9-[(1R,2R,5S)-5-(tert-butyl-diphenylsilanyloxymethyl)bicyclo[3.1.0]hex-3-en-2-yl]-6-chloro-9H-purine

Base Information

Chemical Name:9-[(1R,2R,5S)-5-(tert-butyl-diphenylsilanyloxymethyl)bicyclo[3.1.0]hex-3-en-2-yl]-6-chloro-9H-purine
CAS No.:1315282-36-0
Molecular Formula:C₂₈H₂₉ClN₄OSi
Molecular Weight:501.103
Hs Code.:

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

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

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

There total 9 articles about 9-[(1R,2R,5S)-5-(tert-butyl-diphenylsilanyloxymethyl)bicyclo[3.1.0]hex-3-en-2-yl]-6-chloro-9H-purine 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: 21.0%

: 870646-73-4
(1R,2S,5S)-5-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]bicyclo[3.1.0]hex-3-en-2-ol

: 87-42-3,111055-92-6
6-chloro-7H-purine

: 1315282-36-0
9-[(1R,2R,5S)-5-(tert-butyl-diphenylsilanyloxymethyl)bicyclo[3.1.0]hex-3-en-2-yl]-6-chloro-9H-purine

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 ℃; for 1h; Inert atmosphere;
DOI:10.1016/j.bmc.2011.05.026

Reference yield:

: 917483-13-7
(1S,5R)-1-(tert-butyl-diphenyl-silanyloxymethyl)-3-oxabicyclo[3.1.0]hexan-2-ol

: 1315282-36-0
9-[(1R,2R,5S)-5-(tert-butyl-diphenylsilanyloxymethyl)bicyclo[3.1.0]hex-3-en-2-yl]-6-chloro-9H-purine

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

Reference yield:

: 917483-15-9
(1R,2S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-2-vinylcyclopropanecarbaldehyde

: 1315282-36-0
9-[(1R,2R,5S)-5-(tert-butyl-diphenylsilanyloxymethyl)bicyclo[3.1.0]hex-3-en-2-yl]-6-chloro-9H-purine

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: Inert atmosphere

2.1: 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

3.1: 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; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 1.1: Grignard reaction / 1.2: Grignard reaction / 3.1: Mitsunobu reaction;
DOI:10.1016/j.bmc.2011.05.026