Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-deoxy-3'-methylene-

Base Information

• Chemical Name: Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-deoxy-3'-methylene-
• CAS No.: 154371-08-1
• Molecular Formula: C32H32N2O6
• Molecular Weight: 540.616
• Mol file: 154371-08-1.mol

Synonyms:

Chemical Property of Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-deoxy-3'-methylene-

Chemical Property:

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-deoxy-3'-methylene-

There total 2 articles about Thymidine, 5'-O-[bis(4-methoxyphenyl)phenylmethyl]-3'-deoxy-3'-methylene- 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: 79.0%

5'-O-(4,4'-dimethoxytrityl)-3'-ketothymidine (154371-07-0) + 1,1-dibromomethane (74-95-3) → 3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-C-methylenethymidine (154371-08-1)

Guidance literature:

With titanium tetrachloride; zinc; In tetrahydrofuran; dichloromethane; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)81816-0

Reference yield:

5'-O-(4-4'-dimethoxytrityl)thymidine (40615-39-2) → 3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-C-methylenethymidine (154371-08-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / pyridinium dichromate, 3A molecular sieves / CH₂Cl₂

2: 79 percent / Zn, TiCl₄ / tetrahydrofuran; CH₂Cl₂

With dipyridinium dichromate; 3 A molecular sieve; titanium tetrachloride; zinc; In tetrahydrofuran; dichloromethane;

Reference yield: 83.0%

Benzyloxymethyl chloride (3587-60-8) + 3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-C-methylenethymidine (154371-08-1) → 3-N-benzyloxymethyl-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-methylenethymidine (583843-88-3)

Guidance literature:

With 1,8-diazabicyclo[4.3.0]non-7-ene; In DMF (N,N-dimethyl-formamide); at 0 - 20 ℃; for 2.5h;

upstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-3'-ketothymidine

1,1-dibromomethane

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

Downstream raw materials:

1-(2,3-dideoxy-5-O-(4,4'-dimethoxytrityl)-3-C-hydroxymethyl-β-D-threo-pentofuranosyl)thymine

5'-O-(4,4'-dimethoxytrityl)-3'-C-(hydroxymethyl)thymidine

1-[(2R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-5-methyl-1H-pyrimidine-2,4-dione

3-N-benzyloxymethyl-3'-deoxy-5'-O-(4,4'-dimethoxytrityl)-3'-methylenethymidine

Refernces

• 1、 Jorgensen,Svendsen,Nielsen,Wengel. "3'-C-hydroxymethylthymidine: Synthesis and incorporation into oligodeoxynucleotide analogues". . p. 921 - 924. Retrieved 2007/10/02.
• 2、 Svendsen,Wengel,Dahl,Kirpekar,Roepstorff. "Oligodeoxynucleotide analogues containing 3'-deoxy-3'-C-threo-hydroxymethylthymidine: Synthesis, hybridization properties and enzymatic stability". . p. 11341 - 11352. Retrieved 2007/10/02.