4S-{(1R,6S,9R)-7-N-benzyl-3,7-diaza-8-oxa-2-oxobicylo[4,3,0]nonan-9-yl}-2,3-di-O-tert-butyldimethylsilyl-1-(uracil-1-yl)-β-D-erythro-furanose

Base Information

• Chemical Name: 4S-{(1R,6S,9R)-7-N-benzyl-3,7-diaza-8-oxa-2-oxobicylo[4,3,0]nonan-9-yl}-2,3-di-O-tert-butyldimethylsilyl-1-(uracil-1-yl)-β-D-erythro-furanose
• CAS No.: 1603836-05-0
• Molecular Formula: C₃₃H₅₂N₄O₇Si₂
• Molecular Weight: 672.969

Synonyms:4S-{(1R,6S,9R)-7-N-benzyl-3,7-diaza-8-oxa-2-oxobicylo[4,3,0]nonan-9-yl}-2,3-di-O-tert-butyldimethylsilyl-1-(uracil-1-yl)-β-D-erythro-furanose

Chemical Property of 4S-{(1R,6S,9R)-7-N-benzyl-3,7-diaza-8-oxa-2-oxobicylo[4,3,0]nonan-9-yl}-2,3-di-O-tert-butyldimethylsilyl-1-(uracil-1-yl)-β-D-erythro-furanose

Chemical Property:

Purity/Quality:

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Technology Process of 4S-{(1R,6S,9R)-7-N-benzyl-3,7-diaza-8-oxa-2-oxobicylo[4,3,0]nonan-9-yl}-2,3-di-O-tert-butyldimethylsilyl-1-(uracil-1-yl)-β-D-erythro-furanose

There total 11 articles about 4S-{(1R,6S,9R)-7-N-benzyl-3,7-diaza-8-oxa-2-oxobicylo[4,3,0]nonan-9-yl}-2,3-di-O-tert-butyldimethylsilyl-1-(uracil-1-yl)-β-D-erythro-furanose 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: 60.0%

4S-{(1R,6S,9R)-5-(7-N-benzyl-3-N-(2-cyanoethyl)-3,7-diaza-8-oxa-2-oxobicylo[4,3,0]nonan-9-yl)}-2,3-di-O-tert-butyldimethylsilyl-1-(uracil-1-yl)-β-D-erythro-furanose (1603836-09-4) → 4S-{(1R,6S,9R)-7-N-benzyl-3,7-diaza-8-oxa-2-oxobicylo[4,3,0]nonan-9-yl}-2,3-di-O-tert-butyldimethylsilyl-1-(uracil-1-yl)-β-D-erythro-furanose (1603836-05-0)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1002/ejoc.201400140 DOI:10.1002/ejoc.201400140

Reference yield:

2',3'-bis-O-(tert-butyldimethylsilyl)uridine (87418-87-9,69504-12-7) → 4S-{(1R,6S,9R)-7-N-benzyl-3,7-diaza-8-oxa-2-oxobicylo[4,3,0]nonan-9-yl}-2,3-di-O-tert-butyldimethylsilyl-1-(uracil-1-yl)-β-D-erythro-furanose (1603836-05-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 8 h / Reflux

2.1: zinc trifluoromethanesulfonate; N,N,N,N,-tetramethylethylenediamine; triethylamine / tetrahydrofuran / 0.17 h / 20 °C

2.2: 48 h / 20 °C

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; acetonitrile / 3 h / 20 °C

4.1: acetonitrile / 96 h / Molecular sieve; Reflux

5.1: potassium tert-butylate / tetrahydrofuran / 1 h / 0 °C

With N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate; zinc trifluoromethanesulfonate; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dimethyl sulfoxide; acetonitrile; 2.1: |Horner-Wadsworth-Emmons Olefination / 2.2: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1002/ejoc.201400140

Reference yield:

(E)-N-(2-cyanoethyl)-N-(3-hydroxylpropyl)-2,3-di-O-tert-butyldimethylsilyl-5,6-dideoxy-1-(uracil-1yl)-β-D-ribo-5-ene-1-(uracil-1yl)heptofuranuronamide (1603835-99-9) → 4S-{(1R,6S,9R)-7-N-benzyl-3,7-diaza-8-oxa-2-oxobicylo[4,3,0]nonan-9-yl}-2,3-di-O-tert-butyldimethylsilyl-1-(uracil-1-yl)-β-D-erythro-furanose (1603836-05-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; acetonitrile / 3 h / 20 °C

2: acetonitrile / 96 h / Molecular sieve; Reflux

3: potassium tert-butylate / tetrahydrofuran / 1 h / 0 °C

With potassium tert-butylate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dimethyl sulfoxide; acetonitrile;

DOI:10.1002/ejoc.201400140

upstream raw materials:

(2S,3R,4R,5R)-3,4-bis(tert-butyldimethylsilanyloxy)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydrofuran-2-carbaldehyde

2',3'-bis-O-(tert-butyldimethylsilyl)uridine

N-benzyl hydroxylalmine

N-3-hydroxylpropyl diethylphosphonoacetamide

Downstream raw materials:

4S-{(1S,6R,9S)-7-N-benzyl-3,7-diaza-8-oxa-2-oxobicylo[4,3,0]nonan-9-yl}-2,3-di-O-tert-butyldimethylsilyl-1-(uracil-1-yl)-β-D-erythro-furanose

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