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3373-59-9

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3373-59-9 Usage

General Description

L-Threonine methyl ester is a chemical compound that is derived from the amino acid L-threonine. It is a white crystalline substance that is commonly used in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals. L-threonine methyl ester is known for its role as a building block in the formation of various proteins and enzymes in biological systems. It is also used as a chiral reagent in organic synthesis and as a precursor in the production of various pharmaceutical compounds. Additionally, L-threonine methyl ester has potential applications in the fields of medicine, nutrition, and biotechnology.

Check Digit Verification of cas no

The CAS Registry Mumber 3373-59-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,3,7 and 3 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 3373-59:
(6*3)+(5*3)+(4*7)+(3*3)+(2*5)+(1*9)=89
89 % 10 = 9
So 3373-59-9 is a valid CAS Registry Number.
InChI:InChI=1/C5H11NO3/c1-3(7)4(6)5(8)9-2/h3-4,7H,6H2,1-2H3

3373-59-9SDS

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 L-THREONINE METHYL ESTER

1.2 Other means of identification

Product number -
Other names L-Threonine methyl

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:3373-59-9 SDS

3373-59-9Synthetic route

methanol
67-56-1

methanol

L-threonine
72-19-5

L-threonine

L-threonine methyl ester
3373-59-9

L-threonine methyl ester

Conditions
ConditionsYield
With thionyl chloride at 0℃; for 25h; Temperature; Reflux;80%
With hydrogenchloride Heating;
With hydrogenchloride for 5h; Heating; Yield given;
N-(tert-butoxycarbonyl)-l-threonine methyl ester
60538-19-4, 79479-07-5, 96099-84-2, 113525-91-0

N-(tert-butoxycarbonyl)-l-threonine methyl ester

L-threonine methyl ester
3373-59-9

L-threonine methyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid In acetone at 10 - 25℃; for 2h;70%
methanol
67-56-1

methanol

(3S,6R,1''S)-5-ethoxy-3-(1''-hydroxyethyl)-6-methyl-3,6-dihydro-1H-pyrazine-2-one

(3S,6R,1''S)-5-ethoxy-3-(1''-hydroxyethyl)-6-methyl-3,6-dihydro-1H-pyrazine-2-one

B

L-threonine methyl ester
3373-59-9

L-threonine methyl ester

Conditions
ConditionsYield
Multistep reaction;
L-threonine
72-19-5

L-threonine

L-threonine methyl ester
3373-59-9

L-threonine methyl ester

Conditions
ConditionsYield
With thionyl chloride In methanol
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

trityl chloride
76-83-5

trityl chloride

methyl (2S,3R)-3-hydroxy-2-triphenylmethylaminobutanoate
74481-55-3

methyl (2S,3R)-3-hydroxy-2-triphenylmethylaminobutanoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;100%
With triethylamine In chloroform at 20℃; Alkylation; triphenylmethylation; tritylation;89%
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

(4S,5R)-4-[(Z)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-carboxy-but-1-enylcarbamoyl]-2,2,5-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
670233-20-2

(4S,5R)-4-[(Z)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-carboxy-but-1-enylcarbamoyl]-2,2,5-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(4S,5R)-4-[(Z)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-((1S,2R)-2-hydroxy-1-methoxycarbonyl-propylcarbamoyl)-but-1-enylcarbamoyl]-2,2,5-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
670233-21-3

(4S,5R)-4-[(Z)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-1-((1S,2R)-2-hydroxy-1-methoxycarbonyl-propylcarbamoyl)-but-1-enylcarbamoyl]-2,2,5-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine100%
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

L-threonine methyl ester hydrochloride
39994-75-7

L-threonine methyl ester hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In methanol at 20℃; for 18h; Inert atmosphere;100%
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

Allyl chloroformate
2937-50-0

Allyl chloroformate

N-Allyloxycarbonyl-L-threonine methyl ester
221351-00-4

N-Allyloxycarbonyl-L-threonine methyl ester

Conditions
ConditionsYield
With triethylamine In acetonitrile at 0 - 20℃; for 18.5h; Substitution;98%
N-acetyl-(S)-alanine cyanomethyl ester
60397-83-3

N-acetyl-(S)-alanine cyanomethyl ester

L-threonine methyl ester
3373-59-9

L-threonine methyl ester

C10H18N2O5

C10H18N2O5

Conditions
ConditionsYield
With acetic acid In tetrahydrofuran for 16h; Microwave irradiation;98%
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

N-methyl-N-(benzyloxycarbonyl)-D-leucine
65635-85-0

N-methyl-N-(benzyloxycarbonyl)-D-leucine

-threonine methyl ester
120448-64-8

-threonine methyl ester

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane97%
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

methyl chloroformate
79-22-1

methyl chloroformate

(2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acid
1007881-21-1

(2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoic acid

Conditions
ConditionsYield
With sodium hydroxide In water at 0℃; for 12h;97%
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

C8H9F6NO3

C8H9F6NO3

C10H18N2O5

C10H18N2O5

Conditions
ConditionsYield
With acetic acid In tetrahydrofuran at 70℃; for 4h; Temperature; Microwave irradiation;96%
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

benzoyl chloride
98-88-4

benzoyl chloride

N-benzoyl-L-threonine methyl ester
79893-89-3

N-benzoyl-L-threonine methyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 12h;95%
With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃;
With sodium hydrogencarbonate In 1,4-dioxane; water at 0℃;
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

L-threonine methyl ester
3373-59-9

L-threonine methyl ester

N-(tert-butoxycarbonyl)-l-threonine methyl ester
60538-19-4, 79479-07-5, 96099-84-2, 113525-91-0

N-(tert-butoxycarbonyl)-l-threonine methyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane95%
With sodium hydrogencarbonate In methanol; water at 20℃; for 20h;92%
With triethylamine In dichloromethane
With triethylamine In water; acetonitrile at 0 - 20℃;8.08 g
With triethylamine In methanol at 10 - 35℃;
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

Boc-D-Phe-OH
18942-49-9

Boc-D-Phe-OH

N-Boc-L-Phe-L-Thr-O-Me
73763-45-8

N-Boc-L-Phe-L-Thr-O-Me

Conditions
ConditionsYield
Stage #1: Boc-D-Phe-OH With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: L-threonine methyl ester In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 18h;
95%
2,6-dichloropyridine-3-carboxylic acid
38496-18-3

2,6-dichloropyridine-3-carboxylic acid

L-threonine methyl ester
3373-59-9

L-threonine methyl ester

(2S,3R)-N-[(2,6-dichloropyridin-3-yl)carbonyl]threonine methyl ester

(2S,3R)-N-[(2,6-dichloropyridin-3-yl)carbonyl]threonine methyl ester

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0℃; for 5h; Inert atmosphere;94%
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

C7H10F3NO3

C7H10F3NO3

C10H18N2O5

C10H18N2O5

Conditions
ConditionsYield
With acetic acid In tetrahydrofuran for 16h; Microwave irradiation;94%
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

Z(OMe)-Lys(Z)-OH
42533-12-0

Z(OMe)-Lys(Z)-OH

Z(OMe)-Lys(Z)-Thr-OMe

Z(OMe)-Lys(Z)-Thr-OMe

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane93%
With dicyclohexyl-carbodiimide
(2-oxocyclopent)acetic acid
104115-44-8

(2-oxocyclopent)acetic acid

L-threonine methyl ester
3373-59-9

L-threonine methyl ester

(2R,3S,5aR,8aS)-2-methyl-4-oxo-octahydro-1-oxa-3a-aza-cyclopenta[c]pentalene-3-carboxylic acid methyl ester
1240492-81-2

(2R,3S,5aR,8aS)-2-methyl-4-oxo-octahydro-1-oxa-3a-aza-cyclopenta[c]pentalene-3-carboxylic acid methyl ester

Conditions
ConditionsYield
at 110℃; under 11251.1 Torr; Meyer synthesis; Microwave irradiation; optical yield given as %de;93%
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

C8H10F5NO3

C8H10F5NO3

C10H18N2O5

C10H18N2O5

Conditions
ConditionsYield
With acetic acid In tetrahydrofuran for 16h; Microwave irradiation;93%
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

1-benzotriazolyl 3β-hydroxyolean-12-en-28-oate
1596377-01-3

1-benzotriazolyl 3β-hydroxyolean-12-en-28-oate

C35H57NO5

C35H57NO5

Conditions
ConditionsYield
With sodium carbonate In N,N-dimethyl-formamide at 20℃; for 0.333333h;93%
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

N-(Benzyloxycarbonyl)glycine
1138-80-3

N-(Benzyloxycarbonyl)glycine

Cbz-Gly-L-Thr-OMe
41961-03-9

Cbz-Gly-L-Thr-OMe

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide92%
Stage #1: N-(Benzyloxycarbonyl)glycine With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: L-threonine methyl ester In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 18h;
86%
With Sephadex G-50; triethylamine; bromelain In ethyl acetate at 37℃; for 7h;50%
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

ethyl benzimidate hydrochloride
5333-86-8

ethyl benzimidate hydrochloride

(4S,5R)-4-methyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester
60538-17-2, 62107-40-8, 74272-77-8, 79952-14-0, 79952-15-1, 82659-84-5, 88336-08-7

(4S,5R)-4-methyl-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid methyl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 24h;92%
In chloroform for 12h; Heating;85%
L-N-Boc-Ala
15761-38-3

L-N-Boc-Ala

L-threonine methyl ester
3373-59-9

L-threonine methyl ester

methyl (tert-butoxycarbonyl)-L-alanyl-L-threoninate
41938-15-2

methyl (tert-butoxycarbonyl)-L-alanyl-L-threoninate

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In ethyl acetate Acylation;92%
Stage #1: L-N-Boc-Ala With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane for 0.75h;
Stage #2: L-threonine methyl ester With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;
82%
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

(4S,5R)-3-((benzyloxy)carbonyl)-2,2,5-trimethyloxazolidine-4-carboxylic acid
160821-18-1

(4S,5R)-3-((benzyloxy)carbonyl)-2,2,5-trimethyloxazolidine-4-carboxylic acid

(4S,5R)-4-((1S,2R)-2-Hydroxy-1-methoxycarbonyl-propylcarbamoyl)-2,2,5-trimethyl-oxazolidine-3-carboxylic acid benzyl ester
670233-30-4

(4S,5R)-4-((1S,2R)-2-Hydroxy-1-methoxycarbonyl-propylcarbamoyl)-2,2,5-trimethyl-oxazolidine-3-carboxylic acid benzyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide92%
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

(3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid
66863-43-2

(3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid

(S)-tert-butyl 3-((2S)-3-hydroxy-1-methoxy-1-oxobutan-2-ylcarbamoyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate
900865-75-0

(S)-tert-butyl 3-((2S)-3-hydroxy-1-methoxy-1-oxobutan-2-ylcarbamoyl)-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 18h;92%
Stage #1: (3S)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid With benzotriazol-1-ol In tetrahydrofuran at 0℃; for 0.166667h;
Stage #2: L-threonine methyl ester With 4-methyl-morpholine; dicyclohexyl-carbodiimide In tetrahydrofuran at 0 - 20℃; for 18h;
87%
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

(2R,3R)-2-Benzyloxycarbonylamino-3-phenyl-pent-4-enoic acid

(2R,3R)-2-Benzyloxycarbonylamino-3-phenyl-pent-4-enoic acid

(2S,3R)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-pent-4-enoylamino)-3-hydroxy-butyric acid methyl ester

(2S,3R)-2-((S)-2-Benzyloxycarbonylamino-3-phenyl-pent-4-enoylamino)-3-hydroxy-butyric acid methyl ester

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; triethylamine In dichloromethane90.2%
Hippuric Acid
495-69-2

Hippuric Acid

L-threonine methyl ester
3373-59-9

L-threonine methyl ester

Bz-Gly-Thr-OMe
115494-73-0

Bz-Gly-Thr-OMe

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide90%
C15H18N2O5

C15H18N2O5

L-threonine methyl ester
3373-59-9

L-threonine methyl ester

(R/S)-tert-butyl-5-((2S,3R)-3-hydroxy-1-methoxy-1-oxobutan-2-ylcarbamoyl)-3-oxo-2-phenylpyrazolidine-1-carboxylate
1126476-83-2

(R/S)-tert-butyl-5-((2S,3R)-3-hydroxy-1-methoxy-1-oxobutan-2-ylcarbamoyl)-3-oxo-2-phenylpyrazolidine-1-carboxylate

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 0 - 20℃; for 10h;90%
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

(S)-4-amino-3-(2-(tert-butoxycarbonylamino)-4-phenylbutanamido)benzoic acid
1449786-45-1

(S)-4-amino-3-(2-(tert-butoxycarbonylamino)-4-phenylbutanamido)benzoic acid

(2S,3R)-methyl 2-(4-amino-3-((S)-2-(tert-butoxycarbonylamino)-4-phenylbutanamido) benzamido)-3-hydroxybutanoate
1449786-48-4

(2S,3R)-methyl 2-(4-amino-3-((S)-2-(tert-butoxycarbonylamino)-4-phenylbutanamido) benzamido)-3-hydroxybutanoate

Conditions
ConditionsYield
With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 12h; Inert atmosphere;90%
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

C14H13F6NO3

C14H13F6NO3

C16H22N2O5

C16H22N2O5

Conditions
ConditionsYield
With acetic acid In tetrahydrofuran at 70℃; for 5h; Microwave irradiation;90%
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

methylpropioimidate hydrochloride
39739-45-2

methylpropioimidate hydrochloride

(S)-2-Ethyl-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

(S)-2-Ethyl-5-methyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester

Conditions
ConditionsYield
In dichloromethane for 24h; Ambient temperature;89%
L-threonine methyl ester
3373-59-9

L-threonine methyl ester

4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

N-(p-methoxybenzyl)-L-threonine methyl ester
936362-61-7

N-(p-methoxybenzyl)-L-threonine methyl ester

Conditions
ConditionsYield
With sodium cyanoborohydride; acetic acid In methanol at 0 - 20℃; for 17h;89%
N,N-diethyl(α,α-difluoro-4-methoxybenzyl)amine
928150-63-4

N,N-diethyl(α,α-difluoro-4-methoxybenzyl)amine

L-threonine methyl ester
3373-59-9

L-threonine methyl ester

methyl (4S,5R)-2-(4-methoxyphenyl)-5-methyl-4,5-dihydrooxazole-4-carbonylate
704910-29-2

methyl (4S,5R)-2-(4-methoxyphenyl)-5-methyl-4,5-dihydrooxazole-4-carbonylate

Conditions
ConditionsYield
In dichloromethane at 40℃; for 1h;89%

3373-59-9Relevant articles and documents

Clickable glycopeptoids for synthesis of glycopeptide mimic

Singhamahapatra, Anadi,Sahoo, Laxminarayan,Loganathan, Duraikkannu

, p. 10329 - 10336 (2013)

Structurally diverse novel glycopeptoids were synthesized which can be attached to biologically important peptides by click reaction to improve their potential to be used in medicinal chemistry. Triazole-linked αβ-hydrid glycopeptoids were synthesized that mimic the conserved linkage region of N-linked glycoproteins in eukaryotes. The amide bonds were replaced with triazole rings, and αβ-hybrid peptoids were introduced as the backbone modification in peptidomimetics. In addition to their facile synthesis, these modifications have the possibility of introducing otherwise impossible conformations in the peptide backbone.

Synthesis of Ethyl cis-2--7-oxo-3-phenyl-6-phthalimido-1-azabicyclohept-3-ene-2-carboxylate and Methyl cis-2-Bromo-3-methyl-8-oxo-7-phthalimido-4-oxa-1-azabicyclooctane-2-carboxylate

Hakimelahi, Gholam H.,Jarrahpour, Ali A.

, p. 1501 - 1505 (1989)

Th synthesis of Δ1-carbapenem and two β-lactams possessing a Br-atom at the N-substituting center not involved in the lactam ring and bearing the carboxyl group is described.The β-lactams having this kind of Br-substitution are more susceptible to nucleophilic attack than those having a conjugated double bond with the N-atom of the β-lactam ring.DBU is found to be an excellent reagent for the elimination of the silyloxy function.Moreover, a simple method for the addition of diethyl phosphite to an α,β-unsaturated double bond using a catalytic amount of NaH is described.

Visible-Light Mediated Tryptophan Modification in Oligopeptides Employing Acylsilanes

Reimler, Jannik,Studer, Armido

supporting information, p. 15392 - 15395 (2021/10/04)

A method for the selective tryptophan modification and labelling of tryptophan-containing peptides is described. Photoirradiation of acylsilanes generates reactive siloxycarbenes which undergo H?N-insertion into the indole moiety of tryptophan to give stable silyl protected hemiaminals. This method is successfully applied to chemically modify various tryptophan containing oligopeptides. The method enables the selective introduction of alkynes to peptides that are eligible for further alkyne-azide click chemistry. In addition, the dansyl fluorophore can be conjugated to a peptide using this approach.

NOVEL TRITERPENE DERIVATIVES AS HIV INHIBITORS

-

Page/Page column 34, (2020/08/28)

The present invention relates to novel triterpene derivatives of formula (I); and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R4, and ring are as defined herein. The invention also relates to novel triterpene derivatives, related compounds, and pharmaceutical compositions useful for the therapeutic treatment of viral diseases and particularly HIV mediated diseases.

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