methyl <4,5,7-tri-O-benzyl-2,3-dideoxy-β-D-arabino-2-heptulopyranosid>onate

Base Information

• Chemical Name: methyl <4,5,7-tri-O-benzyl-2,3-dideoxy-β-D-arabino-2-heptulopyranosid>onate
• CAS No.: 119005-71-9
• Molecular Formula: C₂₉H₃₂O₆
• Molecular Weight: 476.569

Synonyms:methyl <4,5,7-tri-O-benzyl-2,3-dideoxy-β-D-arabino-2-heptulopyranosid>onate

Chemical Property of methyl <4,5,7-tri-O-benzyl-2,3-dideoxy-β-D-arabino-2-heptulopyranosid>onate

Chemical Property:

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Technology Process of methyl <4,5,7-tri-O-benzyl-2,3-dideoxy-β-D-arabino-2-heptulopyranosid>onate

There total 12 articles about methyl <4,5,7-tri-O-benzyl-2,3-dideoxy-β-D-arabino-2-heptulopyranosid>onate 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: 95.0%

methyl (4R,5S,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-5,6-dihydro-4H-pyran-2-carboxylate (110390-66-4) → methyl <4,5,7-tri-O-benzyl-2,3-dideoxy-β-D-arabino-2-heptulopyranosid>onate (119005-71-9)

Guidance literature:

With hydrogen; triethylamine; palladium on activated charcoal; In methanol; ethyl acetate; for 1h; under 760 Torr;

DOI:10.1021/jo060913x

Reference yield: 53.0%

methyl chloroformate (79-22-1) + tributyl-(3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexapyranosyl)stannane (98933-74-5,98933-75-6) → methyl <4,5,7-tri-O-benzyl-2,3-dideoxy-β-D-arabino-2-heptulopyranosid>onate (119005-71-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; 1.) -78 deg C, 10 min, 2.) -78 deg C, 1 h;

DOI:10.1039/P19960000431

Reference yield: 50.0%

methanol (67-56-1) + (4R,5S,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-carbonitrile → methyl <4,5,7-tri-O-benzyl-2,3-dideoxy-β-D-arabino-2-heptulopyranosid>onate (119005-71-9) + methyl <4,5,7-tri-O-benzyl-2,3-dideoxy-α-D-arabino-2-heptulopyranosid>onate (119005-72-0)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 14h;

DOI:10.1039/c6ob02154a

upstream raw materials:

methyl onate

methyl onate

methyl chloroformate

tributyl-(3,4,6-tri-O-benzyl-2-deoxy-β-D-arabino-hexapyranosyl)stannane

Downstream raw materials:

(2R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-tert-butoxycarbonylmethyl-tetrahydro-pyran-2-carboxylic acid methyl ester

(2R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-tert-butoxycarbonylmethyl-tetrahydro-pyran-2-carboxylic acid

3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl formaldehyde

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