1-[(3S,4R)-6-(diethoxyphosphinyl)-2,5,6-trideoxy-β-hexofuranosyl]thymine

Base Information

• Chemical Name: 1-[(3S,4R)-6-(diethoxyphosphinyl)-2,5,6-trideoxy-β-hexofuranosyl]thymine
• CAS No.: 124685-23-0
• Molecular Formula: C₁₅H₂₅N₂O₇P
• Molecular Weight: 376.346

Synonyms:1-[(3S,4R)-6-(diethoxyphosphinyl)-2,5,6-trideoxy-β-hexofuranosyl]thymine

Chemical Property of 1-[(3S,4R)-6-(diethoxyphosphinyl)-2,5,6-trideoxy-β-hexofuranosyl]thymine

Chemical Property:

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Technology Process of 1-[(3S,4R)-6-(diethoxyphosphinyl)-2,5,6-trideoxy-β-hexofuranosyl]thymine

There total 1 articles about 1-[(3S,4R)-6-(diethoxyphosphinyl)-2,5,6-trideoxy-β-hexofuranosyl]thymine 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:

Diethyl vinylphosphonate (682-30-4) + 2′-deoxy-5′-O-phthalimidonucleoside (140659-85-4) → 1-[(3S,4S)-6-(diethoxyphosphinyl)-2,5,6-trideoxy-α-hexofuranosyl]thymine + 1-[(3S,4R)-6-(diethoxyphosphinyl)-2,5,6-trideoxy-β-hexofuranosyl]thymine (124685-23-0) + thymidine (50-89-5,28854-96-8,3545-96-8,50-88-4)

Guidance literature:

With tris[2-phenylpyridinato-C₂,N]iridium(III); diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; In 1,4-dioxane; at 20 ℃; for 1h; Temperature; Solvent; Inert atmosphere; Irradiation;

DOI:10.1021/acs.joc.8b00637

Reference yield: 60.0%

1-[(3'R,4'R)-2',5',6'-trideoxy-6'-(diethoxyphosphinyl)-β-hexofuranosyl]thymine (124685-23-0) + benzoic acid (65-85-0,8013-63-6) → 1-[(3'S,4'R)-3'-O-benzoyl-2',5',6'-trideoxy-6'-(diethoxyphosphinyl)-β-hexofuranosyl]thymine (500018-96-2)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 20h;

DOI:10.1002/1522-2675(200209)85:9<2777::AID-HLCA2777>3.0.CO;2-1

Reference yield:

1-[(3'R,4'R)-2',5',6'-trideoxy-6'-(diethoxyphosphinyl)-β-hexofuranosyl]thymine (124685-23-0) → 1-[(3'S,4'R)-3'-O-benzoyl-2',5',6'-trideoxy-6'-(ethoxyhydroxyphosphinyl)-β-hexofuranosyl]thymine (500018-97-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / PPh₃; DIAD / tetrahydrofuran / 20 h / 0 - 20 °C

2: 75 percent / LiBr / pyridine / 4 h / Heating

With di-isopropyl azodicarboxylate; triphenylphosphine; lithium bromide; In tetrahydrofuran; pyridine; 1: Mitsunobu reaction;

DOI:10.1002/1522-2675(200209)85:9<2777::AID-HLCA2777>3.0.CO;2-1

upstream raw materials:

Diethyl vinylphosphonate

2′-deoxy-5′-O-phthalimidonucleoside

Downstream raw materials:

1-[(3'S,4'R)-3'-O-benzoyl-2',5',6'-trideoxy-6'-(diethoxyphosphinyl)-β-hexofuranosyl]thymine

1-[(3'S,4'R)-3'-O-benzoyl-2',5',6'-trideoxy-6'-(ethoxyhydroxyphosphinyl)-β-hexofuranosyl]thymine

2'-Deoxy-O^P-ethyl-5'-O-(4,4'-dimethoxytrityl)thymidylylmethylene-(3'->5')-2',5'-dideoxythymidine

2'-deoxy-O^P-ethyl-5'-O-(4,4'-dimethoxytrityl)thymidylylmethylene-(3'->5')-3'-O-benzoyl-2',5'-dideoxythymidine

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