ethyl 3-cyano-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-2-carboxylate

Base Information

• Chemical Name: ethyl 3-cyano-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-2-carboxylate
• CAS No.: 136947-14-3
• Molecular Formula: C₃₄H₃₄N₂O₆
• Molecular Weight: 566.654

Synonyms:ethyl 3-cyano-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-2-carboxylate

Chemical Property of ethyl 3-cyano-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-2-carboxylate

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Technology Process of ethyl 3-cyano-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-2-carboxylate

There total 1 articles about ethyl 3-cyano-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-2-carboxylate 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:

2,3,5-tri-Obenzyl-α,β-D-ribofuranosylchloride (50619-36-8) + 3-Cyan-2-pyrrolcarbonsaeure-ethylester (7126-44-5) → ethyl 3-cyano-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-2-carboxylate (136947-14-3)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction; 1.) MeCN, RT, 40 min, 2.) MeCN, RT, 27 h;

DOI:10.1021/jm00081a014

Reference yield: 72.6%

ethyl 3-cyano-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-2-carboxylate (136947-14-3) → 4-Amino-1-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1,6-dihydro-pyrrolo[2,3-d]pyridazin-7-one (185454-56-2)

Guidance literature:

With hydrazine; In ethanol; for 48h; Heating;

DOI:10.1021/jm960631x

Reference yield: 28.78%

ethyl 3-cyano-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-2-carboxylate (136947-14-3) → 3-cyano-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-2-carboxylic acid (136947-15-4)

Guidance literature:

With potassium hydroxide; In ethanol; water; for 1.5h; Heating;

DOI:10.1021/jm00081a014

upstream raw materials:

2,3,5-tri-Obenzyl-α,β-D-ribofuranosylchloride

3-Cyan-2-pyrrolcarbonsaeure-ethylester

Downstream raw materials:

3-cyano-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole-2-carboxylic acid

4-Amino-1-((2R,3S,4R,5R)-3,4-bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-1,6-dihydro-pyrrolo[2,3-d]pyridazin-7-one

3-cyano-2-formyl-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)pyrrole

1-((2R,3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-3-cyano-1H-pyrrole-2-carbonyl chloride

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