CAS No.59995-64-1,Thienamycin Suppliers

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Basic Information

Molecular Structure:
CAS No.:	59995-64-1
Name:	Thienamycin
Article Data:	13

Formula:	C11H16 N2 O4 S
Molecular Weight:	272.325
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;
EINECS:	203-170-6
Density:	1.5g/cm³
Boiling Point:	514°C at 760 mmHg
Flash Point:	264.7°C
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

Total:50 Page 1 of 2 1 2 Next>>

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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.