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

Base Information

• Chemical Name: 5'(S)-{N⁴-[1-(4-azidobutyl)]cytosin-1-yl}-2'(R)-dibenzyl-oxyphosphoryloxymethyl-1',3'-oxathiolane
• CAS No.: 389128-32-9
• Molecular Formula: C₂₆H₃₁N₆O₆PS
• Molecular Weight: 586.609

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

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

Chemical Property:

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

There total 4 articles about 5'(S)-{N⁴-[1-(4-azidobutyl)]cytosin-1-yl}-2'(R)-dibenzyl-oxyphosphoryloxymethyl-1',3'-oxathiolane 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: 80.0%

dibenzyl phosphochloridate (538-37-4) + 5'(S)-{N4-[1-(4-azidobutyl)]cytosin-1-yl}-2'(R)-hydroxymethyl-1',3'-oxathiolane (389128-31-8) → 5'(S)-{N4-[1-(4-azidobutyl)]cytosin-1-yl}-2'(R)-dibenzyl-oxyphosphoryloxymethyl-1',3'-oxathiolane (389128-32-9)

Guidance literature:

5'(S)-{N⁴-[1-(4-azidobutyl)]cytosin-1-yl}-2'(R)-hydroxymethyl-1',3'-oxathiolane; With n-butyllithium; In tetrahydrofuran; hexane; for 0.5h;

dibenzyl phosphochloridate; In tetrahydrofuran; at -78 - 20 ℃;

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

Guidance literature:

Multi-step reaction with 4 steps

1.1: 99 percent / 4-DMAP; Et₃N / CH₂Cl₂ / 12 h / 20 °C

2.1: 76 percent / CH₂Cl₂ / 0.75 h / 0 °C

3.1: 99 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / 0 °C

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

4.2: 80 percent / tetrahydrofuran / -78 - 20 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; triethylamine; In tetrahydrofuran; hexane; 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:

dibenzyl phosphochloridate

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

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

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

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