phenyl 3,6-di-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-allopyranoside

Base Information

• Chemical Name: phenyl 3,6-di-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-allopyranoside
• CAS No.: 146691-47-6
• Molecular Formula: C₄₄H₄₂N₂O₁₇S
• Molecular Weight: 902.887
• Mol file: 146691-47-6.mol

Synonyms:phenyl 3,6-di-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-allopyranoside

Chemical Property of phenyl 3,6-di-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-allopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 3,6-di-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-allopyranoside

There total 4 articles about phenyl 3,6-di-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-allopyranoside 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: 90.0%

phenylthiotrimethylsilane (4551-15-9) + 1,3,6-tri-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranose (160066-96-6) → phenyl 3,6-di-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-allopyranoside (146691-47-6)

Guidance literature:

With zinc(II) iodide; In 1,2-dichloro-ethane; for 4h; Ambient temperature;

DOI:10.1246/bcsj.67.2888

Reference yield:

3,6-di-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranose (160066-97-7) → phenyl 3,6-di-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-allopyranoside (146691-47-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / NaOAc / aq. acetic acid / 4 h / 70 °C

2: 90 percent / ZnI₂ / 1,2-dichloro-ethane / 4 h / Ambient temperature

With sodium acetate; zinc(II) iodide; In acetic acid; 1,2-dichloro-ethane;

DOI:10.1246/bcsj.67.2888

Reference yield:

allyl 3,6-di-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranoside (160066-94-4) → phenyl 3,6-di-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-1-thio-β-D-allopyranoside (146691-47-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / NaOAc, PdCl₂ / aq. acetic acid / 2 h / 50 °C

2: 86 percent / NaOAc / aq. acetic acid / 4 h / 70 °C

3: 90 percent / ZnI₂ / 1,2-dichloro-ethane / 4 h / Ambient temperature

With sodium acetate; zinc(II) iodide; palladium dichloride; In acetic acid; 1,2-dichloro-ethane;

DOI:10.1246/bcsj.67.2888

upstream raw materials:

acetic anhydride

phenylthiotrimethylsilane

1,3,6-tri-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranose

3,6-di-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-allopyranosyl)-2-deoxy-2-phthalimido-β-D-allopyranose