4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxybenzonitrile

Base Information

• Chemical Name: 4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxybenzonitrile
• CAS No.: 74590-41-3
• Molecular Formula: C₁₃H₁₅NO₆
• Molecular Weight: 281.265
• Mol file: 74590-41-3.mol

Synonyms:4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxybenzonitrile

Chemical Property of 4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxybenzonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxybenzonitrile

There total 4 articles about 4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxybenzonitrile 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: 97.0%

p-cyanophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (74590-40-2) → 4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxybenzonitrile (74590-41-3)

Guidance literature:

sodium methylate; In methanol; for 4h; Ambient temperature;

DOI:10.1016/S0008-6215(00)85657-8

Reference yield:

4-cyanophenol (767-00-0) → 4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxybenzonitrile (74590-41-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 48 percent / zinc chloride / 0.5 h / 160 °C

2: 97 percent / sodium methoxide / methanol / 4 h / Ambient temperature

With zinc(II) chloride; sodium methylate; In methanol;

DOI:10.1016/S0008-6215(00)85657-8

Reference yield:

β-D-mannopyranose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → 4-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxybenzonitrile (74590-41-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 48 percent / zinc chloride / 0.5 h / 160 °C

2: 97 percent / sodium methoxide / methanol / 4 h / Ambient temperature

With zinc(II) chloride; sodium methylate; In methanol;

DOI:10.1016/S0008-6215(00)85657-8

upstream raw materials:

p-cyanophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

4-cyanophenol

β-D-mannopyranose pentaacetate

Downstream raw materials:

p-(aminomethyl)phenyl α-D-mannopyranoside