(2S,3R,4R,5R)-2-Methyl-6-phenylamino-tetrahydro-pyran-3,4,5-triol

Base Information

• Chemical Name: (2S,3R,4R,5R)-2-Methyl-6-phenylamino-tetrahydro-pyran-3,4,5-triol
• CAS No.: 27136-83-0
• Molecular Formula: C₁₂H₁₇NO₄
• Molecular Weight: 239.271
• Mol file: 27136-83-0.mol

Synonyms:(2S,3R,4R,5R)-2-Methyl-6-phenylamino-tetrahydro-pyran-3,4,5-triol

Chemical Property of (2S,3R,4R,5R)-2-Methyl-6-phenylamino-tetrahydro-pyran-3,4,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,5R)-2-Methyl-6-phenylamino-tetrahydro-pyran-3,4,5-triol

There total 1 articles about (2S,3R,4R,5R)-2-Methyl-6-phenylamino-tetrahydro-pyran-3,4,5-triol 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: 96.0%

L-rhamnose (73-34-7) + aniline (62-53-3) → (2S,3R,4R,5R)-2-Methyl-6-phenylamino-tetrahydro-pyran-3,4,5-triol (27136-83-0)

Guidance literature:

In ethanol; at 20 ℃; for 12h;

DOI:10.1016/j.tetlet.2006.07.024 DOI:10.1016/j.tetlet.2007.11.057

Reference yield: 85.0%

(2S,3R,4R,5R)-2-Methyl-6-phenylamino-tetrahydro-pyran-3,4,5-triol (27136-83-0) + acetic anhydride (108-24-7) → Acetic acid (3R,4R,5S,6S)-4,5-diacetoxy-6-methyl-2-phenylamino-tetrahydro-pyran-3-yl ester (913057-17-7)

Guidance literature:

With pyridine; at 0 - 4 ℃; for 12h;

DOI:10.1016/j.tetlet.2006.07.024

Reference yield:

(2S,3R,4R,5R)-2-Methyl-6-phenylamino-tetrahydro-pyran-3,4,5-triol (27136-83-0) → 3,3-bis(4-methylphenyl)-1-(β-L-rhamnopyranosyl)indolin-2-one (1629138-88-0)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 24 h / 0 °C

2: aluminum (III) chloride / 1.5 h / 55 °C

3: aluminum (III) chloride / 3 h / 80 °C / Inert atmosphere

4: sodium methylate / methanol / 12 h / 20 °C / Inert atmosphere

With pyridine; aluminum (III) chloride; sodium methylate; In methanol;

DOI:10.1039/c4ra02627f

upstream raw materials:

L-rhamnose

aniline

Downstream raw materials:

Acetic acid (3R,4R,5S,6S)-4,5-diacetoxy-6-methyl-2-phenylamino-tetrahydro-pyran-3-yl ester

1-(2,3,4-tri-O-acetyl-β-L-rhamnopyranosyl)-3,3-diphenylindolin-2-one

3,3-diphenyl-1-(β-L-rhamnopyranosyl)indolin-2-one

3,3-bis(4-methylphenyl)-1-(β-L-rhamnopyranosyl)indolin-2-one