𝔖 Bobbio Scriptorium
✦   LIBER   ✦

The chemistry of the 1-deoxynojirimycin system. Synthesis of 2-acetamido-1,2-dideoxynojirimycin from 1-deoxynojirimycin

✍ Scribed by Horst Böshagen; Fred-Robert Heiker; A. Matthias Schüller

Publisher
Elsevier Science
Year
1987
Tongue
English
Weight
569 KB
Volume
164
Category
Article
ISSN
0008-6215

No coin nor oath required. For personal study only.

✦ Synopsis

The synthesis of 2-acetamido-1 ,Zdideoxynojirimycin (Zacetamido-1,2,5-trideoxy-1,5-imino-D-glucitol) by a double inversion procedure starting from l-deoxynojirimycin is reported. The key intermediates were the selectively protected N-benzyl-l,5-dideoxy-l,5-imino-4,6-0-isopropylidene-~-mannitol, the triflate ester Nbenzyl -3 -0 -benzyl -1,5 -dideoxy -1.5 -imino -4,6 -0 -isopropylidene -2 -0 -(trifluoromethylsulfonyl)-D-mannitol, and 2-azido-N-benzyl-3 -0-benzyl-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol, readily obtained in a sequence from l-deoxynojirimycin. Thus I-deoxynojirimycin served as a synthon compatible with the basic operations of carbohydrate chemistry.

*Dedicated to my respected teacher Prof. Burckhardt Helferich on the occasion of his 100th anniversary.

📜 SIMILAR VOLUMES

A novel approach to the 1-deoxynojirimyc
A novel approach to the 1-deoxynojirimycin system: Synthesis from sucrose of 2-acetamido-1,2-dideoxynojirimycin, as well as some 2-N-modified derivatives
✍ Günther Gradnig; Günter Legler; Arnold E. Stütz 📂 Article 📅 1996 🏛 Elsevier Science 🌐 English ⚖ 502 KB

6-Azido-1,3,4-tri-O-benzyl-6-deoxy-D-fructofuranose can be easily obtained in two steps from the known 6,6'-diazido-6,6'-dideoxysucrose (available in two steps from sucrose) and cyclized by controlled hydrogenation and concomitant intramolecular reductive amination to give 3,4,6-tri-O-benzyl-1,5-did

ChemInform Abstract: The Synthesis of Es
ChemInform Abstract: The Synthesis of Ester and Ketone Analogues of 1-Deoxynojirimycin and Castanospermine.
✍ F. COMPERNOLLE; G. JOLY; K. PEETERS; S. TOPPET; G. HOORNAERT; A. KILONDA; BABADY 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 40 KB 👁 2 views

The Synthesis of Ester and Ketone Analogues of 1-Deoxynojirimycin and Castanospermine. -Biologically interesting analogues of the glucosidase inhibiting polyhydroxylated alkaloids 1-deoxynojirimycin, such as (XI) and (XII), and castanospermine, such as (XVI), (XVII), and (XVIII), are synthesized. -

ChemInform Abstract: Enantiopure 2,3-Dih
ChemInform Abstract: Enantiopure 2,3-Dihydro-4-pyridones as Synthetic Intermediates: Asymmetric Synthesis of 1-Deoxynojirimycin.
✍ Daniel L. Comins; Alan B. Fulp 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 31 KB 👁 2 views

## Abstract ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable v