Benzoic acid (2R,3S,4S,5R,6R)-3-[(2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-2-yloxy]-5-hydroxy-6-hydroxymethyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Benzoic acid (2R,3S,4S,5R,6R)-3-[(2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-2-yloxy]-5-hydroxy-6-hydroxymethyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-4-yl ester
• CAS No.: 84594-50-3
• Molecular Formula: C₃₉H₃₈N₂O₁₈
• Molecular Weight: 822.733

Synonyms:

Chemical Property of Benzoic acid (2R,3S,4S,5R,6R)-3-[(2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-2-yloxy]-5-hydroxy-6-hydroxymethyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-4-yl ester

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Technology Process of Benzoic acid (2R,3S,4S,5R,6R)-3-[(2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-2-yloxy]-5-hydroxy-6-hydroxymethyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-4-yl ester

There total 3 articles about Benzoic acid (2R,3S,4S,5R,6R)-3-[(2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-2-yloxy]-5-hydroxy-6-hydroxymethyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-4-yl ester 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:

p-nitrophenyl 3-O-benzoyl-4,6-O-benzylidene-2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-mannopyranoside (84564-28-3) → Benzoic acid (2R,3S,4S,5R,6R)-3-[(2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-2-yloxy]-5-hydroxy-6-hydroxymethyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-4-yl ester (84594-50-3)

Guidance literature:

With acetic acid; at 100 ℃; for 0.25h;

DOI:10.1016/0008-6215(82)85025-8

Reference yield:

p-nitrophenyl 3-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside (94062-91-6) → Benzoic acid (2R,3S,4S,5R,6R)-3-[(2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-2-yloxy]-5-hydroxy-6-hydroxymethyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-4-yl ester (84594-50-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 31 percent / Hg(CN)2 / acetonitrile / 48 h / 4 °C

2: 0.19 g / 80percent AcOH / 0.25 h / 100 °C

With mercury(II) cyanide; acetic acid; In acetonitrile;

DOI:10.1016/0008-6215(82)85025-8

Reference yield:

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (10028-45-2) → Benzoic acid (2R,3S,4S,5R,6R)-3-[(2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-2-yloxy]-5-hydroxy-6-hydroxymethyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-4-yl ester (84594-50-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 31 percent / Hg(CN)2 / acetonitrile / 48 h / 4 °C

2: 0.19 g / 80percent AcOH / 0.25 h / 100 °C

With mercury(II) cyanide; acetic acid; In acetonitrile;

DOI:10.1016/0008-6215(82)85025-8

upstream raw materials:

p-nitrophenyl 3-O-benzoyl-4,6-O-benzylidene-2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-mannopyranoside

p-nitrophenyl 3-O-benzoyl-4,6-O-benzylidene-α-D-mannopyranoside

3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide

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