3-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-methylene-tetrahydro-furan-3-yl]-3H-purin-6-ylamine

Base Information

• Chemical Name: 3-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-methylene-tetrahydro-furan-3-yl]-3H-purin-6-ylamine
• CAS No.: 292864-79-0
• Molecular Formula: C₂₇H₃₁N₅O₂Si
• Molecular Weight: 485.661

Synonyms:3-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-methylene-tetrahydro-furan-3-yl]-3H-purin-6-ylamine

Chemical Property of 3-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-methylene-tetrahydro-furan-3-yl]-3H-purin-6-ylamine

Chemical Property:

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Technology Process of 3-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-methylene-tetrahydro-furan-3-yl]-3H-purin-6-ylamine

There total 6 articles about 3-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-methylene-tetrahydro-furan-3-yl]-3H-purin-6-ylamine 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: 42.0%

adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) + (3R,5S)-5-{{[(tert-butyl)diphenylsilyl]oxy}methyl}tetrahdyro-4-methylidenefuran-3-ol (292864-77-8) → 9-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-methylene-tetrahydro-furan-3-yl]-9H-purin-6-ylamine (292864-78-9) + 3-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-methylene-tetrahydro-furan-3-yl]-3H-purin-6-ylamine (292864-79-0)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; at 20 ℃; for 22h;

DOI:10.1002/1522-2675(20000705)83:7<1398::AID-HLCA1398>3.0.CO;2-I

Reference yield:

1,2-O-isopropylidene-5-O-(triphenylmethyl)-α-D-erythro-pentofuranos-3-ulose (20590-54-9) → 3-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-methylene-tetrahydro-furan-3-yl]-3H-purin-6-ylamine (292864-79-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / NaH / dimethylsulfoxide / 0.5 h / 20 °C

2: 78 percent / HCl; water / methanol; dioxane / 2 h / Heating

3: 78 percent / Me₃SiCl; hexamethyldisilazane / 17 h / Heating

4: 84 percent / pyridine

5: 19 percent / Ph₃P; DEAD / dioxane / 22 h / 20 °C

With pyridine; hydrogenchloride; chloro-trimethyl-silane; water; sodium hydride; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; diethylazodicarboxylate; In 1,4-dioxane; methanol; dimethyl sulfoxide; 1: Condensation / 2: Hydrolysis / 3: demethoxylation / 4: silylation / 5: Substitution;

DOI:10.1002/1522-2675(20000705)83:7<1398::AID-HLCA1398>3.0.CO;2-I

Reference yield:

1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose (20590-53-8) → 3-[5-(tert-butyl-diphenyl-silanyloxymethyl)-4-methylene-tetrahydro-furan-3-yl]-3H-purin-6-ylamine (292864-79-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 67 percent / P₂O₅ / dimethylsulfoxide / 20 h / 30 °C

2: 89 percent / NaH / dimethylsulfoxide / 0.5 h / 20 °C

3: 78 percent / HCl; water / methanol; dioxane / 2 h / Heating

4: 78 percent / Me₃SiCl; hexamethyldisilazane / 17 h / Heating

5: 84 percent / pyridine

6: 19 percent / Ph₃P; DEAD / dioxane / 22 h / 20 °C

With pyridine; hydrogenchloride; chloro-trimethyl-silane; water; phosphorus pentoxide; sodium hydride; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; diethylazodicarboxylate; In 1,4-dioxane; methanol; dimethyl sulfoxide; 1: Oxidation / 2: Condensation / 3: Hydrolysis / 4: demethoxylation / 5: silylation / 6: Substitution;

DOI:10.1002/1522-2675(20000705)83:7<1398::AID-HLCA1398>3.0.CO;2-I

upstream raw materials:

adenine

(3R,5S)-5-{{[(tert-butyl)diphenylsilyl]oxy}methyl}tetrahdyro-4-methylidenefuran-3-ol

1,2-O-isopropylidene-5-O-(triphenylmethyl)-α-D-erythro-pentofuranos-3-ulose

1,2-O-isopropylidene-5-O-trityl-α-D-xylofuranose

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