1,2-O-Isopropylidene-5-keto-α-D-glucose

Base Information

• Chemical Name: 1,2-O-Isopropylidene-5-keto-α-D-glucose
• CAS No.: 19684-32-3
• Molecular Formula: C₉H₁₄O₆
• Molecular Weight: 218.207
• Mol file: 19684-32-3.mol

Synonyms:1,2-O-isopropylidene-α-D-xylo-hexafuranos-5-ulose

Chemical Property of 1,2-O-Isopropylidene-5-keto-α-D-glucose

Chemical Property:

Purity/Quality:

1,2-O-Isopropylidene-5-keto-α-D-glucose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1,2-O-Isopropylidene-5-keto-α-D-glucose is a reactant used in organic synthesis of D-glucose derivatives as potential antimalarial agents and inhibitors of several glucosidases.

Technology Process of 1,2-O-Isopropylidene-5-keto-α-D-glucose

There total 4 articles about 1,2-O-Isopropylidene-5-keto-α-D-glucose 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: 98.0%

1,2-O-isopropylidene-α-D-glucofuranose (18549-40-1) → 1,2-O-isopropylidene-α-D-xylo-hexafuranos-5-ulose (19684-32-3)

Guidance literature:

1,2-O-isopropylidene-α-D-glucofuranose; With bis(tri-n-butyltin)oxide; In chloroform; for 1h; Reflux; Molecular sieve;

With bromine; for 0.0833333h; Cooling with ice;

Reference yield: 5.0%

1,2-O-isopropylidene-α-D-glucofuranose (18549-40-1) → 1,2-O-isopropylidene-α-D-xylo-hexafuranos-5-ulose (19684-32-3) + 1,2-O-isopropylidene-α-D-ribo-hexafuranos-3-ulose (93688-68-7)

Guidance literature:

With bromine; In water; for 7h; Title compound not separated from byproducts; Ambient temperature; pH= 7.0;

DOI:10.1016/0008-6215(80)90006-3

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 1,2-O-isopropylidene-α-D-xylo-hexafuranos-5-ulose (19684-32-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: acetic acid; water / 8 h / 20 °C

2.1: N-Bromosuccinimide; di(n-butyl)tin oxide / methanol / 2 h / Reflux

2.2: 0.33 h

With N-Bromosuccinimide; water; di(n-butyl)tin oxide; acetic acid; In methanol;

DOI:10.1002/ejoc.201300720

upstream raw materials:

1,2-O-isopropylidene-α-D-glucofuranose

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

methyl 5-deoxy-2,3-O-(1-methylethylidene)-β-D-ribo-hexofuranoside

9-(5-Desoxy-β-D-ribo-hexofuranosyl)adenin

Acetic acid (3aR,6S,6aR)-5-((R)-1,2-diacetoxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Refernces

• 1、 -. "N-aryl-1-deoxynojirimycin derivative and application thereof in preparing of medicine for treating diabetes". Paragraph 0056-0058; 0074; 0075; 0089; 0090; 0111; 0112. . Retrieved 2017/07/18.
• 2、 Robins,Guo,Wnuk. "Elimination of chlorine (radical) or tosylate (anion) from C2' of nucleoside C3' free radicals as model reactions postulated to occur at the active site of ribonucleotide reductases". . p. 3637 - 3638. Retrieved 2007/10/03.