5'(S)-{N⁴-[1-(4-azidobutyl)]cytosin-1-yl}-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester

Base Information

• Chemical Name: 5'(S)-{N⁴-[1-(4-azidobutyl)]cytosin-1-yl}-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester
• CAS No.: 389128-30-7
• Molecular Formula: C₂₂H₃₄N₆O₄S
• Molecular Weight: 478.616
• Mol file: 389128-30-7.mol

Synonyms:5'(S)-{N⁴-[1-(4-azidobutyl)]cytosin-1-yl}-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester

Chemical Property of 5'(S)-{N⁴-[1-(4-azidobutyl)]cytosin-1-yl}-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'(S)-{N⁴-[1-(4-azidobutyl)]cytosin-1-yl}-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester

There total 2 articles about 5'(S)-{N⁴-[1-(4-azidobutyl)]cytosin-1-yl}-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl 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: 76.0%

4-azidobutan-1-amine (88192-20-5) + 5'(S)-[O4-(2,4,6-triisopropylbenzenesulfonyl)uracil-1-yl]-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester (389128-29-4) → 5'(S)-{N4-[1-(4-azidobutyl)]cytosin-1-yl}-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester (389128-30-7)

Guidance literature:

In dichloromethane; at 0 ℃; for 0.75h;

DOI:10.1016/S0040-4020(01)00800-6

Reference yield:

5'(S)-(uracil-1-yl)-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester (389128-28-3) → 5'(S)-{N4-[1-(4-azidobutyl)]cytosin-1-yl}-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester (389128-30-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / 4-DMAP; Et₃N / CH₂Cl₂ / 12 h / 20 °C

2: 76 percent / CH₂Cl₂ / 0.75 h / 0 °C

With dmap; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4020(01)00800-6

Reference yield:

5'(S)-{N4-[1-(4-azidobutyl)]cytosin-1-yl}-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester (389128-30-7) → 5'(S)-{N4-[1-(4-azidobutyl)]cytosin-1-yl}-2'(R)-dibenzyl-oxyphosphoryloxymethyl-1',3'-oxathiolane (389128-32-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 99 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h

2.2: 80 percent / tetrahydrofuran / -78 - 20 °C

With lithium aluminium tetrahydride; n-butyllithium; In tetrahydrofuran; hexane;

DOI:10.1016/S0040-4020(01)00800-6

upstream raw materials:

4-azidobutan-1-amine

5'(S)-[O⁴-(2,4,6-triisopropylbenzenesulfonyl)uracil-1-yl]-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester

5'(S)-(uracil-1-yl)-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester

Downstream raw materials:

5'(S)-{N⁴-[1-(4-azidobutyl)]cytosin-1-yl}-2'(R)-dibenzyl-oxyphosphoryloxymethyl-1',3'-oxathiolane