N-Cbz-1,2:4,5-di-O-isopropylidene-3-amino-3-deoxy-β-D-fructopyranose

Base Information

• Chemical Name: N-Cbz-1,2:4,5-di-O-isopropylidene-3-amino-3-deoxy-β-D-fructopyranose
• CAS No.: 1224886-48-9
• Molecular Formula: C₂₀H₂₇NO₇
• Molecular Weight: 393.437
• Mol file: 1224886-48-9.mol

Synonyms:N-Cbz-1,2:4,5-di-O-isopropylidene-3-amino-3-deoxy-β-D-fructopyranose

Chemical Property of N-Cbz-1,2:4,5-di-O-isopropylidene-3-amino-3-deoxy-β-D-fructopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-Cbz-1,2:4,5-di-O-isopropylidene-3-amino-3-deoxy-β-D-fructopyranose

There total 2 articles about N-Cbz-1,2:4,5-di-O-isopropylidene-3-amino-3-deoxy-β-D-fructopyranose 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%

benzyl chloroformate (501-53-1,94274-21-2) + 1,2:4,5-di-O-isopropylidene-3-amino-3-deoxy-β-D-fructopyranose (402856-06-8) → N-Cbz-1,2:4,5-di-O-isopropylidene-3-amino-3-deoxy-β-D-fructopyranose (1224886-48-9)

Guidance literature:

With Amberlyst-15; at 20 ℃; for 0.25h; Neat (no solvent);

DOI:10.1080/00397911.2010.515341

Reference yield:

1,2:4,5-di-O-isopropylidene-3-deoxy-3-oxime-β-D-fructopyranose (402856-05-7) → N-Cbz-1,2:4,5-di-O-isopropylidene-3-amino-3-deoxy-β-D-fructopyranose (1224886-48-9)

Guidance literature:

Multi-step reaction with 2 steps

1: nickel(II) chloride hexahydrate; sodium tetrahydroborate / methanol / 8 h / -10 - 0 °C

2: dodecatungstophosphoric acid hydrate / dichloromethane / 0.17 h

With sodium tetrahydroborate; dodecatungstophosphoric acid hydrate; nickel(II) chloride hexahydrate; In methanol; dichloromethane;

DOI:10.1007/s12039-017-1237-y

Reference yield: 95.0%

N-Cbz-1,2:4,5-di-O-isopropylidene-3-amino-3-deoxy-β-D-fructopyranose (1224886-48-9) + methyl iodide (74-88-4) → C21H29NO7

Guidance literature:

N-Cbz-1,2:4,5-di-O-isopropylidene-3-amino-3-deoxy-β-D-fructopyranose; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.166667h;

methyl iodide; In N,N-dimethyl-formamide; for 2h;

DOI:10.1007/s12039-017-1237-y

upstream raw materials:

benzyl chloroformate

1,2:4,5-di-O-isopropylidene-3-amino-3-deoxy-β-D-fructopyranose

1,2:4,5-di-O-isopropylidene-3-deoxy-3-oxime-β-D-fructopyranose