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

Base Information

• Chemical Name: (1R,2S,4S,5S)-1-[(benzyloxy)methyl]-2-benzyloxy-4-(2-chloro-6-methylaminopurin-9-yl)bicyclo[3.1.0]hexane
• CAS No.: 264610-98-2
• Molecular Formula: C₂₇H₂₈ClN₅O₂
• Molecular Weight: 490.005

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

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

Chemical Property:

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

There total 3 articles about (1R,2S,4S,5S)-1-[(benzyloxy)methyl]-2-benzyloxy-4-(2-chloro-6-methylaminopurin-9-yl)bicyclo[3.1.0]hexane 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: 88.0%

methylamine (74-89-5) + (1R,2S,4S,5S)-1-[(benzyloxy)methyl]-2-benzyloxy-4-(2,6-dichloropurin-9-yl)bicyclo[3.1.0]hexane (264610-97-1) → (1R,2S,4S,5S)-1-[(benzyloxy)methyl]-2-benzyloxy-4-(2-chloro-6-methylaminopurin-9-yl)bicyclo[3.1.0]hexane (264610-98-2)

Guidance literature:

In methanol; at 20 ℃; for 12h;

DOI:10.1021/jm990249v

Reference yield:

2,6 dichloropurine (5451-40-1) → (1R,2S,4S,5S)-1-[(benzyloxy)methyl]-2-benzyloxy-4-(2-chloro-6-methylaminopurin-9-yl)bicyclo[3.1.0]hexane (264610-98-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / Ph₃P; DEAD / tetrahydrofuran / 12 h / 20 °C

2: 88 percent / methanol / 12 h / 20 °C

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; 1: Substitution / 2: Substitution;

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) → (1R,2S,4S,5S)-1-[(benzyloxy)methyl]-2-benzyloxy-4-(2-chloro-6-methylaminopurin-9-yl)bicyclo[3.1.0]hexane (264610-98-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / Ph₃P; DEAD / tetrahydrofuran / 12 h / 20 °C

2: 88 percent / methanol / 12 h / 20 °C

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; 1: Substitution / 2: Substitution;

DOI:10.1021/jm990249v

upstream raw materials:

methylamine

(1R,2S,4S,5S)-1-[(benzyloxy)methyl]-2-benzyloxy-4-(2,6-dichloropurin-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:

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

MRS 2279

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