2-O,3-O:4-O,6-O-Bis(isopropylidene)-β-D-mannopyranosyl cyanide

Base Information

• Chemical Name: 2-O,3-O:4-O,6-O-Bis(isopropylidene)-β-D-mannopyranosyl cyanide
• CAS No.: 130495-50-0
• Molecular Formula: C13H19NO5
• Molecular Weight: 269.29
• Mol file: 130495-50-0.mol

Synonyms:2-O,3-O:4-O,6-O-Bis(isopropylidene)-β-D-mannopyranosyl cyanide

Chemical Property of 2-O,3-O:4-O,6-O-Bis(isopropylidene)-β-D-mannopyranosyl cyanide

Chemical Property:

• PSA: 69.94000
• LogP: 0.94898

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O,3-O:4-O,6-O-Bis(isopropylidene)-β-D-mannopyranosyl cyanide

There total 4 articles about 2-O,3-O:4-O,6-O-Bis(isopropylidene)-β-D-mannopyranosyl cyanide 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: 8.0%

diethylaluminium cyanide (5804-85-3) + 2,3:4,6-di-O-isopropylidene-α-D-mannopyranosyl fluoride (130495-46-4) → 2,3:4,6-di-O-isopropylidene-β-D-mannopyranosyl cyanide (130495-50-0) + 2,3:4,6-di-O-isopropylidene-α-D-mannopyranosyl cyanide (130495-49-7) + 2,3:4,6-di-O-isopropylidene-β-D-mannopyranosyl isocyanide (130495-52-2) + 2,3:5,6-di-O-isopropylidene-α-D-mannopyranosyl isocyanide (130495-51-1)

Guidance literature:

In tetrahydrofuran; Yields of byproduct given; -3 deg C, 1h, then -> RT, 17h;

DOI:10.1021/jo00002a007

Reference yield: 4.5%

diethylaluminium cyanide (5804-85-3) + 2,3:4,6-di-O-isopropylidene-β-D-mannopyranosyl fluoride (130495-47-5) → 2,3:4,6-di-O-isopropylidene-β-D-mannopyranosyl cyanide (130495-50-0) + 2,3:4,6-di-O-isopropylidene-α-D-mannopyranosyl cyanide (130495-49-7) + 2,3:4,6-di-O-isopropylidene-β-D-mannopyranosyl isocyanide (130495-52-2) + 2,3:5,6-di-O-isopropylidene-α-D-mannopyranosyl isocyanide (130495-51-1)

Guidance literature:

In tetrahydrofuran; Yields of byproduct given; -3 deg C, 1h, then -> RT, 17h;

DOI:10.1021/jo00002a007

Reference yield:

D-Mannose (530-26-7) → 2,3:4,6-di-O-isopropylidene-β-D-mannopyranosyl cyanide (130495-50-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / p-toluenesulfonic acid monohydrate / dimethylformamide / 6 h / 0 °C

2: 13 percent / 2-fluoro-1-methylpyridinium tosylate, NEt₃ / CH₂Cl₂ / 91 h / Ambient temperature

3: tetrahydrofuran / -3 deg C, 1h, then -> RT, 17h

With 1-methyl-2-fluoropyridinium p-toluenesulfonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00002a007

upstream raw materials:

diethylaluminium cyanide

2,3:4,6-di-O-isopropylidene-β-D-mannopyranosyl fluoride

2,3:4,6-di-O-isopropylidene-α-D-mannopyranosyl fluoride

D-Mannose

Refernces