Skip to Content
Merck

Preparation of 6-azafulleroid-6-deoxy-2,3-di-O-myristoylcellulose.

Carbohydrate research (2011-09-17)
Nobuhiko Ichihara, Toshiyuki Takano, Keita Sakakibara, Hiroshi Kamitakahara, Fumiaki Nakatsubo
ABSTRACT

6-Azafulleroid-6-deoxy-2,3-di-O-myristoylcellulose (3) was synthesized from 6-azido-6-deoxycellulose (1) by two reaction steps. The myristoylation of compound 1 with myristoyl chloride/pyridine proceeded smoothly to give 6-azido-6-deoxy-2,3-di-O-myristoylcellulose (2) in 97.0% yield. The reaction of compound 2 with fullerene (C(60)) was carried out by microwave heating to afford compound 3 in high yield. It was found from FT-IR, (13)C NMR, UV-vis, differential pulse voltammetry (DPV), SEC analyses that compound 3 was the expected C(60)-containing polymer. Consequently, maximum degree of substitution of C(60) (DS(C60)) of compound 3 was 0.33.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Myristoyl chloride, 97%
Supelco
N,N-Dimethylacetamide, analytical standard
Sigma-Aldrich
N,N-Dimethylacetamide, ReagentPlus®, ≥99%
Sigma-Aldrich
N,N-Dimethylacetamide, anhydrous, 99.8%
Sigma-Aldrich
N,N-Dimethylacetamide, suitable for peptide synthesis, ≥99.8% (GC)
Sigma-Aldrich
N,N-Dimethylacetamide, suitable for HPLC, ≥99.9%
Sigma-Aldrich
N,N-Dimethylacetamide, puriss. p.a., ≥99.5% (GC)
Sigma-Aldrich
N,N-Dimethylacetamide, ReagentPlus®, 99%
Sigma-Aldrich
N,N-Dimethylacetamide, spectrophotometric grade, ≥99%