N⁶,O^5'-bis(4,4'-dimethoxytrityl)-9-<(2R)-2-azido-2,3-dideoxy-β-D-glycero-pentofuranosyl>adenine

Base Information

• Chemical Name: N⁶,O^5'-bis(4,4'-dimethoxytrityl)-9-<(2R)-2-azido-2,3-dideoxy-β-D-glycero-pentofuranosyl>adenine
• CAS No.: 114743-30-5
• Molecular Formula: C₅₂H₄₈N₈O₆
• Molecular Weight: 881.003

Synonyms:N⁶,O^5'-bis(4,4'-dimethoxytrityl)-9-<(2R)-2-azido-2,3-dideoxy-β-D-glycero-pentofuranosyl>adenine

Chemical Property of N⁶,O^5'-bis(4,4'-dimethoxytrityl)-9-<(2R)-2-azido-2,3-dideoxy-β-D-glycero-pentofuranosyl>adenine

Chemical Property:

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MSDS Files:

SDS file from LookChem

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Technology Process of N⁶,O^5'-bis(4,4'-dimethoxytrityl)-9-<(2R)-2-azido-2,3-dideoxy-β-D-glycero-pentofuranosyl>adenine

There total 12 articles about N⁶,O^5'-bis(4,4'-dimethoxytrityl)-9-<(2R)-2-azido-2,3-dideoxy-β-D-glycero-pentofuranosyl>adenine 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: 78.0%

N6,O5'-bis(4,4'-dimethoxytrityl)-9-(3-deoxy-2-O-mesyl-β-D-threo-pentofuranosyl)adenine (114743-29-2) → N6,O5'-bis(4,4'-dimethoxytrityl)-9-<(2R)-2-azido-2,3-dideoxy-β-D-glycero-pentofuranosyl>adenine (114743-30-5)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 110 ℃; for 4h;

DOI:10.1016/S0040-4039(01)83865-X

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → N6,O5'-bis(4,4'-dimethoxytrityl)-9-<(2R)-2-azido-2,3-dideoxy-β-D-glycero-pentofuranosyl>adenine (114743-30-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / pyridine / 3 h / Ambient temperature

2: 95 percent / Mg(OMe)2-NaBH₄ / benzene; methanol / 0.12 h / 65 °C

3: 93 percent / pyridine / 5 h / Ambient temperature

4: 78 percent / NaN₃ / dimethylformamide / 5 h / 105 - 110 °C

With pyridine; sodium tetrahydroborate; sodium azide; magnesium methanolate; In methanol; N,N-dimethyl-formamide; benzene;

DOI:10.1016/0008-6215(89)84088-1

Reference yield:

N6,O5'-bis(4,4'-dimethoxytrityl)-2'-O-tosyladenosine (109923-55-9) → N6,O5'-bis(4,4'-dimethoxytrityl)-9-<(2R)-2-azido-2,3-dideoxy-β-D-glycero-pentofuranosyl>adenine (114743-30-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / pyridine / 1 h / Ambient temperature

2: 87 percent / KOH-NaBH₄ / benzene; methanol / 24 h / Ambient temperature

3: 93 percent / pyridine / 5 h / Ambient temperature

4: 78 percent / NaN₃ / dimethylformamide / 5 h / 105 - 110 °C

With pyridine; potassium hydroxide; sodium tetrahydroborate; sodium azide; In methanol; N,N-dimethyl-formamide; benzene;

DOI:10.1016/0008-6215(89)84088-1

upstream raw materials:

N⁶,O^5'-bis(4,4'-dimethoxytrityl)-9-(3-deoxy-2-O-mesyl-β-D-threo-pentofuranosyl)adenine

2',3'-O-(dibutylstannylene)adenosine

4,4'-dimethoxytrityl chloride

N⁶,O⁵'-bis(4,4'-dimethoxytrityl)adenosine

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