17579-99-6

Usage

Uses

1. Used in Chemical Synthesis:
METHYLTRIPHENOXYPHOSPHONIUM IODIDE is used as a reagent for the transformation of the 5'-hydroxyl group in nucleosides to the 5'-deoxy-5'-iodo group. This transformation is crucial in the synthesis of various nucleoside analogs, which have potential applications in the development of new drugs and therapeutic agents.
2. Used in Pharmaceutical Industry:
In the pharmaceutical industry, METHYLTRIPHENOXYPHOSPHONIUM IODIDE is used as a key intermediate in the synthesis of antiviral, anticancer, and anti-inflammatory drugs. The conversion of the 5'-hydroxyl group to the 5'-deoxy-5'-iodo group allows for the creation of modified nucleosides that can be incorporated into these therapeutic agents, enhancing their efficacy and selectivity.
3. Used in Research and Development:
METHYLTRIPHENOXYPHOSPHONIUM IODIDE is also employed in research and development laboratories for the study of nucleoside chemistry and the development of novel nucleoside-based compounds. Its ability to modify nucleosides makes it a valuable tool for exploring new chemical reactions and potential applications in various fields, including medicine, biotechnology, and materials science.
4. Used in Diagnostic Applications:
In the field of diagnostics, METHYLTRIPHENOXYPHOSPHONIUM IODIDE can be used to develop new assays and tests for the detection and monitoring of various diseases. The modified nucleosides produced using METHYLTRIPHENOXYPHOSPHONIUM IODIDE can be labeled with fluorescent or radioactive tags, allowing for the sensitive and specific detection of target molecules in biological samples.

Purification Methods

Gently heat the impure iodide with good grade Me2CO. The saturated solution obtained is decanted rapidly from undissolved salt and treated with an equal volume of dry Et2O. The iodide separates as flat needles which are collected by centrifugation, washed several times with dry Et2O, and dried in a vacuum over P2O5. For this recrystallisation it is essential to minimise the time of contact with Me2CO and to work rapidly and with rigorous exclusion of moisture. If the crude material is to be used, it should be stored under dry Et2O, and dried and weighed in vacuo immediately before use. [Landauer & Rydon J Chem Soc 224 1953, Hudson et al. J Chem Soc Perkin Trans 1 982 1974, Beilstein 6 IV 704.]

InChI:InChI=1/C19H18O3P/c1-23(20-17-11-5-2-6-12-17,21-18-13-7-3-8-14-18)22-19-15-9-4-10-16-19/h2-16H,1H3/q+1

Synthetic route

triphenyl phosphite (101-02-0) + methyl iodide (74-88-4) → methyltriphenoxyphosphonium iodide (17579-99-6)

Conditions	Yield
im geschlossenen Rohr;

tert-butyl (4S,7S,10aS)-7-formyl-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate (1400677-76-0) + methyltriphenoxyphosphonium iodide (17579-99-6) → tert-butyl (4S,7S,10aS)-5-oxo-7-vinyloctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate (1400677-77-1)

Conditions	Yield
Stage #1: methyltriphenoxyphosphonium iodide With potassium hexamethylsilazane In tetrahydrofuran; toluene at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: tert-butyl (4S,7S,10aS)-7-formyl-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate In tetrahydrofuran; toluene at -78 - 20℃; for 3h;	91%

methyltriphenoxyphosphonium iodide (17579-99-6) + 2-benzyloxycarbonylamino-3-hydroxy-propionic Acid tert-butyl Ester (59859-77-7) → 2-benzyloxycarbonylamino-3-iodo-propionic Acid tert-butyl Ester

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 3.5h;	85%

methyltriphenoxyphosphonium iodide (17579-99-6) + 2-amino-phenol (95-55-6) → 2-methyl-2',3'-dihydro-3H-2λ5-[2,2']spirobi(benzo[1,3,2]oxazaphosphole) (57602-63-8)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane	75%

2'-fluoro-uridine + methyltriphenoxyphosphonium iodide (17579-99-6) → 2',5'-Dideoxy-5'-iodo-2'-fluorouridine

Conditions	Yield
In methanol; chloroform; N,N-dimethyl-formamide	58%

ethanol (64-17-5) + methyltriphenoxyphosphonium iodide (17579-99-6) → diphenyl methylphosphonate (7526-26-3) + ethyl iodide (75-03-6) + phenol (108-95-2)

3-isopropyl-pentane-1,5-diol (61898-54-2, 83805-51-0) + methyltriphenoxyphosphonium iodide (17579-99-6) → 1-iodo-3-(2-iodo-ethyl)-4-methyl-pentane (98998-09-5)

p-methylsulfonylbenzyl alcohol (22821-77-8) + methyltriphenoxyphosphonium iodide (17579-99-6) → (4-iodomethyl-phenyl)-methyl sulfone (100960-84-7)

3β-acetoxy-6α-hydroxymethyl-5α-pregnan-20-one (1805-11-4, 96611-57-3, 103188-73-4) + methyltriphenoxyphosphonium iodide (17579-99-6) → 3β-acetoxy-6α-iodomethyl-5α-pregnan-20-one (103129-42-6)

Conditions	Yield
With methyl iodide

methyltriphenoxyphosphonium iodide (17579-99-6) → diphenyl methylphosphonate (7526-26-3)

Conditions	Yield
at 220℃;
With sodium hydroxide
With sodium hydroxide
With butan-1-ol In acetonitrile at -40℃;

methyltriphenoxyphosphonium iodide (17579-99-6) + dimethyl amine (124-40-3) → dimethylamino-methyl-diphenoxy-phosphonium; iodide

methyltriphenoxyphosphonium iodide (17579-99-6) + diethylamine (109-89-7) → diethyl-(methyl-diphenoxy-phosphoranyliden)-ammonium; iodide (20442-20-0, 857012-64-7)

methyltriphenoxyphosphonium iodide (17579-99-6) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8) → 4-iodomethyl-2,2-dimethyl-[1,3]dioxolane (23737-52-2)

cholesterol (57-88-5) + methyltriphenoxyphosphonium iodide (17579-99-6) + methyl iodide (74-88-4) → cholesteryl iodide (2930-80-5)

6,6-diphenyl-2,3,5,6-tetrahydro-imidazo[2,1-b]thiazol-5-ol (62506-10-9) + methyltriphenoxyphosphonium iodide (17579-99-6) → 6,6-diphenyl-2,3,5,6-tetrahydro-imidazo[2,1-b]thiazole (62476-40-8)

Conditions	Yield
With sodium cyanoborohydride In N,N,N,N,N,N-hexamethylphosphoric triamide

2,2'-Anhydrouridine (3736-77-4) + methyltriphenoxyphosphonium iodide (17579-99-6) → methylphosphonic acid (3aS)-2t-iodomethyl-6-oxo-(3ar,9ac)-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-3c-yl ester phenyl ester (24453-29-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 0.25h;

methyltriphenoxyphosphonium iodide (17579-99-6) → C19H17O3P*INa

Conditions	Yield
With sodium hydride In tetrahydrofuran 1.) 50-60 deg C, 2.) RT, overnight;

methyltriphenoxyphosphonium iodide (17579-99-6) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → diphenyl methylphosphonate (7526-26-3) + methyltetraphenoxyphosphorane (58373-32-3) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) + methyl iodide (74-88-4)

Conditions	Yield
In dichloromethane for 2h; Ambient temperature;

methyltriphenoxyphosphonium iodide (17579-99-6) + 4-methylcyclohexylamine (6321-23-9) → C22H45N3P(1+)*I(1-)

methyltriphenoxyphosphonium iodide (17579-99-6) + but-2t(?)-en-1-ol → (E)-crotyl iodide (38169-04-9)

Conditions	Yield
at 0℃;

methyltriphenoxyphosphonium iodide (17579-99-6) + toluene (108-88-3) + sodium → methylphosphine (593-54-4)

Conditions	Yield
anschliessendes Behandeln mit wss. Methanol;

methyltriphenoxyphosphonium iodide (17579-99-6) + furan-2,3,5(4H)-trione pyridine (1:1) → diphenyl methylphosphonate (7526-26-3) + hydrogen iodide (10034-85-2) + phenol (108-95-2)

2,6-dimethylpyridine (108-48-5) + hexanes-EtOAc + methyltriphenoxyphosphonium iodide (17579-99-6) + 5'-O-(tert-butydiphenylsilyl)-3'-deoxy-3'-C-(hydroxymethyl)-2'-O-(2-methoxyethyl)-5-methyluridine (318246-92-3) → 5'-O-(tert-butydiphenylsilyl)-3'-deoxy-3'-C-(iodomethyl)-2'-O-(2-methoxyethyl)-5-methyluridine (312934-29-5)

Conditions	Yield
In ethyl acetate; N,N-dimethyl-formamide
In ethyl acetate; N,N-dimethyl-formamide

methyltriphenoxyphosphonium iodide (17579-99-6) + methyl 4-(4-hydroxy-1-butyl)phenylacetate (164931-20-8) → methyl 4-(4-iodobutyl)phenylacetate (192804-76-5)

Conditions	Yield
In hexane; ethyl acetate; acetonitrile	4.12 g (71%)

morpholine (110-91-8) + 4-N-[4-(2-hydroxyethyl)phenyl]amino-5-phenyl-7-(2,3-O-(methylethylidene)-β-D-erythrofuranosyl)pyrrolo[2,3-d]pyrimidine (186457-13-6) + methyltriphenoxyphosphonium iodide (17579-99-6) → 4-N-[4-(2-(4-morpholino)ethyl)phenyl]amino-5-phenyl-7-(2,3-O-(methylethylidene)-β-D-erythrofuranosyl)pyrrolo[2,3-d]pyrimidine (186457-14-7)

Conditions	Yield
With sodium thiosulfate In 1,4-dioxane; dichloromethane

2-(β-hydroxy-β-phenylethyl)morpholine (58040-33-8) + ethereal oxalic acid + methyltriphenoxyphosphonium iodide (17579-99-6) → 2-(β-phenyl-trans-vinyl)morpholine hydrogen oxalate (58039-41-1, 58040-34-9)

Conditions	Yield
In N,N,N,N,N,N-hexamethylphosphoric triamide

methyltriphenoxyphosphonium iodide (17579-99-6) + silver trifluoromethanesulfonate (2923-28-6) → Methyl-triphenoxyphosphonium-trifluormethansulfonat (58973-90-3)

Conditions	Yield
byproducts: AgI;
byproducts: AgI;

1-(2-methoxy-5-(trifluoromethyl)phenyl)ethan-1-one (503464-99-1) + methyltriphenoxyphosphonium iodide (17579-99-6) → 1-methoxy-2-(prop-1-en-2-yl)-4-(trifluoromethyl)benzene

Conditions	Yield
Stage #1: methyltriphenoxyphosphonium iodide With potassium tert-butylate In tetrahydrofuran at 0℃; for 2h; Stage #2: 1-(2-methoxy-5-(trifluoromethyl)phenyl)ethan-1-one In tetrahydrofuran at 20℃; for 1h;

Upstream product

• 101-02-0 triphenyl phosphite 
• 74-88-4 methyl iodide 

Downstream Products

• 100960-84-7 (4-iodomethyl-phenyl)-methyl sulfone 
• 7526-26-3 diphenyl methylphosphonate 
• 857012-64-7 diethyl-(methyl-diphenoxy-phosphoranyliden)-ammonium; iodide 
• 2930-80-5 cholesteryl iodide 
• 62476-40-8 6,6-diphenyl-2,3,5,6-tetrahydro-imidazo[2,1-b]thiazole 
• 593-54-4 methylphosphine 
• 312934-29-5 5'-O-(tert-butydiphenylsilyl)-3'-deoxy-3'-C-(iodomethyl)-2'-O-(2-methoxyethyl)-5-methyluridine 
• 58039-41-1 2-(β-phenyl-trans-vinyl)morpholine hydrogen oxalate 
• 58973-90-3 Methyl-triphenoxyphosphonium-trifluormethansulfonat 
• 186457-14-7 4-N-[4-(2-(4-morpholino)ethyl)phenyl]amino-5-phenyl-7-(2,3-O-(methylethylidene)-β-D-erythrofuranosyl)pyrrolo[2,3-d]pyrimidine 
• 192804-76-5 methyl 4-(4-iodobutyl)phenylacetate 
• 10034-85-2 hydrogen iodide 
• 108-95-2 phenol 
• 58373-32-3 methyltetraphenoxyphosphorane