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

Base Information

• Chemical Name: 5'(S)-[O⁴-(2,4,6-triisopropylbenzenesulfonyl)uracil-1-yl]-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester
• CAS No.: 389128-29-4
• Molecular Formula: C₃₃H₄₈N₂O₇S₂
• Molecular Weight: 648.885

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

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

Chemical Property:

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

There total 1 articles about 5'(S)-[O⁴-(2,4,6-triisopropylbenzenesulfonyl)uracil-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: 99.0%

2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4) + 5'(S)-(uracil-1-yl)-1',3'-oxathiolane-2'(R)-carboxylic acid (1R,2S,5R)-menthyl ester (389128-28-3) → 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)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 12h;

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

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)-[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}-2'(R)-dibenzyl-oxyphosphoryloxymethyl-1',3'-oxathiolane (389128-32-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 76 percent / CH₂Cl₂ / 0.75 h / 0 °C

2.1: 99 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

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

3.2: 80 percent / tetrahydrofuran / -78 - 20 °C

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

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

upstream raw materials:

2,4,6-triisopropylphenylsulfonyl chloride

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

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

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