(-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>-6-chloropurine

Base Information

• Chemical Name: (-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>-6-chloropurine
• CAS No.: 89291-81-6
• Molecular Formula: C₂₁H₂₁ClN₄O₃
• Molecular Weight: 412.876
• Mol file: 89291-81-6.mol

Synonyms:(-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>-6-chloropurine

Chemical Property of (-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>-6-chloropurine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>-6-chloropurine

There total 24 articles about (-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>-6-chloropurine 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: 31.0%

sodium salt of 6-chloropurine (73349-28-7) + (1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol p-toluenesulfonate (100806-47-1) → (-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>-6-chloropurine (89291-81-6)

Guidance literature:

In acetonitrile; at 90 ℃; for 3h;

DOI:10.1016/S0040-4039(00)89219-9

Reference yield:

2,3-O-isopropylidene-D-ribonic-γ-lactone (30725-00-9) → (-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>-6-chloropurine (89291-81-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C

1.2: 78 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 92 percent / sodium hydride / dimethylformamide / 0.5 h / 0 °C

3.1: 77 percent / potassium hydroxide / methanol / 20 h / 20 °C

4.1: 80 percent / pyridine; chromium trioxide / CH₂Cl₂ / 20 °C

5.1: potassium carbonate; 18-crown-6 ether / benzene / 0.67 h / 56 °C

6.1: cerium(III) chloride heptahydrate; sodium borohydride / methanol / 0.25 h

7.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 20 °C

With pyridine; chromium(VI) oxide; potassium hydroxide; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; 18-crown-6 ether; sodium hydride; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; benzene; 1.1: Metallation / 1.2: Addition / 2.1: Etherification / 3.1: Hydrolysis / 4.1: Oxidation / 5.1: Cyclization / 6.1: Reduction / 7.1: Substitution;

DOI:10.1016/S0040-4020(00)00379-3

Reference yield:

(3aR,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-one (117307-62-7,89291-75-8) → (-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>-6-chloropurine (89291-81-6)

Guidance literature:

Multi-step reaction with 2 steps

1: cerium(III) chloride heptahydrate; sodium borohydride / methanol / 0.25 h

2: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 20 °C

With sodium tetrahydroborate; cerium(III) chloride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; 1: Reduction / 2: Substitution;

DOI:10.1016/S0040-4020(00)00379-3

upstream raw materials:

sodium salt of 6-chloropurine

(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol p-toluenesulfonate

(1R,4R,5S)-(-)-1-<(5-amino-6-chloropyrimidinyl)amino>-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopentene

orthoformic acid triethyl ester

Downstream raw materials:

(-)-9-<(1R,4R,5S)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-yl>adenine

(-)-9-[(1R,4R,5S)-3-(benzyloxy)methyl-4,5-dihydroxycyclopent-2-en-1-yl]-6-chloropurine

(1R,2S,3S,4S,5R)-(-)-1-benzyloxymethyl-4-(6-chloropurin-9-yl)-6-oxa-bicyclo[3.1.0]hexane-2,3-diol

(1S,2S,3S,4S,5S)-(-)-1-benzyloxymethyl-4-(6-chloropurin-9-yl)-6-oxa-bicyclo[3.1.0]hexane-2,3-diol