3'-Thymidylic acid, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 4-chlorophenyl 2-cyanoethyl ester

Base Information

• Chemical Name: 3'-Thymidylic acid, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 4-chlorophenyl 2-cyanoethyl ester
• CAS No.: 67221-57-2
• Molecular Formula: C40H39 Cl N3 O10 P
• Molecular Weight: 788.191
• European Community (EC) Number: 266-606-4
• DSSTox Substance ID: DTXSID401117636
• Nikkaji Number: J310.213K
• Mol file: 67221-57-2.mol

Synonyms:67221-57-2;UAWUPJKEJVTXOW-JNTXQERPSA-N;DTXSID401117636;3'-Thymidylic acid, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 4-chlorophenyl 2-cyanoethyl ester

Chemical Property of 3'-Thymidylic acid, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 4-chlorophenyl 2-cyanoethyl ester

Chemical Property:

• PSA: 170.14000
• LogP: 7.31438
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 16
• Exact Mass: 787.2061591
• Heavy Atom Count: 55
• Complexity: 1390

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(O2)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC)OP(=O)(OCCC#N)OC6=CC=C(C=C6)Cl
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)COC(C3=CC=CC=C3)(C4=CC=C(C=C4)OC)C5=CC=C(C=C5)OC)OP(=O)(OCCC#N)OC6=CC=C(C=C6)Cl

Technology Process of 3'-Thymidylic acid, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 4-chlorophenyl 2-cyanoethyl ester

There total 6 articles about 3'-Thymidylic acid, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-, 4-chlorophenyl 2-cyanoethyl ester 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: 77.0%

Phosphorous acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester 4-chloro-phenyl ester 2-cyano-ethyl ester → 5'-O-(dimethoxytrityl)thymidine 3'-(p-chlorphenylcyanoethyl phosphate) (67221-57-2)

Guidance literature:

With iodine; In tetrahydrofuran; water; Ambient temperature;

DOI:10.1016/S0040-4039(00)78985-4

Reference yield:

(p-chlorophenyl) (β-cyanoethyl) phosphorochloridate (69507-62-6) + 5'-O-(4-4'-dimethoxytrityl)thymidine (40615-39-2) → 5'-O-(dimethoxytrityl)thymidine 3'-(p-chlorphenylcyanoethyl phosphate) (67221-57-2)

Guidance literature:

With 1-methyl-1H-imidazole; In acetonitrile; at 20 ℃; for 2h;

Reference yield:

p-chlorophenyl phosphorodichloridite (32666-92-5) → 5'-O-(dimethoxytrityl)thymidine 3'-(p-chlorphenylcyanoethyl phosphate) (67221-57-2)

Guidance literature:

Multi-step reaction with 3 steps

1: lutidine-2,6 / tetrahydrofuran / -78 °C

2: lutidine-2,6 / tetrahydrofuran / -20 °C

3: 77 percent / I₂ / tetrahydrofuran; H₂O / Ambient temperature

With 2,6-dimethylpyridine; iodine; In tetrahydrofuran; water;

DOI:10.1016/S0040-4039(00)78985-4

upstream raw materials:

(p-chlorophenyl) (β-cyanoethyl) phosphorochloridate

5'-O-(4-4'-dimethoxytrityl)thymidine

3-Hydroxypropionitrile

4-chlorophenylphosphorodichloridate

Downstream raw materials:

N-benzoyl-5'-O-(bis(4-methoxyphenyl)phenylmethyl)-P-(4-chlorophenyl)-2'-deoxycytidylyl-(3'->5')-3'-thymidylic acid, 4-chlorophenyl 2-cyanoethyl ester

N-benzoyl-5'-O-(bis(4-methoxyphenyl)phenylmethyl)-P-(4-chlorophenyl)-2'-deoxyadenylyl-(3'->5')-3'-thymidylic acid, 4-chlorophenyl 2-cyanoethyl ester

C₄₁H₄₀Cl₂N₆O₁₅P₂

<(MeO)2Tr>TpTOAc

Refernces

• 1、 Bernardini, Silvio De,Waldmeier, Felix,Tamm, Christoph. "Nucleosides and Nucleotides. Part 17. A Simple Preparation of Protected Deoxynucleoside-3'-phosphates". . p. 2142 - 2147. Retrieved 2007/10/02.