1-<3'-C-(tert-butyldimethylsilyloxymethyl)-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-β-D-erythro-pentofuranosyl>-4-N-(p-nitrophenylethoxycarbonyl)cytosine

Base Information

• Chemical Name: 1-<3'-C-(tert-butyldimethylsilyloxymethyl)-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-β-D-erythro-pentofuranosyl>-4-N-(p-nitrophenylethoxycarbonyl)cytosine
• CAS No.: 188031-34-7
• Molecular Formula: C₃₁H₅₀N₄O₈Si₂
• Molecular Weight: 662.931

Synonyms:1-<3'-C-(tert-butyldimethylsilyloxymethyl)-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-β-D-erythro-pentofuranosyl>-4-N-(p-nitrophenylethoxycarbonyl)cytosine

Chemical Property of 1-<3'-C-(tert-butyldimethylsilyloxymethyl)-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-β-D-erythro-pentofuranosyl>-4-N-(p-nitrophenylethoxycarbonyl)cytosine

Chemical Property:

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Technology Process of 1-<3'-C-(tert-butyldimethylsilyloxymethyl)-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-β-D-erythro-pentofuranosyl>-4-N-(p-nitrophenylethoxycarbonyl)cytosine

There total 5 articles about 1-<3'-C-(tert-butyldimethylsilyloxymethyl)-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-β-D-erythro-pentofuranosyl>-4-N-(p-nitrophenylethoxycarbonyl)cytosine 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: 43.0%

2-(4-nitrophenyl)ethoxycarbonyl chloride (88091-68-3) + 1-<3'-C-(tert-butyldimethylsilyloxymethyl)-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-α,β-D-erythro-pentofuranosyl>cytosine (188031-43-8) → 1-<3'-C-(tert-butyldimethylsilyloxymethyl)-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-α-D-erythro-pentofuranosyl>-4-N-(p-nitrophenylethoxycarbonyl)cytosine (188031-45-0) + 1-<3'-C-(tert-butyldimethylsilyloxymethyl)-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-β-D-erythro-pentofuranosyl>-4-N-(p-nitrophenylethoxycarbonyl)cytosine (188031-34-7)

Guidance literature:

With pyridine; dmap; for 18h; Ambient temperature;

DOI:10.1039/a900800d

Reference yield:

(4R,5S)-4,5-bis(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-2-one (140156-23-6) → 1-<3'-C-(tert-butyldimethylsilyloxymethyl)-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-β-D-erythro-pentofuranosyl>-4-N-(p-nitrophenylethoxycarbonyl)cytosine (188031-34-7)

Guidance literature:

Multi-step reaction with 4 steps

1: DIBAL-H

With diisobutylaluminium hydride;

DOI:10.1039/a607699h

Reference yield:

(4R,5S)-4,5-Bis-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-ol → 1-<3'-C-(tert-butyldimethylsilyloxymethyl)-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-β-D-erythro-pentofuranosyl>-4-N-(p-nitrophenylethoxycarbonyl)cytosine (188031-34-7)

Guidance literature:

DOI:10.1039/a607699h

upstream raw materials:

2-(4-nitrophenyl)ethoxycarbonyl chloride

1-<3'-C-(tert-butyldimethylsilyloxymethyl)-5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-α,β-D-erythro-pentofuranosyl>cytosine

(4R,5S)-4,5-bis(tert-butyldimethylsilyloxymethyl)tetrahydrofuran-2-one

1-O-acetyl-3-C-(tert-butyldimethylsilyloxymethyl)-5-O-(tert-butyldimethylsilyl)-2,3-dideoxy-α,β-D-erythro-pentofuranose

Downstream raw materials:

1-<2',3'-dideoxy-3'-C-(hydroxymethyl)-β-D-erythro-pentofuranosyl>-4-N-(p-nitrophenylethoxycarbonyl)cytosine

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