1-<5,6-dideoxy-2,3-O-isopropylidene-6-(p-toluenesulfonyl)-β-D-ribo-hex-5(E)-enofuranosyl>uracil

Base Information

• Chemical Name: 1-<5,6-dideoxy-2,3-O-isopropylidene-6-(p-toluenesulfonyl)-β-D-ribo-hex-5(E)-enofuranosyl>uracil
• CAS No.: 138310-61-9
• Molecular Formula: C₂₀H₂₂N₂O₇S
• Molecular Weight: 434.47

Synonyms:1-<5,6-dideoxy-2,3-O-isopropylidene-6-(p-toluenesulfonyl)-β-D-ribo-hex-5(E)-enofuranosyl>uracil

Chemical Property of 1-<5,6-dideoxy-2,3-O-isopropylidene-6-(p-toluenesulfonyl)-β-D-ribo-hex-5(E)-enofuranosyl>uracil

Chemical Property:

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Technology Process of 1-<5,6-dideoxy-2,3-O-isopropylidene-6-(p-toluenesulfonyl)-β-D-ribo-hex-5(E)-enofuranosyl>uracil

There total 2 articles about 1-<5,6-dideoxy-2,3-O-isopropylidene-6-(p-toluenesulfonyl)-β-D-ribo-hex-5(E)-enofuranosyl>uracil 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:

{[(4-methylphenyl)sulfonyl]methylidene}(triphenyl)-λ5-phosphane (5554-81-4) + (3aS,4S,6R,6aR)-6-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde (27999-65-1) → 1-<5,6-dideoxy-2,3-O-isopropylidene-6-(p-toluenesulfonyl)-β-D-ribo-hex-5(E)-enofuranosyl>uracil (138310-61-9)

Guidance literature:

In dimethyl sulfoxide; at 35 ℃; for 5h; Yield given;

DOI:10.1139/v91-303

Reference yield:

2',3'-O-isopropylideneuridine (362-43-6) → 1-<5,6-dideoxy-2,3-O-isopropylidene-6-(p-toluenesulfonyl)-β-D-ribo-hex-5(E)-enofuranosyl>uracil (138310-61-9)

Guidance literature:

Multi-step reaction with 2 steps

1: dicyclohexylcarbodiimide, pyridinium trifluoroacetate, DMSO / Ambient temperature

2: dimethylsulfoxide / 5 h / 35 °C

With pyridinium trifluroacetate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; In dimethyl sulfoxide;

DOI:10.1139/v91-303

Reference yield: 91.0%

1-<5,6-dideoxy-2,3-O-isopropylidene-6-(p-toluenesulfonyl)-β-D-ribo-hex-5(E)-enofuranosyl>uracil (138310-61-9) → 1-<5,6-dideoxy-2,3-O-isopropylidene-6-(p-toluenesulfonyl)-β-D-erythro-hex-4-(Z)-enofuranosyl>uracil (138310-62-0)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; acetonitrile; for 4h; Ambient temperature;

DOI:10.1139/v91-303

upstream raw materials:

{[(4-methylphenyl)sulfonyl]methylidene}(triphenyl)-λ⁵-phosphane

(3aS,4S,6R,6aR)-6-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carbaldehyde

2',3'-O-isopropylideneuridine

Downstream raw materials:

1-<5,6-dideoxy-2,3-O-isopropylidene-6,5-methylthio-(p-toluenesulfonyl)-β-D-ribo-hexofuranosyl>uracil

1-<5(R)-acetamido-5,6-dideoxy-2,3-O-isopropylidene-6-(p-toluenesulfonyl)-β-D-ribo-hexofuranosyl>uracil

1-<5(S)-acetamido-5,6-dideoxy-2,3-O-isopropylidene-6-(p-toluenesulfonyl)-β-D-ribo-hexofuranosyl>uracil

1-<5,6-dideoxy-6-(p-toluenesulfonyl)-β-D-ribo-hex-5(E)-enofuranosyl>uracil

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