(1'S,2'R,3'S,4'R)-2',3'-(isopropylidenedioxy)-4'-methyl-4'-(6-chloro-9H-purin-9-yl)-2'-cyclopenten-1-yl benzoate

Base Information

Chemical Name:(1'S,2'R,3'S,4'R)-2',3'-(isopropylidenedioxy)-4'-methyl-4'-(6-chloro-9H-purin-9-yl)-2'-cyclopenten-1-yl benzoate
CAS No.:639467-39-3
Molecular Formula:C₂₁H₂₁ClN₄O₄
Molecular Weight:428.875
Hs Code.:

Synonyms:(1'S,2'R,3'S,4'R)-2',3'-(isopropylidenedioxy)-4'-methyl-4'-(6-chloro-9H-purin-9-yl)-2'-cyclopenten-1-yl benzoate

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Chemical Property of (1'S,2'R,3'S,4'R)-2',3'-(isopropylidenedioxy)-4'-methyl-4'-(6-chloro-9H-purin-9-yl)-2'-cyclopenten-1-yl benzoate

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Technology Process of (1'S,2'R,3'S,4'R)-2',3'-(isopropylidenedioxy)-4'-methyl-4'-(6-chloro-9H-purin-9-yl)-2'-cyclopenten-1-yl benzoate

There total 8 articles about (1'S,2'R,3'S,4'R)-2',3'-(isopropylidenedioxy)-4'-methyl-4'-(6-chloro-9H-purin-9-yl)-2'-cyclopenten-1-yl benzoate 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: 81.1%

: 639467-38-2
(1'S,2'R,3'S,4'R)-2',3'-dihydroxy-4'-methyl-4'-(6-chloro-9H-purin-9-yl)-2'-cyclopenten-1-yl benzoate

: 149-73-5
trimethyl orthoformate

: 639467-39-3
(1'S,2'R,3'S,4'R)-2',3'-(isopropylidenedioxy)-4'-methyl-4'-(6-chloro-9H-purin-9-yl)-2'-cyclopenten-1-yl benzoate

Guidance literature:: With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 12h;
DOI:10.1021/jo030238g

Reference yield:

: 61305-35-9
(R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone

: 639467-39-3
(1'S,2'R,3'S,4'R)-2',3'-(isopropylidenedioxy)-4'-methyl-4'-(6-chloro-9H-purin-9-yl)-2'-cyclopenten-1-yl benzoate

Guidance literature:: Multi-step reaction with 6 steps

1: 60 percent / diethyl ether / 3 h / -40 °C

2: 30 percent / Ph₃P; diisopropylazodicarboxylate / tetrahydrofuran / 24 h / 20 °C

3: 71 percent / K-10 clay / ethyl acetate; methanol; H₂O / 8 h / 75 °C

4: 67 percent / Ph₃P; diisopropylazodicarboxylate / tetrahydrofuran / 2 h / 20 °C

5: 82.3 percent / aq. N-methylmorpholine N-oxide; OsO₄ / tetrahydrofuran; H₂O / 24 h / 20 °C

6: 81.1 percent / p-TsOH / acetone / 12 h / 20 °C

With osmium(VIII) oxide; di-isopropyl azodicarboxylate; K-10 clay; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; water; ethyl acetate; acetone; 2: Mitsunobu reaction / 4: Mitsunobu reaction;
DOI:10.1021/jo030238g

Reference yield:

: 104069-09-2
(1S,4R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enol

: 639467-39-3
(1'S,2'R,3'S,4'R)-2',3'-(isopropylidenedioxy)-4'-methyl-4'-(6-chloro-9H-purin-9-yl)-2'-cyclopenten-1-yl benzoate

Guidance literature:: Multi-step reaction with 7 steps

1: 84.13 percent / pyridinium chlorochromate / CH₂Cl₂ / 14 h

2: 60 percent / diethyl ether / 3 h / -40 °C

3: 30 percent / Ph₃P; diisopropylazodicarboxylate / tetrahydrofuran / 24 h / 20 °C

4: 71 percent / K-10 clay / ethyl acetate; methanol; H₂O / 8 h / 75 °C

5: 67 percent / Ph₃P; diisopropylazodicarboxylate / tetrahydrofuran / 2 h / 20 °C

6: 82.3 percent / aq. N-methylmorpholine N-oxide; OsO₄ / tetrahydrofuran; H₂O / 24 h / 20 °C

7: 81.1 percent / p-TsOH / acetone / 12 h / 20 °C

With osmium(VIII) oxide; di-isopropyl azodicarboxylate; K-10 clay; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triphenylphosphine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; acetone; 3: Mitsunobu reaction / 5: Mitsunobu reaction;
DOI:10.1021/jo030238g