(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(phenylamino)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

• Chemical Name: (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(phenylamino)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS No.: 42891-46-3
• Molecular Formula: C₂₀H₂₅NO₉
• Molecular Weight: 423.42
• Mol file: 42891-46-3.mol

Synonyms:(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(phenylamino)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property of (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(phenylamino)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(phenylamino)tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 7 articles about (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(phenylamino)tetrahydro-2H-pyran-3,4,5-triyl triacetate 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: 85.0%

2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine (41355-50-4,51642-81-0,58484-22-3,70128-27-7,70145-20-9,94482-21-0,98300-76-6) + phenylboronic acid (98-80-6) → (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(phenylamino)tetrahydro-2H-pyran-3,4,5-triyl triacetate (42891-46-3)

Guidance literature:

With pyridine; copper diacetate; In dichloromethane; at 20 ℃; for 24h; Reagent/catalyst;

DOI:10.1039/c3cc44780d

Reference yield:

acetic anhydride (108-24-7) → (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(phenylamino)tetrahydro-2H-pyran-3,4,5-triyl triacetate (42891-46-3) + tetra-O-acetyl-N-phenyl-α-D-glucopyranosylamine (3945-14-0)

Guidance literature:

With pyridine;

DOI:10.1039/jr9500000967 DOI:10.1021/ja01110a047

Reference yield:

β-D-glucose (492-61-5) → (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(phenylamino)tetrahydro-2H-pyran-3,4,5-triyl triacetate (42891-46-3)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol / 78 °C

2: pyridine / 0 °C

With pyridine; In ethanol;

DOI:10.1039/c3ob40603b

upstream raw materials:

aniline

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

tetra-O-acetyl-N-phenyl-α-D-glucopyranosylamine

acetic anhydride

Downstream raw materials:

C₃₄H₃₈NO₁₁P