1-[2,3-dideoxy-6-O-(4,4'-dimethoxytrityl)-3-phthalimido-α-D-arabino-hexofuranosyl]thymine

Base Information

• Chemical Name: 1-[2,3-dideoxy-6-O-(4,4'-dimethoxytrityl)-3-phthalimido-α-D-arabino-hexofuranosyl]thymine
• CAS No.: 676132-93-7
• Molecular Formula: C₄₀H₃₇N₃O₉
• Molecular Weight: 703.748

Synonyms:1-[2,3-dideoxy-6-O-(4,4'-dimethoxytrityl)-3-phthalimido-α-D-arabino-hexofuranosyl]thymine

Chemical Property of 1-[2,3-dideoxy-6-O-(4,4'-dimethoxytrityl)-3-phthalimido-α-D-arabino-hexofuranosyl]thymine

Chemical Property:

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Technology Process of 1-[2,3-dideoxy-6-O-(4,4'-dimethoxytrityl)-3-phthalimido-α-D-arabino-hexofuranosyl]thymine

There total 2 articles about 1-[2,3-dideoxy-6-O-(4,4'-dimethoxytrityl)-3-phthalimido-α-D-arabino-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: 64.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + 2-[(2S,3R,5S)-2-((R)-1,2-Dihydroxy-ethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-isoindole-1,3-dione (676132-92-6) → 1-[2,3-dideoxy-6-O-(4,4'-dimethoxytrityl)-3-phthalimido-α-D-arabino-hexofuranosyl]thymine (676132-93-7)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1016/j.bmcl.2003.11.075

Reference yield:

1-(5,6-Di-O-acetyl-2,3-dideoxy-3-phthalimido-α-D-arabino-hexafuranosyl)thymine (133488-19-4) → 1-[2,3-dideoxy-6-O-(4,4'-dimethoxytrityl)-3-phthalimido-α-D-arabino-hexofuranosyl]thymine (676132-93-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / Et₃N; MeOH / 4 h / Heating

2: 64 percent / pyridine / 20 °C

With pyridine; methanol; triethylamine;

DOI:10.1016/j.bmcl.2003.11.075

Reference yield: 75.0%

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) + 1-[2,3-dideoxy-6-O-(4,4'-dimethoxytrityl)-3-phthalimido-α-D-arabino-hexofuranosyl]thymine (676132-93-7) → 1-{2,3-dideoxy-6-O-[4,4'-dimethoxytrityl]-5-O-[2-cyanoethoxy(diisopropylamino)phosphino]-3-phthalimido-α-D-arabino-hexofuranosyl}thymine

Guidance literature:

With N,N-diisopropylamine tetrazolide; In dichloromethane;

DOI:10.1016/j.bmcl.2003.11.075

upstream raw materials:

4,4'-dimethoxytrityl chloride

2-[(2S,3R,5S)-2-((R)-1,2-Dihydroxy-ethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl]-isoindole-1,3-dione

1-(5,6-Di-O-acetyl-2,3-dideoxy-3-phthalimido-α-D-arabino-hexafuranosyl)thymine

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