CAS No.1404-64-4,Sparsomycin Suppliers

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Basic Information

Molecular Structure:
CAS No.:	1404-64-4
Name:	Sparsomycin
Article Data:	8

Formula:	C₁₃H₁₉N₃O₅S₂
Molecular Weight:	361.443
Synonyms:	2-Propenamide,N-[1-(hydroxymethyl)-2-[[(methylthio)methyl]sulfinyl]ethyl]-3-(1,2,3,4-tetrahydro-6-methyl-2,4-dioxo-5-pyrimidinyl)-,[R-[R,S-(E)]]-;5-Pyrimidineacrylamide,1,2,3,4-tetrahydro-N-[1-(hydroxymethyl)-2-[[(methylthio)methyl]sulfinyl]ethyl]-6-methyl-2,4-dioxo-,(E)-(1S)- (8CI);Sparsomycin (7CI);(+)-Sparsomycin;NSC 059729;NSC 59729;U19183;
Density:	1.466 g/cm³
Melting Point:	208-209° (dec)
Hazard Symbols:	T+
Risk Codes:	28
Safety:	28-36/37-45
Transport Information:	UN 2811 6.1/PG 2
PSA:	176.63000
LogP:	0.18770

Synthetic route

: 95407-15-1
O-(methoxymethyl)sparsomycin

: 1404-64-4
sparsomycin

Conditions

Conditions	Yield
With Dowex(R) 50W H(1+) form In methanol at 50℃; for 2h;	74%
With methanol; Dowex 50W at 50℃;	73%
With hydrogenchloride In methanol at 50℃; for 5h;	65%

: 52-90-4
L-Cysteine

: 73-22-3
L-Tryptophan

: 1404-64-4
sparsomycin

Conditions

Conditions	Yield
With Streptomyces sparsogenes var. sparsogenes at 32℃; for 240h; Mechanism; Streptomyces sparsogenes var. spartogenes; other labeled (2)H and (13)C educts;

: 77826-38-1
S-Oxo-S<(methylthio)methyl>-D-cysteinol

: 28277-67-0
(E)-β-(2,4-Dioxo-6-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)acrylic acid

: 1404-64-4
sparsomycin

Conditions

Conditions	Yield
With chloroformic acid ethyl ester; triethylamine 1.) THF/DMF, 0 deg C, 4 h; 2.) THF/DMF, room temp., 48 h; Yield given. Multistep reaction;

: 95407-13-9
(RS)-O-(methoxymethyl)-S-((methylthio)methyl)-D-cysteinol S-oxide

: 1404-64-4
sparsomycin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / dicyclohexyl carbodiimide; 1-hydroxy-7-azabenzotriazole / dimethylformamide / 12 h / 20 °C 2: 74 percent / Dowex(R) 50W H(1+) form / methanol / 2 h / 50 °C View Scheme
Multi-step reaction with 2 steps 1: 38 percent / 1,3-dicyclohexylcarbodiimide, 1-hydroxybenzo-7-azatriazole / tetrahydrofuran; dimethylformamide / Ambient temperature 2: 73 percent / Dowex 50W, MeOH / 50 °C View Scheme
Multi-step reaction with 2 steps 1: tetrahydrofuran; dimethylformamide / 36 h / Ambient temperature 2: 65 percent / 1 N HCl / methanol / 5 h / 50 °C View Scheme

: 626-48-2
6-Methyluracil

ZnCl2: ZnCl2

: 1404-64-4
sparsomycin

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 77 percent / aq. NaOH / H2O / 40 h / 25 °C 2: 60 percent / ceric ammonium nitrate / H2O / 25 °C 3: 75 percent / dimethylsulfoxide / 50 h / 25 °C 4: 90 percent / 3 N aq. NaOH / methanol; dioxane / 24 h / 25 °C 5: 1.) triethylamine / 1.) DMF, THF, 0 deg C, 5 min, 2.) RT, 4 h 6: tetrahydrofuran; dimethylformamide / 36 h / Ambient temperature 7: 65 percent / 1 N HCl / methanol / 5 h / 50 °C View Scheme

Yield

Multi-step reaction with 7 steps
1: 77 percent / aq. NaOH / H2O / 40 h / 25 °C
2: 60 percent / ceric ammonium nitrate / H2O / 25 °C
3: 75 percent / dimethylsulfoxide / 50 h / 25 °C
4: 90 percent / 3 N aq. NaOH / methanol; dioxane / 24 h / 25 °C
5: 1.) triethylamine / 1.) DMF, THF, 0 deg C, 5 min, 2.) RT, 4 h
6: tetrahydrofuran; dimethylformamide / 36 h / Ambient temperature
7: 65 percent / 1 N HCl / methanol / 5 h / 50 °C
View Scheme

: 147-61-5
5-hydroxymethyl-6-methyluracil

: 1404-64-4
sparsomycin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 60 percent / ceric ammonium nitrate / H2O / 25 °C 2: 75 percent / dimethylsulfoxide / 50 h / 25 °C 3: 90 percent / 3 N aq. NaOH / methanol; dioxane / 24 h / 25 °C 4: 1.) triethylamine / 1.) DMF, THF, 0 deg C, 5 min, 2.) RT, 4 h 5: tetrahydrofuran; dimethylformamide / 36 h / Ambient temperature 6: 65 percent / 1 N HCl / methanol / 5 h / 50 °C View Scheme
Multi-step reaction with 4 steps 1: 63 percent / K2S2O8, AgNO3 / H2O / 1.) 90-100 deg C; 2.) room temp. 16 h 2: 40 percent / dimethylformamide / 96 h / Ambient temperature 3: 90 percent / NaOH / methanol; dioxane; H2O / 16 h / 40 °C 4: 1.) Triethylamine, Ethyl chloroformate / 1.) THF/DMF, 0 deg C, 4 h; 2.) THF/DMF, room temp., 48 h View Scheme

: 24048-74-6
1,2,3,4-tetrahydro-6-methyl-2,4-dioxo-5-pyrimidinecarbaldehyde

: 1404-64-4
sparsomycin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 75 percent / dimethylsulfoxide / 50 h / 25 °C 2: 90 percent / 3 N aq. NaOH / methanol; dioxane / 24 h / 25 °C 3: 1.) triethylamine / 1.) DMF, THF, 0 deg C, 5 min, 2.) RT, 4 h 4: tetrahydrofuran; dimethylformamide / 36 h / Ambient temperature 5: 65 percent / 1 N HCl / methanol / 5 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1: 40 percent / dimethylformamide / 96 h / Ambient temperature 2: 90 percent / NaOH / methanol; dioxane; H2O / 16 h / 40 °C 3: 1.) Triethylamine, Ethyl chloroformate / 1.) THF/DMF, 0 deg C, 4 h; 2.) THF/DMF, room temp., 48 h View Scheme

: C11H12N2O6

: 1404-64-4
sparsomycin

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrahydrofuran; dimethylformamide / 36 h / Ambient temperature 2: 65 percent / 1 N HCl / methanol / 5 h / 50 °C View Scheme

: 28277-67-0
(E)-β-(2,4-Dioxo-6-methyl-1,2,3,4-tetrahydropyrimidin-5-yl)acrylic acid

: 1404-64-4
sparsomycin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) triethylamine / 1.) DMF, THF, 0 deg C, 5 min, 2.) RT, 4 h 2: tetrahydrofuran; dimethylformamide / 36 h / Ambient temperature 3: 65 percent / 1 N HCl / methanol / 5 h / 50 °C View Scheme

: 28277-68-1
Ethyl (E)-3-(2,4-Dioxo-6-methyl-5-pyrimidinyl)acrylate

: 1404-64-4
sparsomycin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 90 percent / 3 N aq. NaOH / methanol; dioxane / 24 h / 25 °C 2: 1.) triethylamine / 1.) DMF, THF, 0 deg C, 5 min, 2.) RT, 4 h 3: tetrahydrofuran; dimethylformamide / 36 h / Ambient temperature 4: 65 percent / 1 N HCl / methanol / 5 h / 50 °C View Scheme
Multi-step reaction with 2 steps 1: 90 percent / NaOH / methanol; dioxane; H2O / 16 h / 40 °C 2: 1.) Triethylamine, Ethyl chloroformate / 1.) THF/DMF, 0 deg C, 4 h; 2.) THF/DMF, room temp., 48 h View Scheme

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History

The compound was discovered in 1962 and the structure was determined in 1970; a first total synthesis was reported in 1981.

Specification

The CAS registry number of Sparsomycin is 1404-64-4. In addition, the molecular formula is C₁₃H₁₉N₃O₅S₂ and the molecular weight is 361.44. The IUPAC name is (E)-N-[(2S)-1-hydroxy-3-(methylsulfanylmethylsulfinyl)propan-2-yl]-3-(6-methyl-2,4-dioxo-1H-pyrimidin-5-yl)prop-2-enamide. What's more, it is a nucleotide analogue. Besides, it can be used as an anti-tumor drug and as a tool to study protein synthesis. But it is not usable as an antibiotic.

Physical properties about Sparsomycin are: (1)ACD/LogP: -1.92; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 2.16; (6)ACD/KOC (pH 7.4): 1.96; (7)#H bond acceptors: 8; (8)#H bond donors: 4; (9)#Freely Rotating Bonds: 9; (10)Polar Surface Area: 131.74 Å²; (11)Index of Refraction: 1.656; (12)Molar Refractivity: 90.59 cm³; (13)Molar Volume: 246.4 cm³; (14)Polarizability: 35.91 ×10^-24cm³; (15)Surface Tension: 76.7 dyne/cm; (16)Density: 1.466 g/cm³.

When you are using this chemical, please be cautious about it as the following:
This chemical is very toxic if swallowed. During using it, wear suitable protective clothing and gloves. If contact it with skin, wash it immediately with plenty of ... (to be specified by the manufacturer). And in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.).

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1N/C(=C(/C=C/C(=O)N[C@H](CS(=O)CSC)CO)C(=O)N1)C
(2)Std.InChI: InChI=1S/C13H19N3O5S2/c1-8-10(12(19)16-13(20)14-8)3-4-11(18)15-9(5-17)6-23(21)7-22-2/h3-4,9,17H,5-7H2,1-2H3,(H,15,18)(H2,14,16,19,20)/b4-3+/t9-,23?/m0/s1
(3)Std.InChIKey: XKLZIVIOZDNKEQ-RVUDUMFNSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
dog	LD50	intravenous	1mg/kg (1mg/kg)	"Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory." Vol. 2(6), Pg. -, 1971.
mouse	LD50	intraperitoneal	2400ug/kg (2.4mg/kg)	Cancer Chemotherapy Reports. Vol. 30, Pg. 9, 1963.
mouse	LD50	intravenous	4mg/kg (4mg/kg)	"Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory." Vol. 2(6), Pg. -, 1971.
mouse	LD50	oral	22mg/kg (22mg/kg)	"Compounds Available for Fundamental Research, Volume II-6, Antibiotics, A Program of Upjohn Company Research Laboratory." Vol. 2(6), Pg. -, 1971.