4-nitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Base Information

• Chemical Name: 4-nitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside
• CAS No.: 212128-05-7
• Molecular Formula: C₂₆H₂₄N₂O₁₁S
• Molecular Weight: 572.549

Synonyms:4-nitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property of 4-nitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of 4-nitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside

There total 2 articles about 4-nitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 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: 91.0%

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose (10022-13-6) + para-nitrobenzenethiol (1849-36-1) → 4-nitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (212128-05-7)

Guidance literature:

With 4 Angstroem MS; In dichloromethane; at 0 ℃; for 4h;

DOI:10.1080/07328309808002341

Reference yield:

(+)-D-glucosamine hydrochloride (1078691-95-8) → 4-nitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (212128-05-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide / water monomer / 18 h / 20 °C

1.2: 3 h / 20 °C

2.1: boron trifluoride diethyl ether complex / dichloromethane / 15 h / 20 °C

With boron trifluoride diethyl ether complex; sodium hydroxide; In dichloromethane; water monomer;

DOI:10.1021/acs.joc.2c00184

Reference yield:

4-nitrophenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (212128-05-7) → 2-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-(4-nitro-phenylsulfanyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (780804-37-7)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 2h;

DOI:10.1016/S0008-6215(99)00080-4

upstream raw materials:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

para-nitrobenzenethiol

(+)-D-glucosamine hydrochloride

Downstream raw materials:

2-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-(4-nitro-phenylsulfanyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

4-nitrophenyl 2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-β-D-glucopyranoside

4-nitrophenyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1-> 4)-2-acetamido-6-O-tert-butyldiphenylsilyl-2-deoxy-1-thio-β-D-glucopyranoside

Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-(4-acetylamino-phenylsulfanyl)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester

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