2,3,4,6-TETRA-O-ACETYL LINAMARIN

Base Information

• Chemical Name: 2,3,4,6-TETRA-O-ACETYL LINAMARIN
• CAS No.: 66432-53-9
• Molecular Formula: C18H25NO10
• Molecular Weight: 415.397
• Mol file: 66432-53-9.mol

Synonyms:2-(2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYLOXY)ISOBUTYRONITRILE;2,3,4,6-TETRA-O-ACETYL LINAMARIN;2-(2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyloxy)isobutyronitrile;2-(2,3,4,6-Tetra-O-acetyl--D-glucopyranosyloxy)isobutyronitrile;LinaMarin Tetraacetate

Chemical Property of 2,3,4,6-TETRA-O-ACETYL LINAMARIN

Chemical Property:

• Melting Point: 140-141°C
• Boiling Point: 484.4±45.0 °C(Predicted)
• PSA: 147.45000
• Density: 1.26±0.1 g/cm3(Predicted)
• LogP: 0.38828
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform, Ethyl Acetate

Purity/Quality:

98% ^*data from raw suppliers

2,3,4,6-Tetra-O-acetyl Linamarin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2,3,4,6-Tetra-O-acetyl Linamarin (cas# 66432-53-9) is a compound useful in organic synthesis.

Technology Process of 2,3,4,6-TETRA-O-ACETYL LINAMARIN

There total 5 articles about 2,3,4,6-TETRA-O-ACETYL LINAMARIN 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: 93.0%

2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)isobutyramide (207512-69-4) → 2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)isobutyronitrile (66432-53-9)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃;

DOI:10.1016/S0040-4020(02)00304-6

Reference yield:

linamarin (554-35-8) + acetic anhydride (108-24-7) → 2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)isobutyronitrile (66432-53-9)

Guidance literature:

With pyridine; Ambient temperature;

DOI:10.1016/0031-9422(89)85023-X

Reference yield:

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate (74808-10-9) → 2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)isobutyronitrile (66432-53-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 31 percent / BF₃*Et₂O / CH₂Cl₂ / 1.) -50 deg C, 15 min,2.) -50 deg C to room temperature, 3 h

2: 1.) COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) -78 deg C, 15 min

With oxalyl dichloride; boron trifluoride diethyl etherate; dimethyl sulfoxide; triethylamine; In dichloromethane;

DOI:10.1271/bbb.62.453

upstream raw materials:

linamarin

acetic anhydride

2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)isobutyramide

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate

Downstream raw materials:

linamarin