9-[(1R,2R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)bicyclo[3.1.0] hex-3-en-2-yl]-6-chloro-9H-purin-2-amine

Base Information

• Chemical Name: 9-[(1R,2R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)bicyclo[3.1.0] hex-3-en-2-yl]-6-chloro-9H-purin-2-amine
• CAS No.: 1315282-37-1
• Molecular Formula: C₂₈H₃₀ClN₅OSi
• Molecular Weight: 516.118

Synonyms:9-[(1R,2R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)bicyclo[3.1.0] hex-3-en-2-yl]-6-chloro-9H-purin-2-amine

Chemical Property of 9-[(1R,2R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)bicyclo[3.1.0] hex-3-en-2-yl]-6-chloro-9H-purin-2-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-[(1R,2R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)bicyclo[3.1.0] hex-3-en-2-yl]-6-chloro-9H-purin-2-amine

There total 9 articles about 9-[(1R,2R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)bicyclo[3.1.0] hex-3-en-2-yl]-6-chloro-9H-purin-2-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:

(1R,2S,5S)-5-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]bicyclo[3.1.0]hex-3-en-2-ol (870646-73-4) + 2-amino-6-chloropurine (10310-21-1) → 9-[(1R,2R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)bicyclo[3.1.0] hex-3-en-2-yl]-6-chloro-9H-purin-2-amine (1315282-37-1)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.bmc.2011.05.026

Reference yield:

(1S,5R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-oxa-bicyclo[3.1.0]hexan-2-one → 9-[(1R,2R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)bicyclo[3.1.0] hex-3-en-2-yl]-6-chloro-9H-purin-2-amine (1315282-37-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: diisobutylaluminium hydride / hexane; dichloromethane / 0.5 h / -78 °C / Inert atmosphere

2.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

4.2: Inert atmosphere

5.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

6.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; oxalyl dichloride; potassium tert-butylate; diisobutylaluminium hydride; dimethyl sulfoxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; 2.2: Wittig reaction / 3.1: Swern oxidation / 3.2: Swern oxidation / 4.1: Grignard reaction / 4.2: Grignard reaction / 6.1: Mitsunobu reaction;

DOI:10.1016/j.bmc.2011.05.026

Reference yield:

(1S,5R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-oxabicyclo[3.1.0]hexan-2-ol (917483-13-7) → 9-[(1R,2R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)bicyclo[3.1.0] hex-3-en-2-yl]-6-chloro-9H-purin-2-amine (1315282-37-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

3.1: tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

5.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; oxalyl dichloride; potassium tert-butylate; dimethyl sulfoxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 1.2: Wittig reaction / 2.1: Swern oxidation / 2.2: Swern oxidation / 3.1: Grignard reaction / 3.2: Grignard reaction / 5.1: Mitsunobu reaction;

DOI:10.1016/j.bmc.2011.05.026

upstream raw materials:

(1R,2S,5S)-5-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]bicyclo[3.1.0]hex-3-en-2-ol

2-amino-6-chloropurine

(1S,5R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-oxabicyclo[3.1.0]hexan-2-ol

(1R,2S)-[2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropyl]methanol

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