(1'S,2'R,3'S,4'R,5'S)-4-(6-amino-9H-purin-9-yl)-1-[(phenylmethoxy)methyl]bicyclo[3.1.0]hexane-2,3-(O-isopropylidene)

Base Information

• Chemical Name: (1'S,2'R,3'S,4'R,5'S)-4-(6-amino-9H-purin-9-yl)-1-[(phenylmethoxy)methyl]bicyclo[3.1.0]hexane-2,3-(O-isopropylidene)
• CAS No.: 174498-03-4
• Molecular Formula: C₂₂H₂₅N₅O₃
• Molecular Weight: 407.472
• Mol file: 174498-03-4.mol

Synonyms:(1'S,2'R,3'S,4'R,5'S)-4-(6-amino-9H-purin-9-yl)-1-[(phenylmethoxy)methyl]bicyclo[3.1.0]hexane-2,3-(O-isopropylidene)

Chemical Property of (1'S,2'R,3'S,4'R,5'S)-4-(6-amino-9H-purin-9-yl)-1-[(phenylmethoxy)methyl]bicyclo[3.1.0]hexane-2,3-(O-isopropylidene)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'S,2'R,3'S,4'R,5'S)-4-(6-amino-9H-purin-9-yl)-1-[(phenylmethoxy)methyl]bicyclo[3.1.0]hexane-2,3-(O-isopropylidene)

There total 4 articles about (1'S,2'R,3'S,4'R,5'S)-4-(6-amino-9H-purin-9-yl)-1-[(phenylmethoxy)methyl]bicyclo[3.1.0]hexane-2,3-(O-isopropylidene) 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: 95.0%

(1'R,2'R,3'S,4'R,5'S)-4-(chloropurin-9-yl)-1-[(phenylmethoxy)methyl]-bicyclo[3.1.0]hexane-2,3-(O-isopropylidene) (328396-54-9) → (1'S,2'R,3'S,4'R,5'S)-4-(6-amino-9H-purin-9-yl)-1-[(phenylmethoxy)methyl]bicyclo[3.1.0]hexane-2,3-(O-isopropylidene) (174498-03-4)

Guidance literature:

With ammonia; In isopropyl alcohol; at 90 ℃; for 15h;

DOI:10.1021/jm010369e DOI:10.1021/jm010538v

Reference yield: 68.0%

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) + Methanesulfonic acid (1aR,1bR,4aR,5S,5aS)-1a-benzyloxymethyl-3,3-dimethyl-hexahydro-2,4-dioxa-cyclopropa[a]pentalen-5-yl ester (174498-02-3) → 7-((1aR,1bR,4aS,5R,5aS)-1a-Benzyloxymethyl-3,3-dimethyl-hexahydro-2,4-dioxa-cyclopropa[a]pentalen-5-yl)-7H-purin-6-ylamine + (1'S,2'R,3'S,4'R,5'S)-4-(6-amino-9H-purin-9-yl)-1-[(phenylmethoxy)methyl]bicyclo[3.1.0]hexane-2,3-(O-isopropylidene) (174498-03-4)

Guidance literature:

With 18-crown-6 ether; potassium carbonate; In N,N-dimethyl-formamide; at 100 ℃; for 18h;

Reference yield:

(1S,4R,5S)-(-)-3-<(benzyloxy)methyl>-4,5-O-isopropylidene-2-cyclopenten-1-ol (89291-76-9) → (1'S,2'R,3'S,4'R,5'S)-4-(6-amino-9H-purin-9-yl)-1-[(phenylmethoxy)methyl]bicyclo[3.1.0]hexane-2,3-(O-isopropylidene) (174498-03-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / Et₂Zn / CH₂Cl₂ / 15 h / 0 deg C to room temp.

2: 100 percent / pyridine / 4 h / 0 °C

3: 68 percent / K₂CO₃, 18-crown-6 / dimethylformamide / 18 h / 100 °C

With pyridine; 18-crown-6 ether; diethylzinc; potassium carbonate; In dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

adenine

Methanesulfonic acid (1aR,1bR,4aR,5S,5aS)-1a-benzyloxymethyl-3,3-dimethyl-hexahydro-2,4-dioxa-cyclopropa[a]pentalen-5-yl ester

(1'R,2'R,3'S,4'R,5'S)-4-(chloropurin-9-yl)-1-[(phenylmethoxy)methyl]-bicyclo[3.1.0]hexane-2,3-(O-isopropylidene)

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