40615-36-9

Basic information

• Product Name: 4,4'-Dimethoxytrityl chloride
• Synonyms: (DMT-C1) 4,4'-DiMethoxytrityl chloride;4,4'-(Chloro(phenyl)Methylene)bis(Methoxybenzene);DMT-Cl)D;4,4- twoMethoxy threephenylMethyl chloride;DMT-Cl, 98%, pink color;4,4'-DiMethoxytrityl chloride SynonyMs 1,1'-(ChlorophenylMethylene)bis[4-Methoxybenzene];Anti-Dematin, C-Terminal antibody produced in rabbit;EPB49
• CAS NO: 40615-36-9
• Molecular Formula: C₂₁H₁₉ClO₂
• Molecular Weight: 338.83
• EINECS: 255-002-6
• Product Categories: OLED materials,pharm chemical,electronic;Organics;Coupling Reagent;N-Protecting Reagents;Biochemistry;Nucleosides, Nucleotides & Related Reagents;Protecting Agents for Hydroxyl and Amino Groups;Protecting Agents, Phosphorylating Agents & Condensing Agents;Protection & Derivatization Reagents (for Synthesis);Synthetic Organic Chemistry;Regant series
• Mol File: 40615-36-9.mol

Chemical Properties

• Melting Point: 123-125 °C
• Boiling Point: 455.07°C (rough estimate)
• Flash Point: 155.6 °C
• Appearance: Pink/Powder
• Density: 1.0887 (rough estimate)
• Vapor Pressure: 0Pa at 20℃
• Refractive Index: 1.5330 (estimate)
• Storage Temp.: Store at 0°C
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• Water Solubility: Soluble in chloroform and methanol. Partially soluble in water
• Sensitive: Moisture Sensitive
• Stability: Hygroscopic, Moisture Sensitive
• BRN: 2471942
• CAS DataBase Reference: 4,4'-Dimethoxytrityl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4,4'-Dimethoxytrityl chloride(40615-36-9)
• EPA Substance Registry System: 4,4'-Dimethoxytrityl chloride(40615-36-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-34
• Safety Statements: 22-24/25-37/39-26-36-45-36/37/39
• RIDADR: 3261
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 40615-36-9(Hazardous Substances Data)

Usage

Uses

Used in Oligonucleotide Synthesis:
4,4'-Dimethoxytrityl chloride is used as a protective reagent for oligonucleotide synthesis. It plays a crucial role in the selective protection and deprotection of thiol and hydroxy groups in nucleoside derivatives, ensuring the successful synthesis of oligonucleotides with desired properties and functions.
Used in Nucleoside and Nucleotide Protection:
In the chemical synthesis of nucleosides and nucleotides, 4,4'-Dimethoxytrityl chloride acts as a hydroxyl protecting group. This protection is essential to prevent unwanted side reactions and ensure the correct formation of the desired molecular structures, which are vital for various biological and pharmaceutical applications.

Flammability and Explosibility

Notclassified

Purification Methods

DMT crystallises from cyclohexane/acetyl chloride as the hydrochloride. Dry it over KOH pellets in a desiccator. When dissolved in *C6H6 and air is blown through, HCl is removed. It crystallises from Et2O. [Baeyer & Villiger Chem Ber 36 2788 1903, Smith et al. J Am Chem Soc 84 430 1962, Smith et al. J Am Chem Soc 85 3821 1963.] Ifit has hydrolysed considerably (see OH in IR), then repeat the crystallisation from cyclohexane/acetyl chloride — excess of AcCl is removed in a vacuum over KOH, then recrystallise it from Et2O. [Beilstein 6 IV 1042.]

Synthetic route

4,4'-dimethoxytrityl alcohol (40615-35-8) → 4,4'-dimethoxytrityl chloride (40615-36-9)

Conditions	Yield
With thionyl chloride In n-heptane 1.) 0 deg C, 10 min, 2.) RT, 10 min, 3.) reflux, 1 h;	91%
With acetyl chloride In toluene for 2h; Inert atmosphere; Reflux;	89.7%
With thionyl chloride In diethyl ether Heating;	82%

methoxybenzene (100-66-3) + Benzotrichlorid (98-07-7) → 4,4'-dimethoxytrityl chloride (40615-36-9)

Conditions	Yield
Stage #1: methoxybenzene; Benzotrichlorid With aluminum (III) chloride at 30℃; for 10h; Large scale; Stage #2: With hydrogenchloride In water at 30℃; for 3h; Large scale; Stage #3: With oxalyl dichloride for 6h; Temperature; Concentration; Reflux; Large scale;	85.13%

4,4'-dimethoxytrityl cation (14039-15-7) → 4,4'-dimethoxytrityl chloride (40615-36-9)

Conditions	Yield
With perchloric acid; water; sodium chloride In methanol at 25℃; Equilibrium constant; other temperatures;

methoxybenzene (100-66-3) + 2-chloro-decalin → 4,4'-dimethoxytrityl chloride (40615-36-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) AlCl3, 2.) aq. H2SO4 / 1.) 2 h 2: AcCl / 1.5 h / Heating View Scheme

Benzotrichlorid (98-07-7) → 4,4'-dimethoxytrityl chloride (40615-36-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) AlCl3, 2.) aq. H2SO4 / 1.) 2 h 2: AcCl / 1.5 h / Heating View Scheme

4-Methoxybenzophenone (611-94-9) → 4,4'-dimethoxytrityl chloride (40615-36-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / Grignard reaction 2: 82 percent / SOCl2 / diethyl ether / Heating View Scheme

1-bromo-4-methoxy-benzene (104-92-7) + sodium → 4,4'-dimethoxytrityl chloride (40615-36-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 72 percent / Grignard reaction 2: 82 percent / SOCl2 / diethyl ether / Heating View Scheme

4,4'-dimethoxytrityl chloride (40615-36-9) + 1-(2-C-cyano-2-deoxy-β-D-arabinofuranosyl)thymine (140858-91-9) → 1-<2-C-cyano-2-deoxy-5-O-(dimethoxytrityl)-β-D-arabinofuranosyl>thymine (140859-04-7)

Conditions	Yield
With pyridine for 1.5h; Ambient temperature;	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-deoxy-2'-fluorouridine (56287-17-3, 69123-94-0, 784-71-4) → 2'-deoxy-2'-fluoro-5'-O-(4,4'-dimethoxytrityl)uridine (146954-74-7)

Conditions	Yield
With pyridine at 20℃; for 3h; Inert atmosphere;	100%
With pyridine at 20℃; for 3h; Inert atmosphere;	100%
With dmap at 20℃; for 16h;	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + 4-[4-(4-Hydroxy-butylcarbamoyloxymethyl)-2-methoxy-5-nitro-phenoxy]-butyric acid methyl ester (176375-53-4) → 4-(4-{4-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-butylcarbamoyloxymethyl}-2-methoxy-5-nitro-phenoxy)-butyric acid methyl ester (176375-44-3)

Conditions	Yield
With pyridine at 50℃; for 1h;	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + (R)-oxiranemethanol (57044-25-4) → (S)-glycidyl 4,4’-dimethoxytrityl ether (834906-31-9)

Conditions	Yield
With triethylamine In dichloromethane for 12h;	100%
With pyridine at 20℃;	89%
In dichloromethane; triethylamine Ambient temperature;	65%

4,4'-dimethoxytrityl chloride (40615-36-9) + 5',3'-O-(tetraisopropyldisiloxane-1,3-di-yl)-1-β-D-arabinofuranosyl-uracil (104477-70-5) → 1-[2'-O-(4,4'-Dimethoxytrityl)-3',5',-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-arabinofuranosyl]uracil (194031-42-0)

Conditions	Yield
With pyridine; silver nitrate In tetrahydrofuran	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + N-[9-((2R,4S,5R)-4-Hydroxy-5-hydroxymethyl-5-phenylselanyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-benzamide (201420-68-0) → N-(9-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-5-phenylselanyl-tetrahydro-furan-2-yl}-9H-purin-6-yl)-benzamide (201420-69-1)

Conditions	Yield
In pyridine for 48h; Ambient temperature;	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + 5'-O-(4-nitrobenzoyl)thymidine (5983-14-2) → 3'-O-(4,4'-dimethoxytrityl)-5'-O-(4-nitrobenzoyl)thymidine (180335-81-3)

Conditions	Yield
With pyridine; dmap at 20℃; for 49h; tritylation;	100%

methyl (R)-3-hydroxy-2-methylpropionate (72657-23-9) + 4,4'-dimethoxytrityl chloride (40615-36-9) → (R)-3-[Bis-(4-methoxy-phenyl)-phenyl-methoxy]-2-methyl-propionic acid methyl ester (286458-65-9)

Conditions	Yield
With 2,3,5-trimethyl-pyridine In dichloromethane at 25℃; Substitution;	100%
With pyridine at 20℃; for 4h;
With 2,4,6-trimethyl-pyridine In dichloromethane at 0℃;

4,4'-dimethoxytrityl chloride (40615-36-9) + N-[6-dimethylamino-9-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-2-phenoxy-acetamide (375345-64-5) → N-(9-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-dimethylamino-9H-purin-2-yl)-2-phenoxy-acetamide (375345-67-8)

Conditions	Yield
With pyridine at 20℃; for 2h;	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + 1-<(2R,4R,5R)-4-<(benzoyloxy)methyl>-5-(2-hydroxyethyl)tetrahydrofuran-2-yl>uracil (129399-14-0) → Benzoic acid (2R,3R,5R)-2-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-ethyl}-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-ylmethyl ester

Conditions	Yield
With triethylamine In tetrahydrofuran	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2-(2-O,4-C-methylene-β-D-ribofuranosyl)-1-isoquinolone (402859-75-0) → 2-[5-O-(4,4'-dimethoxytrityl)-2-O,4-C-methylene-β-D-ribofuranosyl]-1-isoquinolone (600707-57-1)

Conditions	Yield
With pyridine at 20℃; for 3h;	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-deoxy-2'-C-β-methyl-N4-benzoylcytidine (596112-06-0) → 5'-O-(dimethoxytrityl)-2'-deoxy-2'-C-β-methyl-N4-benzoylcytidine (596112-07-1)

Conditions	Yield
With pyridine at 20℃;	100%
With pyridine

4,4'-dimethoxytrityl chloride (40615-36-9) + 1-(2-O,2-C-propano-β-D-arabinofuranosyl)uracil (664333-53-3) → 1-[5-O-(4,4'-dimethoxytrityl)-2-O,2-C-propano-β-D-arabinofuranosyl]uracil (664333-54-4)

Conditions	Yield
With pyridine at 20℃; for 12h;	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2-[(2S,3R,5S)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-isoindole-1,3-dione → 1-[2,3-dideoxy-6-O-(tert-butyldimethylsilyl)-5-O-(4,4'-dimethoxytrityl)-3-phthalimido-α-D-arabino-hexofuranosyl]thymine (676132-95-9)

Conditions	Yield
With pyridine; silver nitrate In tetrahydrofuran at 20℃; for 48h;	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2'-O,4'-C-propylene-5-methyluridine (634153-97-2) → 5'-O-(4,4'-dimethoxytrityl)-2'-O,4'-C-propylene-5-methyluridine (634153-98-3)

Conditions	Yield
With pyridine at 40℃;	100%

3',5'-O-(1,1,3,3-tetra-isopropyldisiloxane-1,3-diyl)adenosine (69304-45-6) + 4,4'-dimethoxytrityl chloride (40615-36-9) → 3',5'-O-(1,1,3,3-tetraisopropyl-1,3-disiloxanediyl)-6-N-(4,4'-dimethoxytrityl)-adenosine (874889-86-8)

Conditions	Yield
With pyridine at 20℃; for 14h;	100%
With pyridine at 20℃; for 14h;	91%

2,2-Dimethyl-propionic acid 4-((2R,4S,5R)-4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-imidazol-1-ylmethyl ester + 4,4'-dimethoxytrityl chloride (40615-36-9) → [4-(5-O-DMT-2-deoxy-D-β-ribofuranosyl)imidazolyl]methyl 2,2-dimethylpropionate (872088-48-7)

Conditions	Yield
With pyridine; dmap; triethylamine at 20℃; for 2h;	100%
With pyridine; dmap; triethylamine at 20℃;	146 mg

[4-(2-O-allyl-β-D-ribofuranosyl)imidazol-1-yl]methyl 2,2-dimethylpropiolate (872088-52-3) + 4,4'-dimethoxytrityl chloride (40615-36-9) → 2,2-Dimethyl-propionic acid 4-{(2S,3R,4R,5R)-3-allyloxy-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-imidazol-1-ylmethyl ester (872088-53-4)

Conditions	Yield
With pyridine; dmap; triethylamine at 20℃; for 19h;	100%

1-[4-(tert-butyl-dimethyl-silanyloxy)-5-(1,2-dihydroxy-ethyl)-tetrahydro-furan-2-yl]-6-methyl-1H-pyrimidine-2,4-dione + 4,4'-dimethoxytrityl chloride (40615-36-9) → 1-[5-{2-[bis-(4-methoxy-phenyl)-phenyl-methoxy]-1-hydroxy-ethyl}-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-6-methyl-1H-pyrimidine-2,4-dione

Conditions	Yield
With pyridine at 20℃; for 12h;	100%

5-methyl-2'-O,4'-C-(methylenoxymethylene)uridine (519056-25-8) + 4,4'-dimethoxytrityl chloride (40615-36-9) → 5'-O-(4,4'-dimethoxytrityl)-5-methyl-2'-O,4'-C-(methylenoxymethylene)uridine (519056-26-9)

Conditions	Yield
With pyridine at 20℃; for 3h;	100%
With pyridine In nitrogen at 20℃; for 3h;	100%

N-[6-(2-cyano-ethylsulfanyl)-9-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-2-phenoxy-acetamide (138406-86-7) + 4,4'-dimethoxytrityl chloride (40615-36-9) → N-[9-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-(2-cyano-ethylsulfanyl)-9H-purin-2-yl]-2-phenoxy-acetamide (138406-87-8)

Conditions	Yield
With pyridine at 20℃; for 2h;	100%

N-1-{(1R,2S,3S,4R)-2,3-bis(methoxymethoxy)-4-(hydroxymethyl)cyclopentyl}-5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylideneadenosine (933060-58-3) + 4,4'-dimethoxytrityl chloride (40615-36-9) → (CH3)3CSi(CH3)2OCH2C5H4O3(CH3)2C5H3N5C5H6CH2OC(C6H4OCH3)2C6H5(OCH2OCH3)2

Conditions	Yield
With pyridine at 20℃; for 0.166667h;	100%

N-1-{(1R,2S,3S,4R)-2-(methoxymethoxy)-3-methoxy-4-(hydroxymethyl)cyclopentyl}-5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylideneadenosine (933060-59-4) + 4,4'-dimethoxytrityl chloride (40615-36-9) → (CH3)3CSi(CH3)2OCH2C5H4O3(CH3)2C5H3N5C5H6CH2OC(C6H4OCH3)2C6H5OCH3OCH2OCH3

Conditions	Yield
With pyridine at 20℃;	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + 3-hydroxymethyl-benzoic acid (3006-96-0) → triethylammonium 4-[[(4,4'-dimethoxytrityl)oxy]methyl]benzoate (403730-30-3)

Conditions	Yield
Stage #1: 4,4'-dimethoxytrityl chloride; 3-hydroxymethyl-benzoic acid In pyridine at 20℃; Stage #2: With triethylammonium acetate In methanol; dichloromethane; water	100%

2-(2-hydroxyethoxy)acetic acid (13382-47-3) + 4,4'-dimethoxytrityl chloride (40615-36-9) → triethylammonium 2-[2-(4,4'-dimethoxytrityloxy)ethoxy] acetate (403730-25-6)

Conditions	Yield
Stage #1: 2-(2-hydroxyethoxy)acetic acid; 4,4'-dimethoxytrityl chloride In pyridine at 20℃; Stage #2: With triethylammonium acetate In methanol; dichloromethane; water	100%

4,4'-dimethoxytrityl chloride (40615-36-9) + (4S,5R)-4-Hydroxy-5-hydroxymethyl-pyrrolidin-2-one (1020110-06-8) → C26H27NO5 (1020110-07-9)

Conditions	Yield
With pyridine at 20℃; for 12h;	100%

N-1-{(1R,2S,3R)-4-hydroxymethyl-2,3-isopropylidenedioxycyclopent-4-en-1-yl}-5'-O-(tert-butyldimethylsilyl)-2',3'-O-isopropylideneadenosine (1022895-51-7) + 4,4'-dimethoxytrityl chloride (40615-36-9) → C49H61N5O9Si

Conditions	Yield
With pyridine at 20℃;	100%
With pyridine at 20℃; for 10h;

1-(2-deoxy-2-fluoro-4-thio-β-D-ribofuranosyl)uracil (1030358-61-2) + 4,4'-dimethoxytrityl chloride (40615-36-9) → 1-[5-O-(4,4'-dimethoxytrityl)-2-deoxy-2-fluoro-4-thio-β-D-ribofuranosyl]uracil

Conditions	Yield
In pyridine at 20℃; for 2h;	100%

3-(2-hydroxyethoxy)propionic acid (89211-34-7) + 4,4'-dimethoxytrityl chloride (40615-36-9) + triethylammonium acetate (5204-74-0) → triethylammonium 3-[2-[2-(4,4'-dimethoxytrityloxy)]ethoxy]propionate (403730-26-7)

Conditions	Yield
Stage #1: 3-(2-hydroxyethoxy)propionic acid; 4,4'-dimethoxytrityl chloride In pyridine at 20℃; Stage #2: triethylammonium acetate In methanol; dichloromethane; water	100%

(2R,3S)-2-(hydroxymethyl)tetrahydrofuran-3-ol (91547-59-0) + 4,4'-dimethoxytrityl chloride (40615-36-9) → 5-O-(4,4'-dimethoxytriphenylmethyl)-1,4-anhydro-2-deoxy-D-ribitol (95049-01-7)

Conditions	Yield
With pyridine at 20℃; for 12h;	100%
With pyridine at 20℃; for 12h;	75%
With pyridine at 20℃; for 12h;	75%
With pyridine at 20℃; for 12h;

Upstream product

• 14039-15-7 4,4'-dimethoxytrityl cation 
• 40615-35-8 4,4'-dimethoxytrityl alcohol 
• 100-66-3 methoxybenzene 
• 98-07-7 Benzotrichlorid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 611-94-9 4-Methoxybenzophenone 

Downstream Products

• 40615-35-8 4,4'-dimethoxytrityl alcohol 
• 56499-54-8 2-(Dimethoxytributylamino)-ethyl-1-phosphat 
• 162604-83-3 1,3-dimethyl-5'-O-(4,4'-dimethoxytrityl)-2'-deoxy-ψ-uridine 
• 7500-76-7 4,4'-dimethoxytriphenylmethane 
• 125016-87-7 bis(4-methoxyphenyl)phenylmethyl methyl ether 
• 120510-52-3 2-(4,4'-dimethoxytrityloxymethyl)-6-(hydroxymethyl)pyridine 
• 118364-69-5 2',5'-bis-O-(t-butyldimethylsilyl)-N⁶-(4,4'-dimethoxytrityl)adenosine 
• 71933-62-5 5'-O-(dimethoxytrityl)-2'-O-(tetrahydropyranyl)-N²-benzoylguanosine 
• 133931-96-1 (2R,3S,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-5-(6-chloro-9H-purin-9-yl)tetrahydrofuran-3-ol 
• 73793-98-3 5'-O-(4,4'-dimethoxytrityl)-N⁶-dimethylaminomethyleneadenosine 
• 125697-62-3 4-Nitrophenyl 4-(4,4'-dimethoxytrityloxy)-butyrate 
• 130506-40-0 benzyl 3,4-O-isopropylidene-6-O-(4,4'-dimethoxytrityl)-β-D-galactopyranoside 
• 122955-98-0 allyl 6-O-(4,4'-dimethoxytriphenylmethyl)-β-D-galactopyranoside 
• 129466-77-9 9-<2-(4,4'-Dimethoxytrityloxy)ethyl>acridin 

Relevant articles and documents

Process for the capture and reuse of the 4,4′-dimethoxytriphenylmethyl group during manufacturing of oligonucleotides

In a standard amidite coupling-based automated oligonucleotide synthesis campaign, the 4,4′-dimethoxytriphenylmethyl (DMT) protecting group is discarded as waste along with large amounts of dichloromethane. Herein, we report a straightforward and simple process for complete capture and recovery of the DMT group and dichloromethane, rendering the oligonucleotide manufacturing process safer and more economical.

Efficient separation and purification method of 4,4'-dimethoxytrityl chloride and 4,4'-dimethoxytrityl alcohol

The invention provides an efficient separation and purification method of 4,4'-dimethoxytrityl chloride and 4,4'-dimethoxytrityl alcohol. According to the method, a target product with high purity isprepared on the basis of ensuring high reaction yield, impurity components contained in the target product are clarified, the content of the impurity components is controlled, and particularly the content of hydroxyl impurities and the content of acetylated impurities are controlled to be 0.05% or less.

Synthesis method of high-purity 4, 4 '-dimethoxytriphenylchloromethane

The invention provides a synthesis method of high-purity 4, 4 '-dimethoxytriphenylchloromethane, which comprises the following steps: by using anisole and trichlorotoluene as initial raw materials, carrying out F-C reaction, hydrochloric acid hydrolysis reaction and chlorination reaction to prepare a DMT-Cl crude product of which the purity is higher than 98.5%, and carrying out solvent crystallization to obtain a DMT-Cl finished product of which the purity is higher than 99.9%, thereby obtaining the DMT-Cl finished product yield higher than 98%. According to the method provided by the invention, on the basis of ensuring high reaction yield, the target product is prepared with high purity, impurity components contained in the target product are clear, the content of the impurity componentsis controlled, and particularly, hydroxyl impurities and acetylated impurities are controlled to be 0.05% or below.

Industrial method for preparing and purifying 4,4'-dimethoxytrityl chloride

The invention discloses an industrial method for preparing and purifying 4,4'-dimethoxytrityl chloride. According to the industrial method, benzaldehyde and trichlorotoluene are adopted as initial raw materials, a crude product of DMT-CL (4,4'-Dimethoxytrityl Chloride) is prepared through F-C reaction, hydrochloric acid hydrolysis reaction and chlorination reaction, the purity of the crude product of DMT-CL is greater than 98.5%, a finished product of DMT-CL of which the purity is greater than 99.9% is prepared by crystallizing the crude product of DMT-CL with a solvent, and the yield of the finished product of DMT-CL is greater than 80%. The industrial method for preparing and purifying 4,4'-dimethoxytrityl chloride is reasonable in design, grignard reagents or refined solvents which are relatively expensive are not used, the purpose that the high-purity DMT-CL is safely, environmental-friendly and industrially produced is achieved, and application as a high-quality standard hydroxyl protection agent for biological nucleoside and nucleotide is met.

Post-synthetic modification of nucleic acids by inverse Diels-Alder reaction

The present invention concerns a method and a kit for the post-synthetic modification of nucleic acids via an inverse Diels-Alder reaction.

Boronic acid containing oligonucleotides and polynucleotides

The present invention relates to the field of nucleic acid immobilization, purification and detection and, more particularly, to boronic acid modified oligonucleotides and polynucleotides useful in bioconjugation reactions. The modified oligonucleotides and polynucleotides are useful in reactions for the immobilization and purification of macromolecules.

A new method for synthesis of 4,4'-dimethoxytrityl chloride

The selection of appropriate protecting groups forms an essential part of oligonucleotide synthesis. 4,4'-Dimethoxytrityl group (DMT-), originally developed by Khorana at al., is still the most frequently used acid labile protecting group for selective blocking of 5'-hydroxyl function of the sugar moiety in the nucleosides or nucleotides.The conventional method of synthesis of 4,4'-dimethoxytrityl chloride (DMTCl, 7), involves the reaction of ethyl benzoate with anisyl magnesium bromide in dry benzene to give the crude product, di-p-anisylphenyl carbinol as a reddish oil which is subsequently converted into DMTCl on refluxing with acetyl chloride.

Molar Absorptivity and pKR+ of the 4,4'-Dimethoxytrityl Carbenium Ion in Methanolic Water, and its Equilibrium with Chloride Ion

The 4,4'-dimethoxytrityl carbenium ion has been generated in 80:20 (v/v) water-methanol containing perchloric acid in a rapid reaction from 4,4'-dimethoxytrityl alcohol and in a slower reaction from 4,4'-dimethoxytritylamine.The pK (-0.95; K=8.98) and molar absorptivity (ε=297 000) of the cation have been measured directly under equilibrium conditions in this highly aqueous medium at ionic strength = 1.0 mol dm-3 by a convenient spectrophotometric method at 25 deg C.In addition, the pK has been measured at other temperatures, which allows the determination of the standard enthalpy (ΔH = -11.4 kJ mol-1) and entropy (ΔS = -20 J K-1 mol-1) of the reaction of the cation with the solvent, and at other ionic strengths.The equilibrium constant for the formation of 4,4'-dimethoxytrityl chloride from the cation and chloride has also been measured in the same medium (KRCl = 8.20 at 25.0 deg C, ionic strength = 1.0 mol dm-3) by generating the cation from the alcohol and perchloric acid in the presence of 0.10 mol dm-3 sodium chloride.

Efficient synthesis of azetidine through N-trityl- or N- dimethoxytritylazetidines starting from 3-amino-1-propanol or 3- halopropylamine hydrohalides

Efficient synthetic routes for the preparation of azetidine starting from commercially available 3-amino-1-propanol or 3-halopropylamine hydrohalides are reported. First, the appropriate N-trityl- or N-dimethoxytrityl protected tosyloxy- or halopropylamines were prepared. These precursors were then cyclized into the N-trityl- or N-dimethoxytritylazetidines. The N-protecting groups were removed in the presence of perchloric acid giving the hydrogen perchlorate salt of azetidine. The latter compound was transformed into its free base using a strong base under anhydrous conditions. The relatively expensive 4,4'-dimethoxytrityl chloride and less expensive trityl chloride used in these synthetic procedures were recycled in good yields. Azetidine hydrogenperchlorate can be used to prepare N-substituted azetidines without the need to isolate the free azetidine.

Reactions of some p-Substituted Triphenylmethyl Chlorides with Alcohols, Alkali-metal Alcoholates, and Tributylamine

The p-methoxylated triphenylmethyl chlorides (4a-c), when heated with alcohols, give mixtures of the corresponding triarylmethanes (5a-c) (via the hydride transfer to the corresponding triarylmethylium cations) and the alkyl (substituted triphenylmethyl) ethers (7a-c) (via polar susbtitution reactions).Part or all of the ether (7c) may be further converted into the substituted triphenylmethanol (6c).In the reaction of the mono-p-methoxylated halides (4a) and (4c) with methanol, the substitution products (7a) and (7c) are formed as the main products, while the main product of the reaction of the di-p-methoxylated halide (4b) with methanol is the substituted triphenylmethane (5b).When the methanol is replaced by 2H4> methanol, no reduction product is formed from the halide (4c).Reaction of halide (4c) with ethanol furnishes exclusively the substituted triphenylmethane (5c).The p-chlorophenyl(diphenyl)methyl chloride (4d) gives, with methanol, mainly or exclusively the ether (7d), and with ethanol, under mild conditions, gives the ether (9d).However, under vigorous conditions, the substituted triphenylmethane (5d) is formed.The reduction of the p-methoxylated triphenylmethyl chloride (4c) by alcohols as well as its conversion into alkyl (p-methoxylated triphenylmethyl) ethers are accompanied, to a certain degree, by exchange of the p-methoxy group of the substrate and the alkoxy group of the alcohol; no similar exchange of the p-chlorine atom of halide (4d) was observed.Explanations for all obsrved diferences are offered.The reactions of the substituted triphenylmethyl chlorides (4b-d) with alkoxides in the corresponding alcohols give the corresponding alkyl (substituted triphenylmethyl) ethers (7b), (7c), (9c), and (9d), respectively, in excellent yields.The reaction of the triarylmethyl chloride (4d) with potassiumt-butoxide in THF in the presence of acetone led, among other products, to the formation of oligomeric material which indicates the operation of single-electron-transfer induced processes.Reaction of the same chloride (4d) with tributylamine in refluxing cumene or t-butylbenzene led to the exclusive formation of a series of products all of which may be derived from the intermediacy of the substituted triphenylmethyl radical (18); the latter, in turn, is thought to arise as a result of dissociative electron transfer from tributylamine to chloride (4d).