9-[(3aS,4S,6aR)-5-Fluoro-3a,6a-dihydro-2,2-dimethyl-6-[(phenylmethoxy)methyl]-4H-cyclopenta-1,3-dioxol-4-yl]-9H-purin-6-amine

Base Information

• Chemical Name: 9-[(3aS,4S,6aR)-5-Fluoro-3a,6a-dihydro-2,2-dimethyl-6-[(phenylmethoxy)methyl]-4H-cyclopenta-1,3-dioxol-4-yl]-9H-purin-6-amine
• CAS No.: 491578-04-2
• Molecular Formula: C₂₁H₂₂FN₅O₃
• Molecular Weight: 411.436
• DSSTox Substance ID: DTXSID901103864
• Mol file: 491578-04-2.mol

Synonyms:DTXSID901103864;491578-04-2;9-[(3aS,4S,6aR)-5-Fluoro-3a,6a-dihydro-2,2-dimethyl-6-[(phenylmethoxy)methyl]-4H-cyclopenta-1,3-dioxol-4-yl]-9H-purin-6-amine

Chemical Property of 9-[(3aS,4S,6aR)-5-Fluoro-3a,6a-dihydro-2,2-dimethyl-6-[(phenylmethoxy)methyl]-4H-cyclopenta-1,3-dioxol-4-yl]-9H-purin-6-amine

Chemical Property:

• XLogP3: 0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 411.17066774
• Heavy Atom Count: 30
• Complexity: 671

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(OC2C(C(=C(C2O1)COCC3=CC=CC=C3)F)N4C=NC5=C(N=CN=C54)N)C
• Isomeric SMILES: CC1(O[C@H]2[C@@H](C(=C([C@H]2O1)COCC3=CC=CC=C3)F)N4C=NC5=C(N=CN=C54)N)C

Technology Process of 9-[(3aS,4S,6aR)-5-Fluoro-3a,6a-dihydro-2,2-dimethyl-6-[(phenylmethoxy)methyl]-4H-cyclopenta-1,3-dioxol-4-yl]-9H-purin-6-amine

There total 6 articles about 9-[(3aS,4S,6aR)-5-Fluoro-3a,6a-dihydro-2,2-dimethyl-6-[(phenylmethoxy)methyl]-4H-cyclopenta-1,3-dioxol-4-yl]-9H-purin-6-amine 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: 69.0%

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) + (3aR,4R,6aR)-methanesulfonic acid 6-benzyloxymethyl-5-fluoro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl ester (1053696-34-6) → (3aS,4S,6aR)-9-(6-benzyloxymethyl-5-fluoro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-9H-purin-6-ylamine (491578-04-2)

Guidance literature:

With 18-crown-6 ether; potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃;

DOI:10.1021/jm025557z

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) → (3aS,4S,6aR)-9-(6-benzyloxymethyl-5-fluoro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-9H-purin-6-ylamine (491578-04-2)

Guidance literature:

Multi-step reaction with 7 steps

1: I₂; pyridine / CCl₄

2: NaBH₄; CeCl₃*7H₂O

3: 97 percent / dimethylformamide / 50 °C

4: 97 percent / n-BuLi; (PhSO₂)2NF / -78 °C

5: nBu₄NF / tetrahydrofuran

6: Et₃N

7: 18-crown-6 / dimethylformamide

With pyridine; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; 18-crown-6 ether; tetrabutyl ammonium fluoride; iodine; N-fluorobis(benzenesulfon)imide; triethylamine; In tetrahydrofuran; tetrachloromethane; N,N-dimethyl-formamide;

DOI:10.1081/NCN-120021961

Reference yield:

(3aS,4R,6aR)-6-(benzyloxymethyl)-5-fluoro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (491578-02-0) → (3aS,4S,6aR)-9-(6-benzyloxymethyl-5-fluoro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-9H-purin-6-ylamine (491578-04-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N

2: 18-crown-6 / dimethylformamide

With 18-crown-6 ether; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1081/NCN-120021961

upstream raw materials:

adenine

(3aR,4R,6aR)-methanesulfonic acid 6-benzyloxymethyl-5-fluoro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl ester

(3aR,6aR)-6-Benzyloxymethyl-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-one

(3aS,4R,6aR)-6-(benzyloxymethyl)-5-fluoro-2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol