyl-dimethyl-silanyl)-4-(2-trimethylsilanyl-[1,3]dithian-2-ylmethyl)-azetidin-2-one

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1: 82 percent Turnov. / LDA / tetrahydrofuran / -78 °C 2: K-Selectride, KI / diethyl ether / 25 °C 3: 93 percent / HgCl2, HgO / methanol; H2O / Heating 4: 76 percent / hydrogen peroxide / methanol; H2O 5: tetrahydrofuran / Ambient temperature 6: 86 percent / tetrahydrofuran / Ambient temperature 7: HCl / methanol 8: 90 percent / p-carboxybenzenesulfonyl azide, Et3N / acetonitrile / 0 - 20 °C 9: rhodium(II) acetate / benzene / 80 °C 10: DMAP, i-Pr2NEt / acetonitrile / 0 °C 11: 70 percent / i-Pr2NEt / acetonitrile / -5 °C 12: H2 / Pd/C / 2068.6 Torr View Scheme
Multi-step reaction with 11 steps 1: LDA / tetrahydrofuran / -78 °C 2: 93 percent / HgCl2, HgO / methanol; H2O / Heating 3: 76 percent / hydrogen peroxide / methanol; H2O 4: tetrahydrofuran / Ambient temperature 5: 86 percent / tetrahydrofuran / Ambient temperature 6: HCl / methanol 7: 90 percent / p-carboxybenzenesulfonyl azide, Et3N / acetonitrile / 0 - 20 °C 8: rhodium(II) acetate / benzene / 80 °C 9: DMAP, i-Pr2NEt / acetonitrile / 0 °C 10: 70 percent / i-Pr2NEt / acetonitrile / -5 °C 11: H2 / Pd/C / 2068.6 Torr View Scheme

Yield

Multi-step reaction with 12 steps
1: 82 percent Turnov. / LDA / tetrahydrofuran / -78 °C
2: K-Selectride, KI / diethyl ether / 25 °C
3: 93 percent / HgCl2, HgO / methanol; H2O / Heating
4: 76 percent / hydrogen peroxide / methanol; H2O
5: tetrahydrofuran / Ambient temperature
6: 86 percent / tetrahydrofuran / Ambient temperature
7: HCl / methanol
8: 90 percent / p-carboxybenzenesulfonyl azide, Et3N / acetonitrile / 0 - 20 °C
9: rhodium(II) acetate / benzene / 80 °C
10: DMAP, i-Pr2NEt / acetonitrile / 0 °C
11: 70 percent / i-Pr2NEt / acetonitrile / -5 °C
12: H2 / Pd/C / 2068.6 Torr
View Scheme

Multi-step reaction with 11 steps
1: LDA / tetrahydrofuran / -78 °C
2: 93 percent / HgCl2, HgO / methanol; H2O / Heating
3: 76 percent / hydrogen peroxide / methanol; H2O
4: tetrahydrofuran / Ambient temperature
5: 86 percent / tetrahydrofuran / Ambient temperature
6: HCl / methanol
7: 90 percent / p-carboxybenzenesulfonyl azide, Et3N / acetonitrile / 0 - 20 °C
8: rhodium(II) acetate / benzene / 80 °C
9: DMAP, i-Pr2NEt / acetonitrile / 0 °C
10: 70 percent / i-Pr2NEt / acetonitrile / -5 °C
11: H2 / Pd/C / 2068.6 Torr
View Scheme

: 75321-04-9
(3S,4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-(2-oxo-2-trimethylsilylethyl)-azetidin-2-one

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 76 percent / hydrogen peroxide / methanol; H2O 2: tetrahydrofuran / Ambient temperature 3: 86 percent / tetrahydrofuran / Ambient temperature 4: HCl / methanol 5: 90 percent / p-carboxybenzenesulfonyl azide, Et3N / acetonitrile / 0 - 20 °C 6: rhodium(II) acetate / benzene / 80 °C 7: DMAP, i-Pr2NEt / acetonitrile / 0 °C 8: 70 percent / i-Pr2NEt / acetonitrile / -5 °C 9: H2 / Pd/C / 2068.6 Torr View Scheme

Yield

Multi-step reaction with 9 steps
1: 76 percent / hydrogen peroxide / methanol; H2O
2: tetrahydrofuran / Ambient temperature
3: 86 percent / tetrahydrofuran / Ambient temperature
4: HCl / methanol
5: 90 percent / p-carboxybenzenesulfonyl azide, Et3N / acetonitrile / 0 - 20 °C
6: rhodium(II) acetate / benzene / 80 °C
7: DMAP, i-Pr2NEt / acetonitrile / 0 °C
8: 70 percent / i-Pr2NEt / acetonitrile / -5 °C
9: H2 / Pd/C / 2068.6 Torr
View Scheme

: 75333-88-9
(3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-((R)-1-hydroxy-ethyl)-4-(2-imidazol-1-yl-2-oxo-ethyl)-azetidin-2-one

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 86 percent / tetrahydrofuran / Ambient temperature 2: HCl / methanol 3: 90 percent / p-carboxybenzenesulfonyl azide, Et3N / acetonitrile / 0 - 20 °C 4: rhodium(II) acetate / benzene / 80 °C 5: DMAP, i-Pr2NEt / acetonitrile / 0 °C 6: 70 percent / i-Pr2NEt / acetonitrile / -5 °C 7: H2 / Pd/C / 2068.6 Torr View Scheme

: 77551-48-5
(3S,4R)-3-Acetyl-1-(tert-butyl-dimethyl-silanyl)-4-(2-trimethylsilanyl-[1,3]dithian-2-ylmethyl)-azetidin-2-one

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 11 steps 1: K-Selectride, KI / diethyl ether / 25 °C 2: 93 percent / HgCl2, HgO / methanol; H2O / Heating 3: 76 percent / hydrogen peroxide / methanol; H2O 4: tetrahydrofuran / Ambient temperature 5: 86 percent / tetrahydrofuran / Ambient temperature 6: HCl / methanol 7: 90 percent / p-carboxybenzenesulfonyl azide, Et3N / acetonitrile / 0 - 20 °C 8: rhodium(II) acetate / benzene / 80 °C 9: DMAP, i-Pr2NEt / acetonitrile / 0 °C 10: 70 percent / i-Pr2NEt / acetonitrile / -5 °C 11: H2 / Pd/C / 2068.6 Torr View Scheme

Yield

Multi-step reaction with 11 steps
1: K-Selectride, KI / diethyl ether / 25 °C
2: 93 percent / HgCl2, HgO / methanol; H2O / Heating
3: 76 percent / hydrogen peroxide / methanol; H2O
4: tetrahydrofuran / Ambient temperature
5: 86 percent / tetrahydrofuran / Ambient temperature
6: HCl / methanol
7: 90 percent / p-carboxybenzenesulfonyl azide, Et3N / acetonitrile / 0 - 20 °C
8: rhodium(II) acetate / benzene / 80 °C
9: DMAP, i-Pr2NEt / acetonitrile / 0 °C
10: 70 percent / i-Pr2NEt / acetonitrile / -5 °C
11: H2 / Pd/C / 2068.6 Torr
View Scheme

: 75321-06-1
(3S,4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-(3-p-nitrobenzyloxycarbonyl-2-oxopropyl)-azetidin-2-one

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: HCl / methanol 2: 90 percent / p-carboxybenzenesulfonyl azide, Et3N / acetonitrile / 0 - 20 °C 3: rhodium(II) acetate / benzene / 80 °C 4: DMAP, i-Pr2NEt / acetonitrile / 0 °C 5: 70 percent / i-Pr2NEt / acetonitrile / -5 °C 6: H2 / Pd/C / 2068.6 Torr View Scheme

: 75321-08-3
p-nitrobenzyl (5R,6S)-2-diphenoxy phosphoryloxy-6-[(R)-1-hydroxyethyl]-1-carbapen-2-em-3-carboxylate

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / i-Pr2NEt / acetonitrile / -5 °C 2: H2 / Pd/C / 2068.6 Torr View Scheme

: 75321-02-7, 75363-98-3, 75364-00-0, 80735-71-3
(3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-(1-hydroxy-ethyl)-4-(2-trimethylsilanyl-[1,3]dithian-2-ylmethyl)-azetidin-2-one

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 12 steps 1: 88 percent / TFAA, Me2SO, Et3N / CH2Cl2 / -78 °C 2: K-Selectride, KI / diethyl ether / 25 °C 3: 93 percent / HgCl2, HgO / methanol; H2O / Heating 4: 76 percent / hydrogen peroxide / methanol; H2O 5: tetrahydrofuran / Ambient temperature 6: 86 percent / tetrahydrofuran / Ambient temperature 7: HCl / methanol 8: 90 percent / p-carboxybenzenesulfonyl azide, Et3N / acetonitrile / 0 - 20 °C 9: rhodium(II) acetate / benzene / 80 °C 10: DMAP, i-Pr2NEt / acetonitrile / 0 °C 11: 70 percent / i-Pr2NEt / acetonitrile / -5 °C 12: H2 / Pd/C / 2068.6 Torr View Scheme

Yield

Multi-step reaction with 12 steps
1: 88 percent / TFAA, Me2SO, Et3N / CH2Cl2 / -78 °C
2: K-Selectride, KI / diethyl ether / 25 °C
3: 93 percent / HgCl2, HgO / methanol; H2O / Heating
4: 76 percent / hydrogen peroxide / methanol; H2O
5: tetrahydrofuran / Ambient temperature
6: 86 percent / tetrahydrofuran / Ambient temperature
7: HCl / methanol
8: 90 percent / p-carboxybenzenesulfonyl azide, Et3N / acetonitrile / 0 - 20 °C
9: rhodium(II) acetate / benzene / 80 °C
10: DMAP, i-Pr2NEt / acetonitrile / 0 °C
11: 70 percent / i-Pr2NEt / acetonitrile / -5 °C
12: H2 / Pd/C / 2068.6 Torr
View Scheme

: 75321-02-7
(3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-((R)-1-hydroxy-ethyl)-4-(2-trimethylsilanyl-[1,3]dithian-2-ylmethyl)-azetidin-2-one

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 93 percent / HgCl2, HgO / methanol; H2O / Heating 2: 76 percent / hydrogen peroxide / methanol; H2O 3: tetrahydrofuran / Ambient temperature 4: 86 percent / tetrahydrofuran / Ambient temperature 5: HCl / methanol 6: 90 percent / p-carboxybenzenesulfonyl azide, Et3N / acetonitrile / 0 - 20 °C 7: rhodium(II) acetate / benzene / 80 °C 8: DMAP, i-Pr2NEt / acetonitrile / 0 °C 9: 70 percent / i-Pr2NEt / acetonitrile / -5 °C 10: H2 / Pd/C / 2068.6 Torr View Scheme

Yield

Multi-step reaction with 10 steps
1: 93 percent / HgCl2, HgO / methanol; H2O / Heating
2: 76 percent / hydrogen peroxide / methanol; H2O
3: tetrahydrofuran / Ambient temperature
4: 86 percent / tetrahydrofuran / Ambient temperature
5: HCl / methanol
6: 90 percent / p-carboxybenzenesulfonyl azide, Et3N / acetonitrile / 0 - 20 °C
7: rhodium(II) acetate / benzene / 80 °C
8: DMAP, i-Pr2NEt / acetonitrile / 0 °C
9: 70 percent / i-Pr2NEt / acetonitrile / -5 °C
10: H2 / Pd/C / 2068.6 Torr
View Scheme

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

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 95 percent / Ph3P, HCOOH, EtO2CNNCO2Et / Mitsunobu's method 2: p-toluenesulfonic acid / CH2Cl2; propan-2-ol / 96 h / 25 °C View Scheme

: 4-{(2R,3S)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-diazo-3-oxo-butyric acid 4-nitro-phenyl ester

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: HCl / methanol; H2O 2: 95 percent / Ph3P, HCOOH, EtO2CNNCO2Et / Mitsunobu's method 3: p-toluenesulfonic acid / CH2Cl2; propan-2-ol / 96 h / 25 °C View Scheme

: 78963-60-7
(3R,4R)-4-acetoxy-3-<(S)-1-(tert-butyldimethylsilyloxy)ethyl>-2-azetidinone

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 83 percent / ZnCl2 / CH2Cl2 2: HCl / methanol; H2O 3: 95 percent / Ph3P, HCOOH, EtO2CNNCO2Et / Mitsunobu's method 4: p-toluenesulfonic acid / CH2Cl2; propan-2-ol / 96 h / 25 °C View Scheme

: 102046-01-5
(2S,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidine-2-carbaldehyde

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 86 percent / Jones reagent 2: 81 percent / acetic acid 3: 83 percent / ZnCl2 / CH2Cl2 4: HCl / methanol; H2O 5: 95 percent / Ph3P, HCOOH, EtO2CNNCO2Et / Mitsunobu's method 6: p-toluenesulfonic acid / CH2Cl2; propan-2-ol / 96 h / 25 °C View Scheme

: 102129-89-5
(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidine-2-carbaldehyde

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 96 percent / Jones reagent 2: 80 percent / acetic acid 3: 83 percent / ZnCl2 / CH2Cl2 4: HCl / methanol; H2O 5: 95 percent / Ph3P, HCOOH, EtO2CNNCO2Et / Mitsunobu's method 6: p-toluenesulfonic acid / CH2Cl2; propan-2-ol / 96 h / 25 °C View Scheme

: 102129-88-4
(2S,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidine-2-carboxylic acid

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 81 percent / acetic acid 2: 83 percent / ZnCl2 / CH2Cl2 3: HCl / methanol; H2O 4: 95 percent / Ph3P, HCOOH, EtO2CNNCO2Et / Mitsunobu's method 5: p-toluenesulfonic acid / CH2Cl2; propan-2-ol / 96 h / 25 °C View Scheme

: 102129-90-8
(2R,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidine-2-carboxylic acid

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 80 percent / acetic acid 2: 83 percent / ZnCl2 / CH2Cl2 3: HCl / methanol; H2O 4: 95 percent / Ph3P, HCOOH, EtO2CNNCO2Et / Mitsunobu's method 5: p-toluenesulfonic acid / CH2Cl2; propan-2-ol / 96 h / 25 °C View Scheme

: 101977-77-9
<3S,4S(E)>-3-<1(S)-hydroxyethyl>-1-(4-methoxyphenyl)-4-(2-phenylethenyl)-2-azetidinone

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: 88 percent / silylation 2: 1.) cerric ammonium nitrate / 2.) silylation 3: 91 percent / 1.) O3; 2.) Me2S / CH2Cl2 / -78 °C 4: 96 percent / Jones reagent 5: 80 percent / acetic acid 6: 83 percent / ZnCl2 / CH2Cl2 7: HCl / methanol; H2O 8: 95 percent / Ph3P, HCOOH, EtO2CNNCO2Et / Mitsunobu's method 9: p-toluenesulfonic acid / CH2Cl2; propan-2-ol / 96 h / 25 °C View Scheme

Yield

Multi-step reaction with 9 steps
1: 88 percent / silylation
2: 1.) cerric ammonium nitrate / 2.) silylation
3: 91 percent / 1.) O3; 2.) Me2S / CH2Cl2 / -78 °C
4: 96 percent / Jones reagent
5: 80 percent / acetic acid
6: 83 percent / ZnCl2 / CH2Cl2
7: HCl / methanol; H2O
8: 95 percent / Ph3P, HCOOH, EtO2CNNCO2Et / Mitsunobu's method
9: p-toluenesulfonic acid / CH2Cl2; propan-2-ol / 96 h / 25 °C
View Scheme

: 101977-83-7
(1'S,3S,4S)-3-(1'-<(tert-butyldimethylsilyl)oxy>ethyl)-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: 1.) cerric ammonium nitrate / 2.) silylation 2: 91 percent / 1.) O3; 2.) Me2S / CH2Cl2 / -78 °C 3: 96 percent / Jones reagent 4: 80 percent / acetic acid 5: 83 percent / ZnCl2 / CH2Cl2 6: HCl / methanol; H2O 7: 95 percent / Ph3P, HCOOH, EtO2CNNCO2Et / Mitsunobu's method 8: p-toluenesulfonic acid / CH2Cl2; propan-2-ol / 96 h / 25 °C View Scheme

: 102045-99-8
(3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-((E)-styryl)-azetidin-2-one

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 85 percent / 1.) O3; 2.) Me2S / CH2Cl2 / -78 °C 2: 86 percent / Jones reagent 3: 81 percent / acetic acid 4: 83 percent / ZnCl2 / CH2Cl2 5: HCl / methanol; H2O 6: 95 percent / Ph3P, HCOOH, EtO2CNNCO2Et / Mitsunobu's method 7: p-toluenesulfonic acid / CH2Cl2; propan-2-ol / 96 h / 25 °C View Scheme

: 102046-00-4
(3S,4S)-1-(tert-Butyl-dimethyl-silanyl)-3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-((E)-styryl)-azetidin-2-one

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 91 percent / 1.) O3; 2.) Me2S / CH2Cl2 / -78 °C 2: 96 percent / Jones reagent 3: 80 percent / acetic acid 4: 83 percent / ZnCl2 / CH2Cl2 5: HCl / methanol; H2O 6: 95 percent / Ph3P, HCOOH, EtO2CNNCO2Et / Mitsunobu's method 7: p-toluenesulfonic acid / CH2Cl2; propan-2-ol / 96 h / 25 °C View Scheme

: 87037-95-4, 103365-27-1, 119720-15-9, 122673-16-9, 122673-17-0, 82938-53-2
(3R,4R)-4-acetoxy-3-[(1R)-1-hydroxyethyl]azetidin-2-one

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / ZnI2 View Scheme

: 82938-52-1
(2S,3S)-3-Acetyl-1-(tert-butyl-dimethyl-silanyl)-4-oxo-azetidine-2-carboxylic acid

: 59995-64-1
thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 70 percent / Diisopropylamine*borane, magnesium trifluoroacetate 2: 82 percent / dimethylformamide; acetic acid / 70 °C 3: 81 percent / ZnI2 View Scheme

: 59995-64-1
thienamycin

: 4457-32-3
4-nitrobenzyl chloroformate

: 64066-86-0
N-<<(p-nitrobenzyl)oxy>carbonyl>thienamycin lithium salt

Conditions

Conditions	Yield
With lithium hydroxide; sodium hydrogencarbonate 1.) H2O, dioxane, ice/NaCl bath; 2.) ethyl acetate, 0.05 M LiOH; Yield given. Multistep reaction;
With lithium hydroxide; sodium hydrogencarbonate 1.) H2O, dioxane, 10 min, 2.) EtOAc; Yield given. Multistep reaction;

: 59995-64-1
thienamycin

: 64067-13-6
p-nitrobenzyl (5R,6S)-2-<<2-<<<(p-nitrobenzyl)oxy>carbonyl>amino>ethyl>thio>-6-<(R)-1-hydroxyethyl>carbapen-2-em-3-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) NaHCO3, 2.) LiOH / 1.) H2O, dioxane, 10 min, 2.) EtOAc 2: HMPA / 2.5 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 1.) NaHCO3, 2.) LiOH / 1.) H2O, dioxane, ice/NaCl bath; 2.) ethyl acetate, 0.05 M LiOH 2: 46 percent / hexamethylphosphoric acid triamide / 3 h / Ambient temperature View Scheme

: 59995-64-1
thienamycin

: 72778-08-6
p-nitrobenzyl (3S,5S,6S)-2-<<2-<<<(p-nitrobenzyl)oxy>carbonyl>amino>ethyl>thio>-6-<(R)-1-hydroxyethyl>carbapen-1-em-3-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) NaHCO3, 2.) LiOH / 1.) H2O, dioxane, 10 min, 2.) EtOAc 2: HMPA / 2.5 h / Ambient temperature 3: 24 percent / 1,5-diazabicyclo<5.4.0>ondec-5-ene / dimethylsulfoxide / 0.17 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 1.) NaHCO3, 2.) LiOH / 1.) H2O, dioxane, ice/NaCl bath; 2.) ethyl acetate, 0.05 M LiOH 2: 46 percent / hexamethylphosphoric acid triamide / 3 h / Ambient temperature 3: 21 percent / DBU / dimethylsulfoxide / 0.5 h View Scheme

: 59995-64-1
thienamycin

: 77171-32-5
Δ1-thienamycin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) NaHCO3, 2.) LiOH / 1.) H2O, dioxane, 10 min, 2.) EtOAc 2: HMPA / 2.5 h / Ambient temperature 3: 24 percent / 1,5-diazabicyclo<5.4.0>ondec-5-ene / dimethylsulfoxide / 0.17 h / Ambient temperature 4: 63 percent / H2 / 10percent Pd/c / tetrahydrofuran; ethanol / 0.5 h / Ambient temperature; phosphate buffer pH 7 View Scheme

: 59995-64-1
thienamycin

: 3-Hydroxy-5-[(1S,2R)-2-hydroxy-1-(morpholine-4-carbonyl)-propyl]-1H-pyrrole-2-carboxylic acid 4-nitro-benzyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) NaHCO3, 2.) LiOH / 1.) H2O, dioxane, 10 min, 2.) EtOAc 2: HMPA / 2.5 h / Ambient temperature 3: 2.1 mg / tetrahydrofuran / 96 h / Ambient temperature View Scheme

: 59995-64-1
thienamycin

: 72843-08-4
(2S,5S,6S)-3-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2-carboxylic acid 4-nitro-benzyl ester

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) NaHCO3, 2.) LiOH / 1.) H2O, dioxane, ice/NaCl bath; 2.) ethyl acetate, 0.05 M LiOH 2: 46 percent / hexamethylphosphoric acid triamide / 3 h / Ambient temperature 3: 21 percent / DBU / dimethylsulfoxide / 0.5 h 4: 49 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 2.5 h / Ambient temperature View Scheme

: 59995-64-1
thienamycin

: 72778-09-7
N-<<(p-nitrobenzyl)oxy>carbonyl>-O-<<(p-nitrobenzyl)oxy>carbonyl>thienamycin p-nitrobenzyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) NaHCO3, 2.) LiOH / 1.) H2O, dioxane, ice/NaCl bath; 2.) ethyl acetate, 0.05 M LiOH 2: 46 percent / hexamethylphosphoric acid triamide / 3 h / Ambient temperature 3: 58 percent / 4-(dimethylamino)pyridine / CH2Cl2 / 2.5 h / Ambient temperature View Scheme

Thienamycin Specification

The Thienamycin,with the CAS registry number 59995-64-1.It belongs to the product categories of antibiotics.This chemical's molecular formula is C₁₁H₁₆N₂O₄S and molecular weight is 272.32.

Physical properties about thienamycin are:
(1)ACD/LogP: -3.067; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -5.58; (4)ACD/LogD (pH 7.4): -5.57; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 6; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 7; (12)Index of Refraction: 1.663; (13)Molar Refractivity: 67.101 cm³; (14)Molar Volume: 181.199 cm³; (15)Surface Tension: 77.9690017700195 dyne/cm; (16)Density: 1.503 g/cm³; (17)Flash Point: 264.685 °C; (18)Enthalpy of Vaporization: 90.425 kJ/mol; (19)Boiling Point: 514.045 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:O=C(O)/C1=C(\SCCN)C[C@H]2N1C(=O)[C@@H]2[C@H](O)C;
(2)InChI:InChI=1S/C11H16N2O4S/c1-5(14)8-6-4-7(18-3-2-12)9(11(16)17)13(6)10(8)15/h5-6,8,14H,2-4,12H2,1H3,(H,16,17)/t5-,6-,8-/m1/s1;
(3)InChIKey:WKDDRNSBRWANNC-ATRFCDNQSA-N.

The toxicity data of Thienamycin as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD	intravenous	> 500mg/kg (500mg/kg)		United States Patent Document. Vol. #4006060,
mouse	LD50	parenteral	1160ug/kg (1.16mg/kg)		Journal of Antibiotics. Vol. 45, Pg. 1983, 1992.

Product Name

Thienamycin

Synthetic route

Thienamycin Specification

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