2-O,3-O:5-O,6-O-Bis(isopropylidene)-α-D-mannofuranosyl cyanide

Base Information

• Chemical Name: 2-O,3-O:5-O,6-O-Bis(isopropylidene)-α-D-mannofuranosyl cyanide
• CAS No.: 130468-52-9
• Molecular Formula: C13H19NO5
• Molecular Weight: 269.29366
• Mol file: 130468-52-9.mol

Synonyms:2-O,3-O:5-O,6-O-Bis(isopropylidene)-α-D-mannofuranosyl cyanide

Chemical Property of 2-O,3-O:5-O,6-O-Bis(isopropylidene)-α-D-mannofuranosyl 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:5-O,6-O-Bis(isopropylidene)-α-D-mannofuranosyl cyanide

There total 3 articles about 2-O,3-O:5-O,6-O-Bis(isopropylidene)-α-D-mannofuranosyl 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:

2,3:5,6-di-O-isopropylidene-α-D-mannofuranose (14131-84-1) → 2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyl cyanide (130468-52-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 56 percent / 2-fluoro-1-methylpyridinium tosylate, NEt₃ / CH₂Cl₂ / 91 h / Ambient temperature

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

With 1-methyl-2-fluoropyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00002a007

Reference yield:

diethylaluminium cyanide (5804-85-3) + 2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyl fluoride (96089-62-2) → 2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyl cyanide (130468-52-9) + 2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl cyanide (130468-51-8) + 2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyl isocyanide (130468-54-1) + 2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl isocyanide (130468-53-0)

Guidance literature:

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

DOI:10.1021/jo00002a007

Reference yield:

diethylaluminium cyanide (5804-85-3) + (3aS,4R,6R,6aS)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-fluoro-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxole (94898-41-6) → 2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyl cyanide (130468-52-9) + 2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl cyanide (130468-51-8) + 2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyl isocyanide (130468-54-1) + 2,3:5,6-di-O-isopropylidene-α-D-mannofuranosyl isocyanide (130468-53-0)

Guidance literature:

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

DOI:10.1021/jo00002a007

upstream raw materials:

diethylaluminium cyanide

2,3:5,6-di-O-isopropylidene-β-D-mannofuranosyl fluoride

(3aS,4R,6R,6aS)-4-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-6-fluoro-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxole

2,3:5,6-di-O-isopropylidene-α-D-mannofuranose