11-{(2R,3R,4R,5R)-5-[6-(Trityl-amino)-purin-9-yl]-4-trityloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy}-undecan-1-ol

Base Information

• Chemical Name: 11-{(2R,3R,4R,5R)-5-[6-(Trityl-amino)-purin-9-yl]-4-trityloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy}-undecan-1-ol
• CAS No.: 191853-39-1
• Molecular Formula: C₇₈H₇₇N₅O₅
• Molecular Weight: 1164.5

Synonyms:11-{(2R,3R,4R,5R)-5-[6-(Trityl-amino)-purin-9-yl]-4-trityloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy}-undecan-1-ol

Chemical Property of 11-{(2R,3R,4R,5R)-5-[6-(Trityl-amino)-purin-9-yl]-4-trityloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy}-undecan-1-ol

Chemical Property:

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Technology Process of 11-{(2R,3R,4R,5R)-5-[6-(Trityl-amino)-purin-9-yl]-4-trityloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy}-undecan-1-ol

There total 3 articles about 11-{(2R,3R,4R,5R)-5-[6-(Trityl-amino)-purin-9-yl]-4-trityloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy}-undecan-1-ol 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: 94.0%

[9-((2R,3R,4R,5R)-4-{11-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-undecyloxy}-3-trityloxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-trityl-amine (191853-36-8) → 11-{(2R,3R,4R,5R)-5-[6-(Trityl-amino)-purin-9-yl]-4-trityloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy}-undecan-1-ol (191853-39-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;

DOI:10.1002/hlca.19970800313

Reference yield:

1-Bromo-11-hydroxyundecane (1611-56-9) → 11-{(2R,3R,4R,5R)-5-[6-(Trityl-amino)-purin-9-yl]-4-trityloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy}-undecan-1-ol (191853-39-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / 1H-imidazole / tetrahydrofuran

2: 88 percent / 1.) NaH; 2.) NaI / acetonitrile / 1.) room temp., 20 min.; 2.) room temp. overnight

3: 94 percent / Bu₄NF*3H₂O / tetrahydrofuran / Ambient temperature

With 1H-imidazole; tetrabutyl ammonium fluoride; sodium hydride; sodium iodide; In tetrahydrofuran; acetonitrile;

DOI:10.1002/hlca.19970800313

Reference yield:

(11-bromoundecyloxy)dimethyl(1,1,2-trimethylpropyl)silane (191853-33-5) → 11-{(2R,3R,4R,5R)-5-[6-(Trityl-amino)-purin-9-yl]-4-trityloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy}-undecan-1-ol (191853-39-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / 1.) NaH; 2.) NaI / acetonitrile / 1.) room temp., 20 min.; 2.) room temp. overnight

2: 94 percent / Bu₄NF*3H₂O / tetrahydrofuran / Ambient temperature

With tetrabutyl ammonium fluoride; sodium hydride; sodium iodide; In tetrahydrofuran; acetonitrile;

DOI:10.1002/hlca.19970800313

upstream raw materials:

[9-((2R,3R,4R,5R)-4-{11-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-undecyloxy}-3-trityloxy-5-trityloxymethyl-tetrahydro-furan-2-yl)-9H-purin-6-yl]-trityl-amine

1-Bromo-11-hydroxyundecane

(11-bromoundecyloxy)dimethyl(1,1,2-trimethylpropyl)silane

Downstream raw materials:

4-Oxo-pentanoic acid 11-{(2R,3R,4R,5R)-5-[6-(trityl-amino)-purin-9-yl]-4-trityloxy-2-trityloxymethyl-tetrahydro-furan-3-yloxy}-undecyl ester

4-Oxo-pentanoic acid 11-{(2R,3R,4R,5R)-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-5-{6-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-4-[2-(4-nitro-phenyl)-ethoxycarbonyloxy]-tetrahydro-furan-3-yloxy}-undecyl ester

4-Oxo-pentanoic acid 11-((2R,3S,4R,5R)-4-hydroxy-2-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-5-{6-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-tetrahydro-furan-3-yloxy)-undecyl ester

4-Oxo-pentanoic acid 11-{(2R,3R,4R,5R)-2-hydroxymethyl-5-{6-[2-(4-nitro-phenyl)-ethoxycarbonylamino]-purin-9-yl}-4-[2-(4-nitro-phenyl)-ethoxycarbonyloxy]-tetrahydro-furan-3-yloxy}-undecyl ester

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