3-O-trityl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-arabinopyranose

Base Information

• Chemical Name: 3-O-trityl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-arabinopyranose
• CAS No.: 105313-37-9
• Molecular Formula: C₂₇H₂₅NO₅
• Molecular Weight: 443.499
• Mol file: 105313-37-9.mol

Synonyms:3-O-trityl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-arabinopyranose

Chemical Property of 3-O-trityl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-arabinopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-trityl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-arabinopyranose

There total 4 articles about 3-O-trityl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-arabinopyranose 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: 56.0%

triphenylmethyl perchlorate + 1,2-O-<1-(exo-cyano)ethylidene>-β-l-arabinopyranose (105313-35-7) → 3-O-trityl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-arabinopyranose (105313-37-9) + 4-O-trityl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-arabinopyranose (105313-36-8)

Guidance literature:

With 2,4,6-trimethyl-pyridine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1007/BF00952870

Reference yield:

bromo-2,3,4-O-triacetyl-α/β-L-arabinopyranoside (51830-02-5) → 3-O-trityl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-arabinopyranose (105313-37-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 2.64 g / Bu₄NBr / acetonitrile / 65 h

2: 81 percent / MeONa / methanol / 0.5 h / 20 °C

3: 17.5 percent / 2,4,6-collidine / CH₂Cl₂ / 1 h / 20 °C

With 2,4,6-trimethyl-pyridine; tetrabutylammomium bromide; sodium methylate; In methanol; dichloromethane; acetonitrile;

DOI:10.1007/BF00952870

Reference yield:

1,2,3,4-tetra-O-acetyl-L-arabinopyranose (1233-03-0,2595-11-1,4026-34-0,4049-33-6,4049-34-7,4257-95-8,4257-98-1,4258-00-8,4627-30-9,17080-99-8,19186-37-9,25227-11-6,25243-38-3,62446-93-9,62929-49-1,67226-03-3,78087-60-2,78088-17-2,82890-16-2,86782-34-5,86782-35-6,92218-63-8,99880-95-2,108646-05-5,115939-79-2,142130-89-0,123163-97-3) → 3-O-trityl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-arabinopyranose (105313-37-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / HBr / acetic acid / 1.5 h

2: 2.64 g / Bu₄NBr / acetonitrile / 65 h

3: 81 percent / MeONa / methanol / 0.5 h / 20 °C

4: 17.5 percent / 2,4,6-collidine / CH₂Cl₂ / 1 h / 20 °C

With 2,4,6-trimethyl-pyridine; tetrabutylammomium bromide; hydrogen bromide; sodium methylate; In methanol; dichloromethane; acetic acid; acetonitrile;

DOI:10.1007/BF00952870

upstream raw materials:

1,2-O-<1-(exo-cyano)ethylidene>-β-l-arabinopyranose

bromo-2,3,4-O-triacetyl-α/β-L-arabinopyranoside

1,2,3,4-tetra-O-acetyl-L-arabinopyranose

3,4-di-O-acetyl-1,2-O-<(1-exo-cyano)ethylidene>-β-L-arabinopyranose

Downstream raw materials:

4-O-acetyl-3-O-trityl-1,2-O-<1-(exo-cyano)ethylidene>-β-L-arabinopyranose