5-AZIDO-5-DEOXY-3,4-DI-O-ACETYL-1,2-O-ISOPROPYLIDENE-BETA-D-FRUCTOSE

Base Information

• Chemical Name: 5-AZIDO-5-DEOXY-3,4-DI-O-ACETYL-1,2-O-ISOPROPYLIDENE-BETA-D-FRUCTOSE
• CAS No.: 94801-00-0
• Molecular Formula: C13H19 N3 O7
• Molecular Weight: 329.31
• Mol file: 94801-00-0.mol

Synonyms:1,3,6-Trioxaspiro[4.5]decane,b-D-fructopyranose deriv.

Chemical Property of 5-AZIDO-5-DEOXY-3,4-DI-O-ACETYL-1,2-O-ISOPROPYLIDENE-BETA-D-FRUCTOSE

Chemical Property:

• PSA: 130.04000
• LogP: 0.49086

Purity/Quality:

99%min ^*data from raw suppliers

3,4-Di-O-acetyl-5-azido-5-deoxy-1,2-O-isopropylidene-b-D-fructose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-AZIDO-5-DEOXY-3,4-DI-O-ACETYL-1,2-O-ISOPROPYLIDENE-BETA-D-FRUCTOSE

There total 1 articles about 5-AZIDO-5-DEOXY-3,4-DI-O-ACETYL-1,2-O-ISOPROPYLIDENE-BETA-D-FRUCTOSE 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: 74.0%

Acetic acid (8S,9S,10S)-9-acetoxy-2,2-dimethyl-8-(toluene-4-sulfonyloxy)-1,3,6-trioxa-spiro[4.5]dec-10-yl ester (53821-66-2) → Acetic acid (8R,9R,10S)-9-acetoxy-8-azido-2,2-dimethyl-1,3,6-trioxa-spiro[4.5]dec-10-yl ester (94801-00-0)

Guidance literature:

With lithium azide; In N,N-dimethyl-formamide; at 70 ℃; for 72h;

DOI:10.1021/jo00206a037

Reference yield:

Acetic acid (8R,9R,10S)-9-acetoxy-8-azido-2,2-dimethyl-1,3,6-trioxa-spiro[4.5]dec-10-yl ester (94801-00-0) → 2,5-dideoxy-2,5-imino-D-mannitol (59920-31-9)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOCH₃ / methanol / 1 h / Ambient temperature

2: 93 percent / H₂O, Biol-Rad AG 50W-X₈ (hydrogen form) / ethanol / 2 h / 45 °C

3: 100 percent / H₂ / 10percent Pd/C / ethanol / 1292.9 Torr

With Biol-Rad AG 50W-X₈ (hydrogen form); water; hydrogen; sodium methylate; palladium on activated charcoal; In methanol; ethanol;

DOI:10.1021/jo00206a037

Reference yield:

Acetic acid (8R,9R,10S)-9-acetoxy-8-azido-2,2-dimethyl-1,3,6-trioxa-spiro[4.5]dec-10-yl ester (94801-00-0) → 5-azido-5-deoxy-D-fructopyranose (94801-02-2)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOCH₃ / methanol / 1 h / Ambient temperature

2: 93 percent / H₂O, Biol-Rad AG 50W-X₈ (hydrogen form) / ethanol / 2 h / 45 °C

With Biol-Rad AG 50W-X₈ (hydrogen form); water; sodium methylate; In methanol; ethanol;

DOI:10.1021/jo00206a037

upstream raw materials:

Acetic acid (8S,9S,10S)-9-acetoxy-2,2-dimethyl-8-(toluene-4-sulfonyloxy)-1,3,6-trioxa-spiro[4.5]dec-10-yl ester

Downstream raw materials:

2,5-dideoxy-2,5-imino-D-mannitol

5-azido-5-deoxy-D-fructopyranose

Refernces