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

Base Information

• Chemical Name: 2-[(2S,3R,4R,5S,6R)-4,5-Dihydroxy-6-hydroxymethyl-2-(4-nitro-phenylsulfanyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione
• CAS No.: 780804-37-7
• Molecular Formula: C₂₀H₁₈N₂O₈S
• Molecular Weight: 446.438
• Mol file: 780804-37-7.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

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

Reference yield:

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) → 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 (249552-07-6)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 3 h / 20 °C

2: 74 percent / N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / 0.92 h / -30 °C

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; 1: Substitution / 2: Condensation;

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

Reference yield:

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

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 3 h / 20 °C

2: 74 percent / N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂ / 0.92 h / -30 °C

3: 100 percent / pyridine / 2 h / 20 °C

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; 1: Substitution / 2: Condensation / 3: Acetylation;

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

upstream raw materials:

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

Downstream raw materials:

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