5'-O-(4,4'-DIMETHOXYTRITYL)-2,3'-ANHYDROTHYMIDINE

Base Information

• Chemical Name: 5'-O-(4,4'-DIMETHOXYTRITYL)-2,3'-ANHYDROTHYMIDINE
• CAS No.: 191474-13-2
• Molecular Formula: C31H30 N2 O6
• Molecular Weight: 526.589
• Mol file: 191474-13-2.mol

Synonyms:2,5-Methano-5H,9H-pyrimido[2,1-b][1,5,3]dioxazepin-9-one,3-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-2,3-dihydro-8-methyl-, [2R-(2a,3b,5a)]-

Chemical Property of 5'-O-(4,4'-DIMETHOXYTRITYL)-2,3'-ANHYDROTHYMIDINE

Chemical Property:

• PSA: 81.04000
• LogP: 4.62610

Purity/Quality:

97% ^*data from raw suppliers

5’-O-(4,4’-Dimethoxytrityl)-2,3’-anhydrothymidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 5’-O-(4,4’-Dimethoxytrityl)-2,3’-anhydrothymidine (cas# 191474-13-2) is a compound useful in organic synthesis.

Technology Process of 5'-O-(4,4'-DIMETHOXYTRITYL)-2,3'-ANHYDROTHYMIDINE

There total 13 articles about 5'-O-(4,4'-DIMETHOXYTRITYL)-2,3'-ANHYDROTHYMIDINE 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: 98.0%

5'-O-(4,4'-dimethoxytrityl)-3'-mesyl-2',3'-dideoxythymidine (111647-36-0) → 5'-O-(4,4'-dimethoxytrityl)-2,3'-anhydrothymidine (191474-13-2)

Guidance literature:

With water; potassium phtalimide; In N,N-dimethyl-formamide; at 95 ℃; Inert atmosphere;

DOI:10.1021/jo300045m

Reference yield:

5'-O-(4-4'-dimethoxytrityl)thymidine (40615-39-2) → 5'-O-(4,4'-dimethoxytrityl)-2,3'-anhydrothymidine (191474-13-2)

Guidance literature:

With O-n-octylmethylphosphonochloridothioate; N-ethyl-N,N-diisopropylamine; In pyridine; for 3h; Ambient temperature;

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → 5'-O-(4,4'-dimethoxytrityl)-2,3'-anhydrothymidine (191474-13-2)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 2 h / 20 °C

2: tetrahydrofuran / -8 - 0 °C

3: aq. NaOH / ethanol / 16 h / 80 °C

With pyridine; sodium hydroxide; In tetrahydrofuran; ethanol;

DOI:10.1016/j.bmcl.2007.03.086

upstream raw materials:

5'-O-dimethoxytritylthymidine-3'-O-β-cyanoethoxymethylphosphonite

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

Methanesulfonic acid (2R,3S,5R)-2-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-5-(4-hydroxy-5-methyl-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

5'-O-(4,4'-dimethoxytrityl)-3'-mesyl-2',3'-dideoxythymidine

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-3'-deoxy-3'-fluorothymidine

3’-azido-5’-O-(4,4’-dimethoxytrityl)-3’-deoxythymidine

3'-mercapto-5'-O-DMT-3'-deoxythymidine

C₃₇H₃₆N₂O₆Se

Refernces

• 1、 Teng, Bao,Bai, Yunpeng,Chang, Yu,Chen, Shizhen,Li, Zhaolong. "Technetium-99m-labeling and synthesis of thymidine analogs: Potential candidates for tumor imaging". . p. 3440 - 3444. Retrieved 2008/02/10.
• 2、 Kralikova, Sarka,Masojidkova, Milena,Budesinsky, Milos,Rosenberg, Ivan. "Study on reactivity and protection of the α-hydroxyphosphonate moiety in 5′-nucleotide analogues: Formation of the 3′-O-P-C(OH)-C4′ internucleotide linkage". . p. 329 - 347. Retrieved 2007/10/03.