2,6-anhydro-3,4,5-tri-O-benzyl-8,9-didehydro-7,8,9-trideoxy-D-glycero-L-gluco-nonuronic acid

Base Information

• Chemical Name: 2,6-anhydro-3,4,5-tri-O-benzyl-8,9-didehydro-7,8,9-trideoxy-D-glycero-L-gluco-nonuronic acid
• CAS No.: 497226-97-8
• Molecular Formula: C₃₀H₃₂O₆
• Molecular Weight: 488.58

Synonyms:2,6-anhydro-3,4,5-tri-O-benzyl-8,9-didehydro-7,8,9-trideoxy-D-glycero-L-gluco-nonuronic acid

Chemical Property of 2,6-anhydro-3,4,5-tri-O-benzyl-8,9-didehydro-7,8,9-trideoxy-D-glycero-L-gluco-nonuronic acid

Chemical Property:

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Technology Process of 2,6-anhydro-3,4,5-tri-O-benzyl-8,9-didehydro-7,8,9-trideoxy-D-glycero-L-gluco-nonuronic acid

There total 2 articles about 2,6-anhydro-3,4,5-tri-O-benzyl-8,9-didehydro-7,8,9-trideoxy-D-glycero-L-gluco-nonuronic acid 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: 67.0%

3-(2',3',4'-tri-O-benzyl-β-D-glucopyranosyl)-1-propene (497226-94-5) → 2,6-anhydro-3,4,5-tri-O-benzyl-8,9-didehydro-7,8,9-trideoxy-D-glycero-L-gluco-nonuronic acid (497226-97-8)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium hydrogencarbonate; potassium bromide; In acetone; at 0 - 20 ℃; for 21h;

DOI:10.1002/1099-0690(200210)2002:20<3411::AID-EJOC3411>3.0.CO;2-Q

Reference yield:

1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-2-propene (81972-19-2) → 2,6-anhydro-3,4,5-tri-O-benzyl-8,9-didehydro-7,8,9-trideoxy-D-glycero-L-gluco-nonuronic acid (497226-97-8)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / methanol / 20 h / 20 °C

2: 67 percent / Kbr, NaHCO₃; TEMPO; NaOCl / acetone / 21 h / 0 - 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium methylate; sodium hydrogencarbonate; potassium bromide; In methanol; acetone; 1: Zemplen;

DOI:10.1002/1099-0690(200210)2002:20<3411::AID-EJOC3411>3.0.CO;2-Q

Reference yield: 88.0%

2,6-anhydro-3,4,5-tri-O-benzyl-8,9-didehydro-7,8,9-trideoxy-D-glycero-L-gluco-nonuronic acid (497226-97-8) + methyl iodide (74-88-4) → methyl 2,6-anhydro-3,4,5-tri-O-benzyl-8,9-didehydro-7,8,9-trideoxy-D-glycero-L-gluco-nonuronate (497226-98-9)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1002/1099-0690(200210)2002:20<3411::AID-EJOC3411>3.0.CO;2-Q

upstream raw materials:

3-(2',3',4'-tri-O-benzyl-β-D-glucopyranosyl)-1-propene

1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-2-propene

Downstream raw materials:

(2S,3S,4R,5S,6S)-6-Allyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-carboxylic acid [(2R,3R,4R,5R)-3,4-bis-benzyloxy-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-2-ylmethyl]-amide

methyl 2,6-anhydro-3,4,5-tri-O-benzyl-8,9-didehydro-7,8,9-trideoxy-D-glycero-L-gluco-nonuronate

methyl 2,6-anhydro-3,4,5-tri-O-benzyl-7-deoxy-D-glycero-L-glucoocturonate

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