(N)-methanocarba-N⁶-methyl-2-chloro-2'-deoxyadenosine-3',5'-bis(dibenzyl phosphate)

Base Information

• Chemical Name: (N)-methanocarba-N⁶-methyl-2-chloro-2'-deoxyadenosine-3',5'-bis(dibenzyl phosphate)
• CAS No.: 264611-16-7
• Molecular Formula: C₄₁H₄₂ClN₅O₈P₂
• Molecular Weight: 830.214

Synonyms:(N)-methanocarba-N⁶-methyl-2-chloro-2'-deoxyadenosine-3',5'-bis(dibenzyl phosphate)

Chemical Property of (N)-methanocarba-N⁶-methyl-2-chloro-2'-deoxyadenosine-3',5'-bis(dibenzyl phosphate)

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (N)-methanocarba-N⁶-methyl-2-chloro-2'-deoxyadenosine-3',5'-bis(dibenzyl phosphate)

There total 5 articles about (N)-methanocarba-N⁶-methyl-2-chloro-2'-deoxyadenosine-3',5'-bis(dibenzyl phosphate) 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: 35.0%

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate (990-91-0) + (1R,2S,4S,5S)-1-[(hydroxy)methyl]-2-hydroxy-4-(2-chloro-6-methylaminopurin-9-yl)bicyclo[3.1.0]hexane (264610-99-3) → (N)-methanocarba-N6-methyl-2-chloro-2'-deoxyadenosine-3',5'-bis(dibenzyl phosphate) (264611-16-7)

Guidance literature:

(1R,2S,4S,5S)-1-[(hydroxy)methyl]-2-hydroxy-4-(2-chloro-6-methylaminopurin-9-yl)bicyclo[3.1.0]hexane; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.25h;

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate; In tetrahydrofuran; at -78 - 20 ℃; Further stages.;

DOI:10.1021/jm990249v

Reference yield:

2,6 dichloropurine (5451-40-1) → (N)-methanocarba-N6-methyl-2-chloro-2'-deoxyadenosine-3',5'-bis(dibenzyl phosphate) (264611-16-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 64 percent / Ph₃P; DEAD / tetrahydrofuran / 12 h / 20 °C

2.1: 88 percent / methanol / 12 h / 20 °C

3.1: 39.6 percent / BCl₃ / CH₂Cl₂ / 0.83 h / -78 °C

4.1: LDA / tetrahydrofuran / 0.25 h / -78 °C

4.2: 35 percent / tetrahydrofuran / -78 - 20 °C

With boron trichloride; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; 1.1: Substitution / 2.1: Substitution / 3.1: Debenzylation / 4.1: Metallation / 4.2: Phosphorylation;

DOI:10.1021/jm990249v

Reference yield:

(1S,2R,4S,5R)-4-(phenylmethoxy)-5-[(phenylmethoxy)methyl]bicyclo[3.1.0]hexan-2-ol (259659-49-9) → (N)-methanocarba-N6-methyl-2-chloro-2'-deoxyadenosine-3',5'-bis(dibenzyl phosphate) (264611-16-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 64 percent / Ph₃P; DEAD / tetrahydrofuran / 12 h / 20 °C

2.1: 88 percent / methanol / 12 h / 20 °C

3.1: 39.6 percent / BCl₃ / CH₂Cl₂ / 0.83 h / -78 °C

4.1: LDA / tetrahydrofuran / 0.25 h / -78 °C

4.2: 35 percent / tetrahydrofuran / -78 - 20 °C

With boron trichloride; triphenylphosphine; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; 1.1: Substitution / 2.1: Substitution / 3.1: Debenzylation / 4.1: Metallation / 4.2: Phosphorylation;

DOI:10.1021/jm990249v

upstream raw materials:

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

(1R,2S,4S,5S)-1-[(hydroxy)methyl]-2-hydroxy-4-(2-chloro-6-methylaminopurin-9-yl)bicyclo[3.1.0]hexane

2,6 dichloropurine

(1S,2R,4S,5R)-4-(phenylmethoxy)-5-[(phenylmethoxy)methyl]bicyclo[3.1.0]hexan-2-ol

Downstream raw materials:

MRS 2279

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