N²-isobutyryl-2’,3’-O-isopropylidene-8-{[ (methylsulfonyl)oxy]methyl}-5’-S-[(4-methoxyphenyl)diphenylmethyl]-O⁶-[2-(4-nitrophenyl)ethyl]-5’-thioguanosine

Base Information

• Chemical Name: N²-isobutyryl-2’,3’-O-isopropylidene-8-{[ (methylsulfonyl)oxy]methyl}-5’-S-[(4-methoxyphenyl)diphenylmethyl]-O⁶-[2-(4-nitrophenyl)ethyl]-5’-thioguanosine
• CAS No.: 1449295-01-5
• Molecular Formula: C₄₇H₅₀N₆O₁₁S₂
• Molecular Weight: 939.08

Synonyms:N²-isobutyryl-2’,3’-O-isopropylidene-8-{[ (methylsulfonyl)oxy]methyl}-5’-S-[(4-methoxyphenyl)diphenylmethyl]-O⁶-[2-(4-nitrophenyl)ethyl]-5’-thioguanosine

Chemical Property of N²-isobutyryl-2’,3’-O-isopropylidene-8-{[ (methylsulfonyl)oxy]methyl}-5’-S-[(4-methoxyphenyl)diphenylmethyl]-O⁶-[2-(4-nitrophenyl)ethyl]-5’-thioguanosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N²-isobutyryl-2’,3’-O-isopropylidene-8-{[ (methylsulfonyl)oxy]methyl}-5’-S-[(4-methoxyphenyl)diphenylmethyl]-O⁶-[2-(4-nitrophenyl)ethyl]-5’-thioguanosine

There total 9 articles about N²-isobutyryl-2’,3’-O-isopropylidene-8-{[ (methylsulfonyl)oxy]methyl}-5’-S-[(4-methoxyphenyl)diphenylmethyl]-O⁶-[2-(4-nitrophenyl)ethyl]-5’-thioguanosine 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%

8-(hydroxymethyl)-N2-isobutyryl-2’,3’-O-isopropylidene-5’-S-[(4-methoxyphenyl)diphenylmethyl]-O6-[2-(4-nitrophenyl)ethyl]-5’-thioguanosine (1449295-00-4) + methanesulfonyl chloride (124-63-0) → N2-isobutyryl-2’,3’-O-isopropylidene-8-{[ (methylsulfonyl)oxy]methyl}-5’-S-[(4-methoxyphenyl)diphenylmethyl]-O6-[2-(4-nitrophenyl)ethyl]-5’-thioguanosine (1449295-01-5)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.75h;

DOI:10.1002/hlca.201300043

Reference yield:

2',3'-isopropylideneguanosine (362-76-5) → N2-isobutyryl-2’,3’-O-isopropylidene-8-{[ (methylsulfonyl)oxy]methyl}-5’-S-[(4-methoxyphenyl)diphenylmethyl]-O6-[2-(4-nitrophenyl)ethyl]-5’-thioguanosine (1449295-01-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: pyridine; chloro-trimethyl-silane / dichloromethane / 6 h / 0 °C

1.2: 16.17 h / 0 - 20 °C

1.3: 12 h

2.1: methyltriphenoxyphosphonium iodide / acetonitrile / 1 h

3.1: sodium hydride / mineral oil; tetrahydrofuran / 0.08 h / 0 °C

3.2: 1.58 h / 0 - 20 °C

4.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 1 h / -78 - -68 °C

4.2: 1.17 h / 0 °C

5.1: sodium tetrahydroborate / ethanol / 0.5 h

6.1: 1,4-dioxane / 2 h

7.1: triphenylphosphine; di-isopropyl azodicarboxylate / 1,4-dioxane / 4 h

8.1: ammonium fluoride / methanol / 2 h

9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.75 h / 0 °C

With pyridine; ammonium fluoride; sodium tetrahydroborate; chloro-trimethyl-silane; di-isopropyl azodicarboxylate; methyltriphenoxyphosphonium iodide; sodium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; acetonitrile; mineral oil; 7.1: |Mitsunobu Displacement;

DOI:10.1002/hlca.201300043

Reference yield:

N2-isobutyryl-2’,3’-O-isopropylideneguanosine (132840-60-9) → N2-isobutyryl-2’,3’-O-isopropylidene-8-{[ (methylsulfonyl)oxy]methyl}-5’-S-[(4-methoxyphenyl)diphenylmethyl]-O6-[2-(4-nitrophenyl)ethyl]-5’-thioguanosine (1449295-01-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: methyltriphenoxyphosphonium iodide / acetonitrile / 1 h

2.1: sodium hydride / mineral oil; tetrahydrofuran / 0.08 h / 0 °C

2.2: 1.58 h / 0 - 20 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 1 h / -78 - -68 °C

3.2: 1.17 h / 0 °C

4.1: sodium tetrahydroborate / ethanol / 0.5 h

5.1: 1,4-dioxane / 2 h

6.1: triphenylphosphine; di-isopropyl azodicarboxylate / 1,4-dioxane / 4 h

7.1: ammonium fluoride / methanol / 2 h

8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.75 h / 0 °C

With ammonium fluoride; sodium tetrahydroborate; di-isopropyl azodicarboxylate; methyltriphenoxyphosphonium iodide; sodium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; acetonitrile; mineral oil; 6.1: |Mitsunobu Displacement;

DOI:10.1002/hlca.201300043

upstream raw materials:

8-(hydroxymethyl)-N2-isobutyryl-2’,3’-O-isopropylidene-5’-S-[(4-methoxyphenyl)diphenylmethyl]-O6-[2-(4-nitrophenyl)ethyl]-5’-thioguanosine

methanesulfonyl chloride

2',3'-isopropylideneguanosine

N²-isobutyryl-2’,3’-O-isopropylideneguanosine

Downstream raw materials:

N²-isobutyryl-2’,3’-O-isopropylidene-5’-S-[(4-methoxyphenyl)diphenylmethyl]-O⁶-[2-(4-nitrophenyl)-ethyl]-5’-thioguanosine-8-methyl-(8¹→5’-S)-N⁴-benzoyl-2’,3’-O-isopropylidene-6-{[(4-methoxyphenyl)-diphenylmethoxy]methyl}-5’-thiocytidine

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