3'-azido-3'deoxy-5'-O{[(bis-benzyloxyphosphorylmethyl)benzyloxyphosphorylmethyl]benzyloxyphosphoryl}-N³-{1-[5-(2,2,2-trifluoroacetylamino)pentyl]}thymidine

Base Information

• Chemical Name: 3'-azido-3'deoxy-5'-O{[(bis-benzyloxyphosphorylmethyl)benzyloxyphosphorylmethyl]benzyloxyphosphoryl}-N³-{1-[5-(2,2,2-trifluoroacetylamino)pentyl]}thymidine
• CAS No.: 174571-56-3
• Molecular Formula: C₄₇H₅₄F₃N₆O₁₂P₃
• Molecular Weight: 1044.9

Synonyms:3'-azido-3'deoxy-5'-O{[(bis-benzyloxyphosphorylmethyl)benzyloxyphosphorylmethyl]benzyloxyphosphoryl}-N³-{1-[5-(2,2,2-trifluoroacetylamino)pentyl]}thymidine

Chemical Property of 3'-azido-3'deoxy-5'-O{[(bis-benzyloxyphosphorylmethyl)benzyloxyphosphorylmethyl]benzyloxyphosphoryl}-N³-{1-[5-(2,2,2-trifluoroacetylamino)pentyl]}thymidine

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Technology Process of 3'-azido-3'deoxy-5'-O{[(bis-benzyloxyphosphorylmethyl)benzyloxyphosphorylmethyl]benzyloxyphosphoryl}-N³-{1-[5-(2,2,2-trifluoroacetylamino)pentyl]}thymidine

There total 7 articles about 3'-azido-3'deoxy-5'-O{[(bis-benzyloxyphosphorylmethyl)benzyloxyphosphorylmethyl]benzyloxyphosphoryl}-N³-{1-[5-(2,2,2-trifluoroacetylamino)pentyl]}thymidine 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: 47.0%

<<(Benzyloxy)<<(benzyloxy)hydroxyphosphoryl>methyl>phosphoryl>methyl>phosphonic acid dibenzyl ester (165271-67-0) + 3'-azido-3'-deoxy-N3-{1-[5-(2,2,2-trifluoroacetylamino)pentyl]}thymidine (174571-55-2) → 3'-azido-3'deoxy-5'-O{[(bis-benzyloxyphosphorylmethyl)benzyloxyphosphorylmethyl]benzyloxyphosphoryl}-N3-{1-[5-(2,2,2-trifluoroacetylamino)pentyl]}thymidine (174571-56-3) + [((2S,3S,5R)-3-Azido-5-{5-methyl-2,4-dioxo-3-[5-(2,2,2-trifluoro-acetylamino)-pentyl]-3,4-dihydro-2H-pyrimidin-1-yl}-tetrahydro-furan-2-ylmethoxy)-(bis-benzyloxy-phosphorylmethyl)-phosphinoylmethyl]-phosphonic acid dibenzyl ester

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1021/jo982502p

Reference yield: 47.0%

<<(Benzyloxy)<<(benzyloxy)hydroxyphosphoryl>methyl>phosphoryl>methyl>phosphonic acid dibenzyl ester (165271-67-0) + 3'-azido-3'-deoxy-N3-{1-[5-(2,2,2-trifluoroacetylamino)pentyl]}thymidine (174571-55-2) → 3'-azido-3'deoxy-5'-O{[(bis-benzyloxyphosphorylmethyl)benzyloxyphosphorylmethyl]benzyloxyphosphoryl}-N3-{1-[5-(2,2,2-trifluoroacetylamino)pentyl]}thymidine (174571-56-3)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine;

DOI:10.1016/S0040-4039(99)00497-9

Reference yield:

2,2,2-trifluoro-N-(5-hydroxypentyl)acetamide (128238-44-8) → 3'-azido-3'deoxy-5'-O{[(bis-benzyloxyphosphorylmethyl)benzyloxyphosphorylmethyl]benzyloxyphosphoryl}-N3-{1-[5-(2,2,2-trifluoroacetylamino)pentyl]}thymidine (174571-56-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / Ph₃P; diisopropyl azodicarboxylate / tetrahydrofuran / 0.5 h / 20 °C

2: 72 percent / potassium carbonate / methanol / 1.5 h / 20 °C

3: 47 percent / Ph₃P; diisopropyl azodicarboxylate / tetrahydrofuran / 4 h / 20 °C

With di-isopropyl azodicarboxylate; potassium carbonate; triphenylphosphine; In tetrahydrofuran; methanol; 1: Substitution / 2: Hydrolysis / 3: Substitution;

DOI:10.1021/jo982502p

upstream raw materials:

<<(Benzyloxy)<<(benzyloxy)hydroxyphosphoryl>methyl>phosphoryl>methyl>phosphonic acid dibenzyl ester

3'-azido-3'-deoxy-N³-{1-[5-(2,2,2-trifluoroacetylamino)pentyl]}thymidine

3'-Azido-5'-O-(4-methoxybenzoyl)-3'-deoxythymidine

2,2,2-trifluoro-N-(5-hydroxypentyl)acetamide

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