Furo3,2-doxazol-6-ol, 5-(4R)-2,2-dimethyl-1,3-dioxolan-4-yl-3a,5,6,6a-tetrahydro-2-methyl-, (3aR,5S,6R,6aR)-

Base Information

• Chemical Name: Furo3,2-doxazol-6-ol, 5-(4R)-2,2-dimethyl-1,3-dioxolan-4-yl-3a,5,6,6a-tetrahydro-2-methyl-, (3aR,5S,6R,6aR)-
• CAS No.: 117177-19-2
• Molecular Formula: C11H17 N O5
• Molecular Weight: 243.26
• Mol file: 117177-19-2.mol

Synonyms:Furo3,2-doxazol-6-ol, 5-(4R)-2,2-dimethyl-1,3-dioxolan-4-yl-3a,5,6,6a-tetrahydro-2-methyl-, (3aR,5S,6R,6aR)-

Chemical Property of Furo3,2-doxazol-6-ol, 5-(4R)-2,2-dimethyl-1,3-dioxolan-4-yl-3a,5,6,6a-tetrahydro-2-methyl-, (3aR,5S,6R,6aR)-

Chemical Property:

• PSA: 69.51000
• LogP: -0.52350

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Furo3,2-doxazol-6-ol, 5-(4R)-2,2-dimethyl-1,3-dioxolan-4-yl-3a,5,6,6a-tetrahydro-2-methyl-, (3aR,5S,6R,6aR)-

There total 2 articles about Furo3,2-doxazol-6-ol, 5-(4R)-2,2-dimethyl-1,3-dioxolan-4-yl-3a,5,6,6a-tetrahydro-2-methyl-, (3aR,5S,6R,6aR)- 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: 71.0%

N-Acetyl-D-glucosamine (7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) + acetone (67-64-1) → 2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline (117177-19-2)

Guidance literature:

With iron(III) chloride;

DOI:10.1016/S0040-4039(00)79188-X

Reference yield:

2-acetamido-2-deoxy-D-glucose (7512-17-6,282727-46-2,478518-83-1,127959-06-2,78393-48-3) + acetone (67-64-1) → 2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline (117177-19-2)

Guidance literature:

With iron(III) chloride; for 0.3h; Inert atmosphere; Schlenk technique; Reflux;

DOI:10.1021/acs.orglett.5b02413

Reference yield: 81.0%

1,2,3,5-tetrafluorobenzene (2367-82-0) + 2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline (117177-19-2) → C17H18F3NO5

Guidance literature:

With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at 0 - 20 ℃; for 16h; regioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.5b02413

upstream raw materials:

N-Acetyl-D-glucosamine

acetone

2-acetamido-2-deoxy-D-glucose

Downstream raw materials:

methyl 2-acetamido-2-deoxy-5,6-O-isopropylidene-β-D-glucofuranoside

(R)-2-(((3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)propanoic acid

2-methyl-(3-O-benzyl-1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2.1-d>-2-oxazoline

N-acetyl-D-mannosamine

Refernces

• 1、 Furneaux,Lynch,Way,Winchester. "Synthesis of 2-acetamido-1,2,4-trideoxy-1,4-imino-D-galactitol, a new hexosaminidase inhibitor". . p. 3477 - 3480. Retrieved 1993.
• 2、 Henderson, Alexander S.,Medina, Sandra,Bower, John F.,Galan, M. Carmen. "Nucleophilic Aromatic Substitution (SNAr) as an Approach to Challenging Carbohydrate-Aryl Ethers". supporting information. p. 4846 - 4849. Retrieved 2015/10/12.
• 3、 -. "Novel O-acetylated decasaccharides". Page/Page column 27. . Retrieved 2011/12/01.