((2S,6R)-6-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)-4-tritylmorpholin-2-yl)methyl dimethylphosphoramidochloridate

Base Information

• Chemical Name: ((2S,6R)-6-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)-4-tritylmorpholin-2-yl)methyl dimethylphosphoramidochloridate
• CAS No.: 956139-21-2
• Molecular Formula: C37H37ClN5O5P
• Molecular Weight: 698.158
• European Community (EC) Number: 851-175-2
• UNII: WGS8BF4AGW
• Nikkaji Number: J3.138.017K
• Mol file: 956139-21-2.mol

Synonyms:956139-21-2;((2S,6R)-6-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)-4-tritylmorpholin-2-yl)methyl dimethylphosphoramidochloridate;N,N-DimethylphosphoramidochloridicAcid[(2S,6R)-6-[4-(Benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-4-(triphenylmethyl)-2-morpholinyl]methylEster;Dimethyl-phosphoramidochloridic acid 6-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-4-trityl-morpholin-2-ylmethyl ester;N,N-Dimethylphosphoramidochloridic acid [(2S,6R)-6-[4-(benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-4-(triphenylmethyl)-2-morpholinyl]methyl ester;N-[1-[(2R,6S)-6-[[chloro(dimethylamino)phosphoryl]oxymethyl]-4-tritylmorpholin-2-yl]-2-oxopyrimidin-4-yl]benzamide;starbld0008284;WGS8BF4AGW;MORPHOLINO C SUBUNIT;MFCD30475589;E73716;(6-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)-4-tritylmorpholin-2-yl)methyldimethylphosphoramidochloridate;[(2S,6R)-6-[4-(Benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-4-(triphenylmethyl)-2-morpholinyl]methyl N,N-dimethylphosphoramidochloridate;N,N-Dimethylphosphoramidochloridic Acid [(2S,6R)-6-[4-(Benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-4-(tri;N-[1-[(2R,6S)-6-[[chloro(dimethylamino)phosphoryl]oxymethyl]-4-trityl-morpholin-2-yl]-2-oxo-pyrimidin-4-yl]benzamide;Phosphoramidochloridic acid, N,N-dimethyl-, [(2S,6R)-6-[4-(benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-4-(triphenylmethyl)-2-morpholinyl]methyl ester

Chemical Property of ((2S,6R)-6-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)-4-tritylmorpholin-2-yl)methyl dimethylphosphoramidochloridate

Chemical Property:

• PKA: 8.63±0.20(Predicted)
• Density: 1.30±0.1 g/cm3(Predicted)
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 11
• Exact Mass: 697.2220840
• Heavy Atom Count: 49
• Complexity: 1190

Purity/Quality:

97% ^*data from raw suppliers

N,N-DimethylphosphoramidochloridicAcid[(2S,6R)-6-[4-(Benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-4-(triphenylmethyl)-2-morpholinyl]methylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CN(C)P(=O)(OCC1CN(CC(O1)N2C=CC(=NC2=O)NC(=O)C3=CC=CC=C3)C(C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl
• Isomeric SMILES: CN(C)P(=O)(OC[C@@H]1CN(C[C@@H](O1)N2C=CC(=NC2=O)NC(=O)C3=CC=CC=C3)C(C4=CC=CC=C4)(C5=CC=CC=C5)C6=CC=CC=C6)Cl
• Uses: N,N-Dimethylphosphoramidochloridic Acid [(2S,6R)-6-[4-(Benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-4-(triphenylmethyl)-2-morpholinyl]methyl Ester is an oligonucleotide analog having cationic intersubunit linkages for use in antisense modulation of gene expression. Also a potential antibacterial.

Technology Process of ((2S,6R)-6-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)-4-tritylmorpholin-2-yl)methyl dimethylphosphoramidochloridate

There total 3 articles about ((2S,6R)-6-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)-4-tritylmorpholin-2-yl)methyl dimethylphosphoramidochloridate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 74.0%

N-{1-[(2R,6)-6-(hydroxymethyl)-4-tritylmorpholin-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}benzamide (125515-31-3) + N,N-dimethylphosphoroamidic dichloride (677-43-0) → phosphoramidochloridic acid, N,N-dimethyl-, [6-[4-(benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-4-(triphenylmethyl)-2-morpholinyl]methyl ester (956139-21-2)

Guidance literature:

N-{1-[(2R,6)-6-(hydroxymethyl)-4-tritylmorpholin-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}benzamide; With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium bromide; In dichloromethane; acetonitrile; at 0 ℃; for 0.0333333h; Inert atmosphere;

N,N-dimethylphosphoroamidic dichloride; In dichloromethane; acetonitrile; at 0 ℃; for 0.416667h; Inert atmosphere;

DOI:10.1016/j.tetlet.2012.09.126

Reference yield:

N4-benzoylcytidine (13089-48-0) → phosphoramidochloridic acid, N,N-dimethyl-, [6-[4-(benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-4-(triphenylmethyl)-2-morpholinyl]methyl ester (956139-21-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium periodate / methanol / 0.17 h / 60 °C

1.2: 3 h / 60 °C

2.1: triethylamine / acetonitrile / 1 h / 0 °C

3.1: lithium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile; dichloromethane / 1 h / 0 °C / Inert atmosphere

With sodium periodate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium bromide; In methanol; dichloromethane; acetonitrile;

DOI:10.1002/bkcs.11958

Reference yield:

C16H18N4O4*C7H8O3S (166239-52-7) → phosphoramidochloridic acid, N,N-dimethyl-, [6-[4-(benzoylamino)-2-oxo-1(2H)-pyrimidinyl]-4-(triphenylmethyl)-2-morpholinyl]methyl ester (956139-21-2)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / acetonitrile / 1 h / 0 °C

2: lithium bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile; dichloromethane / 1 h / 0 °C / Inert atmosphere

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium bromide; In dichloromethane; acetonitrile;

DOI:10.1002/bkcs.11958

upstream raw materials:

N-{1-[(2R,6)-6-(hydroxymethyl)-4-tritylmorpholin-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}benzamide

N,N-dimethylphosphoroamidic dichloride

N₄-benzoylcytidine

C₁₆H₁₈N₄O₄*C₇H₈O₃S