Product Name

  • Name

    Sultamicillin

  • EINECS 1312995-182-4
  • CAS No. 76497-13-7
  • Article Data1
  • CAS DataBase
  • Density 1.55 g/cm3
  • Solubility
  • Melting Point 190°
  • Formula C25H30N4O9S2
  • Boiling Point 907.7 °C at 760 mmHg
  • Molecular Weight 594.667
  • Flash Point 502.8 °C
  • Transport Information
  • Appearance white to off-white crystalline powder
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 76497-13-7 (Sultamicillin)
  • Hazard Symbols
  • Synonyms 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[(aminophenylacetyl)amino]-3,3-dimethyl-7-oxo-,[[(3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-yl)carbonyl]oxy]methyl ester,S,S-dioxide, [2S-[2a(2R*,5S*),5a,6b(S*)]]-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(2R)-aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-,[[[(2S,5R)-3,3-dimethyl-4,4-dioxido-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-yl]carbonyl]oxy]methylester, (2S,5R,6R)- (9CI);CP 49952;Unacid PD;Unasyn;VD 1827;
  • PSA 216.16000
  • LogP 1.45920

Synthetic route

1,1-dioxopenicillanoyloxymethyl 6-[D-α-(benzylideneaminophenylacetamido)]penicillanate

1,1-dioxopenicillanoyloxymethyl 6-[D-α-(benzylideneaminophenylacetamido)]penicillanate

sultamicillin T
76497-13-7

sultamicillin T

Conditions
ConditionsYield
With girard's reagent P; toluene-4-sulfonic acid In methanol at 20℃; for 0.5h;80%
1,1-dioxopenicillanoyloxymethyl 6-[D-α-(t-butylmethylidenaminophenylacetamido)]penicillanate

1,1-dioxopenicillanoyloxymethyl 6-[D-α-(t-butylmethylidenaminophenylacetamido)]penicillanate

sultamicillin T
76497-13-7

sultamicillin T

Conditions
ConditionsYield
With girard's reagent P; toluene-4-sulfonic acid In methanol at 20℃; for 0.5h;
1,1-dioxopenicillanoyloxymethyl 6-[D-α-(2-furylmethylidenaminophenylacetamido)]penicillanate

1,1-dioxopenicillanoyloxymethyl 6-[D-α-(2-furylmethylidenaminophenylacetamido)]penicillanate

sultamicillin T
76497-13-7

sultamicillin T

Conditions
ConditionsYield
With girard's reagent P; toluene-4-sulfonic acid In methanol at 20℃; for 0.5h;
1,1-dioxopenicillanoyloxymethyl 6-[D-α-(3-pyridylmethylidenaminophenylacetamido)]penicillanate

1,1-dioxopenicillanoyloxymethyl 6-[D-α-(3-pyridylmethylidenaminophenylacetamido)]penicillanate

sultamicillin T
76497-13-7

sultamicillin T

Conditions
ConditionsYield
With girard's reagent P; toluene-4-sulfonic acid In methanol at 20℃; for 0.5h;
1,1-dioxopenicillanoyloxymethyl 6-[D-α-(2-chlorophenylmethylidenaminophenylacetamido)]penicillanate

1,1-dioxopenicillanoyloxymethyl 6-[D-α-(2-chlorophenylmethylidenaminophenylacetamido)]penicillanate

sultamicillin T
76497-13-7

sultamicillin T

Conditions
ConditionsYield
With girard's reagent P; toluene-4-sulfonic acid In methanol at 20℃; for 0.5h;
1,1-dioxopenicillanoyloxymethyl 6-[D-α-(4-chlorophenylmethylidenaminophenylacetamido)]penicillanate

1,1-dioxopenicillanoyloxymethyl 6-[D-α-(4-chlorophenylmethylidenaminophenylacetamido)]penicillanate

sultamicillin T
76497-13-7

sultamicillin T

Conditions
ConditionsYield
With girard's reagent P; toluene-4-sulfonic acid In methanol at 20℃; for 0.5h;
1,1-dioxopenicillanoyloxymethyl 6-[D-α-(2-nitrophenylmethylidenaminophenylacetamido)]penicillanate

1,1-dioxopenicillanoyloxymethyl 6-[D-α-(2-nitrophenylmethylidenaminophenylacetamido)]penicillanate

sultamicillin T
76497-13-7

sultamicillin T

Conditions
ConditionsYield
With girard's reagent P; toluene-4-sulfonic acid In methanol at 20℃; for 0.5h;
1,1-dioxopenicillanoyloxymethyl 6-[D-α-(3-nitrophenylmethylidenaminophenylacetamido)]penicillanate

1,1-dioxopenicillanoyloxymethyl 6-[D-α-(3-nitrophenylmethylidenaminophenylacetamido)]penicillanate

sultamicillin T
76497-13-7

sultamicillin T

Conditions
ConditionsYield
With girard's reagent P; toluene-4-sulfonic acid In methanol at 20℃; for 0.5h;
iodomethyl penicillanate 1,1-dioxide
76247-39-7

iodomethyl penicillanate 1,1-dioxide

sultamicillin T
76497-13-7

sultamicillin T

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.61 g / dimethylformamide / 2 h / 0 °C
2: p-TsOH; Girard-P / methanol / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 1.86 g / dimethylformamide / 2 h / 0 °C
2: 80 percent / p-TsOH; Girard-P / methanol / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 1.53 g / dimethylformamide / 2 h / 0 °C
2: p-TsOH; Girard-P / methanol / 0.5 h / 20 °C
View Scheme
ampicillin sodium salt
69-52-3, 15497-42-4, 54579-43-0, 132437-57-1

ampicillin sodium salt

sultamicillin T
76497-13-7

sultamicillin T

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dimethylformamide / 8 h / 0 °C
2: 1.93 g / dimethylformamide / 2 h / 0 °C
3: p-TsOH; Girard-P / methanol / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: dimethylformamide / 8 h / 0 °C
2: 1.79 g / dimethylformamide / 2 h / 0 °C
3: p-TsOH; Girard-P / methanol / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: dimethylformamide / 8 h / 0 °C
2: 1.81 g / dimethylformamide / 2 h / 0 °C
3: p-TsOH; Girard-P / methanol / 0.5 h / 20 °C
View Scheme
Sodium; (2S,5R,6R)-6-{(R)-2-[2,2-dimethyl-prop-(E)-ylideneamino]-2-phenyl-acetylamino}-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Sodium; (2S,5R,6R)-6-{(R)-2-[2,2-dimethyl-prop-(E)-ylideneamino]-2-phenyl-acetylamino}-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

sultamicillin T
76497-13-7

sultamicillin T

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.61 g / dimethylformamide / 2 h / 0 °C
2: p-TsOH; Girard-P / methanol / 0.5 h / 20 °C
View Scheme
Sodium; (2S,5R,6R)-6-((R)-2-{[1-furan-2-yl-meth-(E)-ylidene]-amino}-2-phenyl-acetylamino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Sodium; (2S,5R,6R)-6-((R)-2-{[1-furan-2-yl-meth-(E)-ylidene]-amino}-2-phenyl-acetylamino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

sultamicillin T
76497-13-7

sultamicillin T

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.79 g / dimethylformamide / 2 h / 0 °C
2: p-TsOH; Girard-P / methanol / 0.5 h / 20 °C
View Scheme
Sodium; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-((R)-2-phenyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Sodium; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-((R)-2-phenyl-2-{[1-phenyl-meth-(E)-ylidene]-amino}-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

sultamicillin T
76497-13-7

sultamicillin T

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.86 g / dimethylformamide / 2 h / 0 °C
2: 80 percent / p-TsOH; Girard-P / methanol / 0.5 h / 20 °C
View Scheme
Sodium; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-((R)-2-phenyl-2-{[1-pyridin-3-yl-meth-(E)-ylidene]-amino}-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Sodium; (2S,5R,6R)-3,3-dimethyl-7-oxo-6-((R)-2-phenyl-2-{[1-pyridin-3-yl-meth-(E)-ylidene]-amino}-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

sultamicillin T
76497-13-7

sultamicillin T

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.93 g / dimethylformamide / 2 h / 0 °C
2: p-TsOH; Girard-P / methanol / 0.5 h / 20 °C
View Scheme
Sodium; (2S,5R,6R)-6-((R)-2-{[1-(2-chloro-phenyl)-meth-(E)-ylidene]-amino}-2-phenyl-acetylamino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Sodium; (2S,5R,6R)-6-((R)-2-{[1-(2-chloro-phenyl)-meth-(E)-ylidene]-amino}-2-phenyl-acetylamino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

sultamicillin T
76497-13-7

sultamicillin T

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.53 g / dimethylformamide / 2 h / 0 °C
2: p-TsOH; Girard-P / methanol / 0.5 h / 20 °C
View Scheme
Sodium; (2S,5R,6R)-6-((R)-2-{[1-(4-chloro-phenyl)-meth-(E)-ylidene]-amino}-2-phenyl-acetylamino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Sodium; (2S,5R,6R)-6-((R)-2-{[1-(4-chloro-phenyl)-meth-(E)-ylidene]-amino}-2-phenyl-acetylamino)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

sultamicillin T
76497-13-7

sultamicillin T

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.81 g / dimethylformamide / 2 h / 0 °C
2: p-TsOH; Girard-P / methanol / 0.5 h / 20 °C
View Scheme
Sodium; (2S,5R,6R)-3,3-dimethyl-6-((R)-2-{[1-(2-nitro-phenyl)-meth-(E)-ylidene]-amino}-2-phenyl-acetylamino)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Sodium; (2S,5R,6R)-3,3-dimethyl-6-((R)-2-{[1-(2-nitro-phenyl)-meth-(E)-ylidene]-amino}-2-phenyl-acetylamino)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

sultamicillin T
76497-13-7

sultamicillin T

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.61 g / dimethylformamide / 2 h / 0 °C
2: p-TsOH; Girard-P / methanol / 0.5 h / 20 °C
View Scheme
Sodium; (2S,5R,6R)-3,3-dimethyl-6-((R)-2-{[1-(3-nitro-phenyl)-meth-(E)-ylidene]-amino}-2-phenyl-acetylamino)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

Sodium; (2S,5R,6R)-3,3-dimethyl-6-((R)-2-{[1-(3-nitro-phenyl)-meth-(E)-ylidene]-amino}-2-phenyl-acetylamino)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylate

sultamicillin T
76497-13-7

sultamicillin T

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.48 g / dimethylformamide / 2 h / 0 °C
2: p-TsOH; Girard-P / methanol / 0.5 h / 20 °C
View Scheme

Sultamicillin Specification

The Sultamicillin, with the CAS registry number 76497-13-7, has the IUPAC name of [(2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]heptane-2-carbonyl]oxymethyl(2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate. For being a kind of white to yellowish white crystalline powder with little odour, it is easily soluble in carbinol or acetonitrile and slightly soluble in ethanol while insoluble in diethyl [ethyl] ether or normal hexane.

The physical properties of this chemical are as follows: (1)ACD/LogP: -0.29; (2)# of Rule of 5 Violations: 2; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 13.82; (7)#H bond acceptors: 13; (8)#H bond donors: 3; (9)#Freely Rotating Bonds: 10; (10)Polar Surface Area: 184.59; (11)Index of Refraction: 1.668; (12)Molar Refractivity: 142.38 cm3; (13)Molar Volume: 381.9 cm3; (14)Polarizability: 56.44 ×10-24 cm3; (15)Surface Tension: 78.4 dyne/cm; (16)Density: 1.55 g/cm3; (17)Flash Point: 502.8 °C; (18)Enthalpy of Vaporization: 132.03 kJ/mol; (19)Boiling Point: 907.7 °C at 760 mmHg; (20)Vapour Pressure: 8.68E-34 mmHg at 25°C; (21)Exact Mass: 594.14542; (22)MonoIsotopic Mass: 594.14542; (23)Topological Polar Surface Area: 216; (24)Heavy Atom Count: 40; (25)Complexity: 1240.

As to its usage, it is widely applied in pharmaceutics. It could be used as semisynthetic penicillin which has the function of antibiosis to pneumococcus, enterococcus, colibacillus, Staphylococcus, Bacillus influenzae and others. And this chemical also applied as the anti-infections medicines.

Additionally, you could obtain the molecular structure by converting the following datas:
(1)Canonical SMILES: CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)OCOC(=O)C4C(S(=O)(=O)C5N4C(=O)C5)(C)C)C
(2)Isomeric SMILES: CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)OCOC(=O)[C@H]4C(S(=O)(=O)[C@H]5N4C(=O)C5)(C)C)C
(3)InChI: InChI=1S/C25H30N4O9S2/c1-24(2)17(29-20(32)16(21(29)39-24)27-19(31)15(26)12-8-6-5-7-9-12)22(33)37-11-38-23(34)18-25(3,4)40(35,36)14-10-13(30)28(14)18/h5-9,14-18,21H,10-11,26H2,1-4H3,(H,27,31)/t14-,15-,16-,17+,18+,21-/m1/s1
(4)InChIKey: OPYGFNJSCUDTBT-PMLPCWDUSA-N 

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