Toluene-4-sulfonic acid (3aR,4R,6R,6aS)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (3aR,4R,6R,6aS)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl ester
CAS No.:173346-41-3
Molecular Formula:C₂₁H₂₅N₅O₅S
Molecular Weight:459.526
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (3aR,4R,6R,6aS)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl ester

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Chemical Property of Toluene-4-sulfonic acid (3aR,4R,6R,6aS)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl ester

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Technology Process of Toluene-4-sulfonic acid (3aR,4R,6R,6aS)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl ester

There total 11 articles about Toluene-4-sulfonic acid (3aR,4R,6R,6aS)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl 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: 80.0%

: 174171-97-2
(1'R,2'R,3'S,4'R)-4'-(6-aminopurin-9-yl)-1'-hydroxymethyl-2',3'-O-isopropylidenecyclopentane-2',3'-diol

: 98-59-9
p-toluenesulfonyl chloride

: 173346-41-3
Toluene-4-sulfonic acid (3aR,4R,6R,6aS)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl ester

Guidance literature:: With pyridine; at -20 ℃; for 2h;

Reference yield:

: 67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1
2,3-O-isopropylidene-D-ribofuranose

: 173346-41-3
Toluene-4-sulfonic acid (3aR,4R,6R,6aS)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: Ph₃P; I₂; imidazole

1.2: Zn / methanol

2.1: 80 percent / CH₂Cl₂; tetrahydrofuran / 3 h / -40 - 0 °C

3.1: Grubbs catalyst / CH₂Cl₂

4.1: PCC / CH₂Cl₂

5.1: 80 percent / CuBr*Me₂S; TMSCl; HMPA / tetrahydrofuran / -78 - 0 °C

6.1: 98 percent / LiAlH₄ / tetrahydrofuran / 3 h / 20 °C

7.1: DIAD; Ph₃P / tetrahydrofuran / 0 - 20 °C

8.1: NaIO₄; OsO₄ / methanol; H₂O / 3 h / 0 - 20 °C

9.1: 2.09 g / NaBH₄ / methanol / 1 h / 0 °C

10.1: 91 percent / NH₃ / methanol / 24 h / 100 °C

11.1: pyridine / 72 h / -20 °C

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; di-isopropyl azodicarboxylate; ammonia; iodine; triphenylphosphine; pyridinium chlorochromate; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; water; 7.1: Mitsunobu reaction;

Reference yield:

: 155934-55-7
(4R,5R)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde

: 173346-41-3
Toluene-4-sulfonic acid (3aR,4R,6R,6aS)-6-(6-amino-purin-9-yl)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 80 percent / CH₂Cl₂; tetrahydrofuran / 3 h / -40 - 0 °C

2: Grubbs catalyst / CH₂Cl₂

3: PCC / CH₂Cl₂

4: 80 percent / CuBr*Me₂S; TMSCl; HMPA / tetrahydrofuran / -78 - 0 °C

5: 98 percent / LiAlH₄ / tetrahydrofuran / 3 h / 20 °C

6: DIAD; Ph₃P / tetrahydrofuran / 0 - 20 °C

7: NaIO₄; OsO₄ / methanol; H₂O / 3 h / 0 - 20 °C

8: 2.09 g / NaBH₄ / methanol / 1 h / 0 °C

9: 91 percent / NH₃ / methanol / 24 h / 100 °C

10: pyridine / 72 h / -20 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; chloro-trimethyl-silane; copper(I) bromide dimethylsulfide complex; di-isopropyl azodicarboxylate; ammonia; triphenylphosphine; pyridinium chlorochromate; Grubbs catalyst first generation; In tetrahydrofuran; methanol; dichloromethane; water; 6: Mitsunobu reaction;