(1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enylphenoxythiocarboxylate

Base Information

Chemical Name:(1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enylphenoxythiocarboxylate
CAS No.:133119-18-3
Molecular Formula:C₂₅H₂₄N₆O₃S
Molecular Weight:488.57
Hs Code.:

Synonyms:(1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enylphenoxythiocarboxylate

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Chemical Property of (1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enylphenoxythiocarboxylate

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Technology Process of (1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enylphenoxythiocarboxylate

There total 5 articles about (1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enylphenoxythiocarboxylate 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: 92.0%

: 133119-17-2
(1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enol

: 1005-56-7
phenylcarbonochloridothioate

: 133119-18-3
(1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enylphenoxythiocarboxylate

Guidance literature:: With dmap; In dichloromethane; 1) -20 deg C, 1 h, 2) -15 deg C, 0.75 h;
DOI:10.1039/P19910002479

Reference yield:

: 133119-16-1
(1S,2S,5R)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hex-3-ene

: 133119-18-3
(1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enylphenoxythiocarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 1) NaH, 2) 15-crown-5 / 1) DMF, 85 deg C, 20 min, 2) DMF, 100 deg C, 3 h

2: 92 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 1) -20 deg C, 1 h, 2) -15 deg C, 0.75 h

With dmap; 15-crown-5; sodium hydride; In dichloromethane;
DOI:10.1039/P19910002479

Reference yield:

: 117641-39-1
(2R,3S)-2-benzyloxymethyl-6-oxabicyclo<3.1.0>hexan-3-ol

: 133119-18-3
(1S,2S,5S)-5-benzyloxymethyl-2-(2,6-diamino-9H-purin-9-yl)cyclopent-3-enylphenoxythiocarboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 81 percent / 4-dimethylaminopyridine, Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

2: Bu₄NF / tetrahydrofuran / 72 h / Ambient temperature

3: 1) NaH, 2) 15-crown-5 / 1) DMF, 85 deg C, 20 min, 2) DMF, 100 deg C, 3 h

4: 92 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 1) -20 deg C, 1 h, 2) -15 deg C, 0.75 h

With dmap; 15-crown-5; tetrabutyl ammonium fluoride; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1039/P19910002479