6-AZIDO-6-DEOXY-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE

Base Information

• Chemical Name: 6-AZIDO-6-DEOXY-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE
• CAS No.: 65371-16-6
• Molecular Formula: C9H15N3O5
• Molecular Weight: 245.23
• Hs Code.: 2940000080
• Mol file: 65371-16-6.mol

Synonyms:Glucofuranose,6-azido-6-deoxy-1,2-O-isopropylidene-, a-D- (6CI);

Chemical Property of 6-AZIDO-6-DEOXY-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE

Chemical Property:

• Appearance/Colour: White crystalline solid
• Melting Point: 101-103 °C
• PSA: 117.90000
• LogP: -0.65234
• Storage Temp.: -20°C Freezer

Purity/Quality:

98%Min ^*data from raw suppliers

6-Azido-6-deoxy-1,2-O-isopropylidene-a-D-glucofuranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-AZIDO-6-DEOXY-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE

There total 8 articles about 6-AZIDO-6-DEOXY-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE 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: 92.0%

6-deoxy-1,2-O-isopropylidene-6-(4'-methylbenzene)sulfonyloxy-D-glucofuranose (26275-20-7) → 3,5-di-O-acetyl-6-deoxy-1,2-O-isopropylidene-6-azido-α-D-glucofuranose (65371-16-6)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 40 ℃; for 15h;

DOI:10.1016/0040-4020(89)80060-2

Reference yield: 28.0%

6-Azido-6-desoxy-D-glucopyranose (20847-05-6,138332-00-0,138332-01-1) + acetone (67-64-1) → 6-Azido-6-desoxy-1,2:3,5-di-O-isopropyliden-α-D-glucofuranose (65371-17-7) + 3,5-di-O-acetyl-6-deoxy-1,2-O-isopropylidene-6-azido-α-D-glucofuranose (65371-16-6)

Guidance literature:

With hydrogenchloride; for 1.5h; Ambient temperature;

Reference yield:

1,2-O-isopropylidene-α-D-glucofuranose (18549-40-1) → 3,5-di-O-acetyl-6-deoxy-1,2-O-isopropylidene-6-azido-α-D-glucofuranose (65371-16-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / pyridine / 16 h / -15 °C

2: 92 percent / NaN₃ / dimethylformamide / 20 h / 120 °C

With pyridine; sodium azide; In N,N-dimethyl-formamide;

upstream raw materials:

1,2-O-isopropylidene-α-D-glucofuranos-6-yl methanesulfonate

6-deoxy-1,2-O-isopropylidene-6-(4'-methylbenzene)sulfonyloxy-D-glucofuranose

3-O-acetyl-6-azido-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose

6-Azido-6-desoxy-D-glucopyranose

Downstream raw materials:

6-amino-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose

6-Azido-6-desoxy-D-glucopyranose

6-azido-3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose

Refernces

• 1、 ?etin Telli, Fatma,Astley, Stephen Thomas,Salman, Azize Ye?im. "Synthesis, characterization, and antimicrobial activities of novel monosaccharide-containing Schiff base ligands". . p. 370 - 380. Retrieved 2017/07/04.
• 2、 Fernandez, Jose M. Garcia,Mellet, Carmen Ortiz,Maciejewski, Sylwester,Defaye, Jacques. "Thioureido-β-cyclodextrins as molecular carriers". . p. 2741 - 2742. Retrieved 2007/10/03.