6-AMINO-6-DEOXY-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE HYDROCHLORIDE

Base Information

• Chemical Name: 6-AMINO-6-DEOXY-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE HYDROCHLORIDE
• CAS No.: 24384-87-0
• Molecular Formula: C9H17 N O5
• Molecular Weight: 219.238
• Mol file: 24384-87-0.mol

Synonyms:Glucofuranose,6-amino-6-deoxy-1,2-O-isopropylidene-, a-D- (8CI); Furo[2,3-d]-1,3-dioxole, a-D-glucofuranose deriv.

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

Chemical Property:

• Melting Point: 127-129 °C(Solv: ethyl acetate (141-78-6))
• Boiling Point: 420.0±40.0 °C(Predicted)
• PKA: 11.93±0.35(Predicted)
• PSA: 94.17000
• Density: 1.302±0.06 g/cm3(Predicted)
• LogP: 0.04560

Purity/Quality:

98%Min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 14 articles about 6-AMINO-6-DEOXY-1,2-O-ISOPROPYLIDENE-ALPHA-D-GLUCOFURANOSE HYDROCHLORIDE 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%

3,5-di-O-acetyl-6-deoxy-1,2-O-isopropylidene-6-azido-α-D-glucofuranose (65371-16-6) → 6-amino-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose (24384-87-0)

Guidance literature:

With triphenylphosphine; In pyridine; at 20 ℃; for 48h;

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose (23558-05-6) → 6-amino-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose (24384-87-0)

Guidance literature:

Multi-step reaction with 2 steps

1: n-BuLi / tetrahydrofuran / 3 h / -78 °C

2: ammonium formate / Pd/C / methanol / 0.67 h / Heating

With n-butyllithium; ammonium formate; palladium on activated charcoal; In tetrahydrofuran; methanol; 1: Henry reaction;

DOI:10.1016/j.carres.2006.02.007

Reference yield:

6-azido-3-O-benzyl-6-deoxy-1,2-O-(1-methylethylidene)-α-D-glucofuranose (23313-05-5) → 6-amino-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose (24384-87-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; for 12h; under 760 Torr; Ambient temperature;

DOI:10.1016/S0040-4039(98)01529-9

upstream raw materials:

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

O¹,O²-isopropylidene-6-nitro-6-deoxy-α-D-glucofuranose

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

6-azido-3-O-benzyl-6-deoxy-1,2-O-(1-methylethylidene)-α-D-glucofuranose

Downstream raw materials:

(6-Desoxy-1,2-O-isopropyliden-α-D-glucofuranos-6-yl)bis<3,6-didesoxy-3-(2,4-dinitroanilino)-1,2-O-isopropyliden-α-D-glucofuranos-6-yl>amin

1,6-dideoxy-1,6-imino-(2S,3R,4R,5R)-D-glucitol

6-deoxy-6-N-benzyloxycarbonyl-1,2-O-isopropylidene-3-O-phenylmethyl-α-D-gluco-1,4-furanose

Refernces

• 1、 Chakraborty, Chaitali,Dhavale, Dilip D.. "Short and efficient synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-tetrahydroxyazepanes via the Henry reaction". . p. 912 - 917. Retrieved 2007/10/03.
• 2、 Fuentes, Jose,Angulo, Manuel,Pradera, M. Angeles. "Completely regioselective synthesis of 5- and 6- amino and fluoro hexofuranoses via cyclic sulphates". . p. 7149 - 7152. Retrieved 2007/10/03.