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Factory Price API 99% Thienamycin 59995-64-1 GMP Manufacturer
Cas No: 59995-64-1
USD $ 0.1-0.1 / Gram 1 Gram 100 Metric Ton/Year Xi'an Xszo Chem Co., Ltd. Contact Supplier
59995-64-1 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid, 3-[(2-aminoethyl)thio]-6-[(1R)-1-hydroxyethyl]-7-oxo-, (5R,6S)-
Cas No: 59995-64-1
USD $ 40.0-50.0 / Gram 1 Gram 1000 Metric Ton/Day WUHAN MULEI NEW MATERIAL CO., LTD Contact Supplier
Thienamycin
Cas No: 59995-64-1
No Data No Data No Data Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid, 3-[(2-aminoethyl)thio]-6-[(1R)-1-hydroxyethyl]-7-oxo-, (5R,6S)- 59995-64-1
Cas No: 59995-64-1
No Data 1 Kilogram 10000 Metric Ton/Month Shanghai Upbio Tech Co.,Ltd Contact Supplier
1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid, 3-[(2-aminoethyl)thio]-6-[(1R)-1-hydroxyethyl]-7-oxo-, (5R,6S)-
Cas No: 59995-64-1
No Data No Data 10000 Metric Ton/Month Henan Wentao Chemical Product Co., Ltd. Contact Supplier
1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid, 3-[(2-aminoethyl)thio]-6-[(1R)-1-hydroxyethyl]-7-oxo-, (5R,6S)-
Cas No: 59995-64-1
No Data 1 Kilogram 1 Metric Ton/Day Shandong Hanjiang Chemical Co., Ltd. Contact Supplier
1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid, 3-[(2-aminoethyl)thio]-6-[(1R)-1-hydroxyethyl]-7-oxo-, (5R,6S)- 59995-64-1
Cas No: 59995-64-1
USD $ 100.0-150.0 / Kilogram 1 Kilogram 1000 Metric Ton/Day Wuhan Monad Medicine Tech Co.,LTD Contact Supplier
THIENAMYCIN
Cas No: 59995-64-1
No Data 1 Gram Metric Ton/Day Afine Chemicals Limited Contact Supplier
1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid, 3-[(2-aminoethyl)thio]-6-[(1R)-1-hydroxyethyl]-7-oxo-, (5R,6S)-
Cas No: 59995-64-1
No Data No Data 5 Hangzhou J&H Chemical Co., Ltd. Contact Supplier
Thienamycin
Cas No: 59995-64-1
USD $ 100.0-100.0 / Kilogram 1 Kilogram 10000 Kilogram/Day Metric Ton/Day Zibo Hangyu Import&Export Co., Ltd Contact Supplier

59995-64-1 Usage

InChI:InChI=1/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

59995-64-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name Thienamycin

1.2 Other means of identification

Product number -
Other names (+)-thienamycin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:59995-64-1 SDS

59995-64-1Synthetic route

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

thienamycin
59995-64-1

thienamycin

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal under 2068.6 Torr;
formamidine acetic acid
3473-63-0

formamidine acetic acid

A

thienamycin
59995-64-1

thienamycin

B

(R)-5-((1R,2R)-1-Carbamoyl-2-hydroxy-propyl)-3-(2-formimidoylamino-ethylsulfanyl)-1-formyl-4,5-dihydro-1H-pyrrole-2-carboxylic acid
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
ConditionsYield
at 20℃; Rate constant; Product distribution;
Conditions
ConditionsYield
With hydroxide at 20℃; Rate constant;
(3S,4R)-3-[(R)-1-hydroxyethyl]-4-[3-benzyloxycarbonyl-2-oxo-3-diazopropyl] azetidin-2-one

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

thienamycin
59995-64-1

thienamycin

Conditions
ConditionsYield
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

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

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

ethane-1,2-dithiol

thienamycin
59995-64-1

thienamycin

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane; isopropyl alcohol at 25℃; for 96h;
4-nitrobenzyl (2R,5R,6S)-6-[(1R)-1-hydroxyethyl]-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate
75363-99-4

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

thienamycin
59995-64-1

thienamycin

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

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

thienamycin
59995-64-1

thienamycin

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

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

thienamycin
59995-64-1

thienamycin

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

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

thienamycin
59995-64-1

thienamycin

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

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

thienamycin
59995-64-1

thienamycin

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

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

thienamycin
59995-64-1

thienamycin

Conditions
ConditionsYield
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
(3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-((R)-1-hydroxy-ethyl)-4-(2-imidazol-1-yl-2-oxo-ethyl)-azetidin-2-one
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

thienamycin
59995-64-1

thienamycin

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

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

thienamycin
59995-64-1

thienamycin

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

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

thienamycin
59995-64-1

thienamycin

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

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

thienamycin
59995-64-1

thienamycin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / i-Pr2NEt / acetonitrile / -5 °C
2: H2 / Pd/C / 2068.6 Torr
View Scheme
(3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-(1-hydroxy-ethyl)-4-(2-trimethylsilanyl-[1,3]dithian-2-ylmethyl)-azetidin-2-one
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

thienamycin
59995-64-1

thienamycin

Conditions
ConditionsYield
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
(3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-((R)-1-hydroxy-ethyl)-4-(2-trimethylsilanyl-[1,3]dithian-2-ylmethyl)-azetidin-2-one
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

thienamycin
59995-64-1

thienamycin

Conditions
ConditionsYield
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

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

thienamycin
59995-64-1

thienamycin

Conditions
ConditionsYield
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

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

thienamycin
59995-64-1

thienamycin

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

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

thienamycin
59995-64-1

thienamycin

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

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

thienamycin
59995-64-1

thienamycin

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

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

thienamycin
59995-64-1

thienamycin

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

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

thienamycin
59995-64-1

thienamycin

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

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

thienamycin
59995-64-1

thienamycin

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

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

thienamycin
59995-64-1

thienamycin

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

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

thienamycin
59995-64-1

thienamycin

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

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

thienamycin
59995-64-1

thienamycin

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

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

thienamycin
59995-64-1

thienamycin

Conditions
ConditionsYield
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
(3R,4R)-4-acetoxy-3-[(1R)-1-hydroxyethyl]azetidin-2-one
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

thienamycin
59995-64-1

thienamycin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 81 percent / ZnI2
View Scheme
(2S,3S)-3-Acetyl-1-(tert-butyl-dimethyl-silanyl)-4-oxo-azetidine-2-carboxylic acid
82938-52-1

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

thienamycin
59995-64-1

thienamycin

Conditions
ConditionsYield
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
thienamycin
59995-64-1

thienamycin

4-nitrobenzyl chloroformate
4457-32-3

4-nitrobenzyl chloroformate

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

N-<<(p-nitrobenzyl)oxy>carbonyl>thienamycin lithium salt

Conditions
ConditionsYield
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;
thienamycin
59995-64-1

thienamycin

p-nitrobenzyl (5R,6S)-2-<<2-<<<(p-nitrobenzyl)oxy>carbonyl>amino>ethyl>thio>-6-<(R)-1-hydroxyethyl>carbapen-2-em-3-carboxylate
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
ConditionsYield
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
thienamycin
59995-64-1

thienamycin

p-nitrobenzyl (3S,5S,6S)-2-<<2-<<<(p-nitrobenzyl)oxy>carbonyl>amino>ethyl>thio>-6-<(R)-1-hydroxyethyl>carbapen-1-em-3-carboxylate
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
ConditionsYield
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
thienamycin
59995-64-1

thienamycin

Δ1-thienamycin
77171-32-5

Δ1-thienamycin

Conditions
ConditionsYield
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
thienamycin
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

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

Conditions
ConditionsYield
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
thienamycin
59995-64-1

thienamycin

(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
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
ConditionsYield
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
thienamycin
59995-64-1

thienamycin

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

N-<<(p-nitrobenzyl)oxy>carbonyl>-O-<<(p-nitrobenzyl)oxy>carbonyl>thienamycin p-nitrobenzyl ester

Conditions
ConditionsYield
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

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