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{"id":94,"date":"2012-07-30T13:56:31","date_gmt":"2012-07-30T13:56:31","guid":{"rendered":"http:\/\/amcrasto.theeurekamoments.com\/?p=94"},"modified":"2012-07-30T13:57:59","modified_gmt":"2012-07-30T13:57:59","slug":"efficient-levoglucosenone-production","status":"publish","type":"post","link":"https:\/\/amcrasto.theeurekamoments.com\/2012\/07\/30\/efficient-levoglucosenone-production\/","title":{"rendered":"Efficient levoglucosenone production"},"content":{"rendered":"

Levoglucosenone<\/h3>\n

Levoglucosenone is a highly dehydrated sugar that has been used in the preparation of chiral synthons such as (\u2013)-y-multistriatin and (+)-Prelog\u2014Djerassi lactonic acid.<\/p>\n

Negative-form is a pyrolysis product of cellulose and cellulose-containing materials including pulp and paper waste products. Known as a pyrolytic product of cellulose, which is very useful as a chiral source for synthesizing natural products.<\/p>\n

\"\"<\/p>\n

Levoglucosenone<\/h1>\n\n\n\n\n
Density<\/th>\n1.29 g\/mL<\/td>\n<\/tr>\n
Boiling Point<\/th>\n57-57.5 \u00b0C \/ 0.5 mm<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n\n\n\n
\n\n\n\n\n\n\n\n\n\n
CAS No:<\/td>\n\n
37112-31-5<\/strong><\/div>\n<\/td>\n<\/tr>\n
Synonyms:<\/p>\n
1,6-Anhydro-3,4-dideoxy-a-D-glycero-hex-3-enopyranose-2-ulose
\n(1S,5R)-6,8-Dioxobicyclo[3.2.1]oct-2-en-4-one<\/strong><\/div>\n<\/td>\n<\/tr>\n
Solubility:<\/td>\nSoluble in Chloroform<\/td>\n<\/tr>\n
Physical Appearance:<\/td>\nColorless to Yellow Oil<\/td>\n<\/tr>\n
Chemical Formula:<\/td>\n\n
\n
C<\/span>6<\/span><\/sub>H<\/span>6<\/span><\/sub>O<\/span>3<\/span><\/sub><\/div>\n<\/div>\n<\/td>\n<\/tr>\n
Molecular Weight:<\/td>\n\n
126.11<\/strong><\/div>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<\/td>\n
<\/td>\n<\/tr>\n
\n\n\n\n
References:<\/p>\n
1. Shafizadeh F, Furneaux R, Stevenson T, Carbohydr. Res. 1979 and Essig, M.G., et al.: Carbohydr. Res., 156, 225 (1986)<\/div>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

also Taniguchi, T., et al.: Synlett, 971 (1996),<\/p>\n

\n

Efficient levoglucosenone production<\/h1>\n<\/div>\n
Shinji Kudo ,\u00a0 et al, Green Chem.<\/strong><\/em>, 2011,13<\/strong>, 3306-3311<\/div>\n

DOI: <\/strong> 10.1039\/C1GC15975E<\/p>\n

http:\/\/pubs.rsc.org\/en\/Content\/ArticleLanding\/2011\/GC\/c1gc15975e\u00a0\u00a0\u00a0 COPY PASTE LINK<\/p>\n

\"Graphical<\/div>\n
<\/div>\n
<\/div>\n
Levoglucosenone is a synthetically valuable and versatile compound that is present as a minor product of cellulose pyrolysis. Here, the paper\u00a0 reports the catalytic pyrolysis of cellulose by mixing with 1-butyl-2,3-dimethylimidazolium triflate ionic liquid (IL), forming levoglucosenone in high yield. The catalysis of the IL was selectively directed to form levoglucosenone, while the low content of IL (50%) effectively prevented formation of char, leading to a yield near 20% even at 250 \u00b0C. The thermally stable IL could be fully recovered from the mixture pyrolyzed up to 300 \u00b0C and reutilized for pyrolysis.<\/div>\n

\"\"<\/p>\n

\"Levoglucosenone\"<\/p>\n

See papers on levoglucosenone:<\/strong>
\n(1S,5R)-6,8-Dioxabicyclo[3.2.1]oct-2-en-4-one<\/span>
\nM.S.Miftakhov, et al.
\nLevoglucosenone: the properties, reactions, and use in fine organic synthesis
\n Russ.Chem.Rev., 1994, 63 (10), 869-882 <\/a><\/p>\n

Herdewijn P, et al.
\n3′-substituted 2′,3′-dideoxynucleoside analogues as potential anti-HIV (HTLV-III\/LAV) agents
\n
J.Med.Chem., 1987, 30(8), 1270-1278 <\/a><\/p>\n

M.Jung and M.Kiankarimi
\nSynthesis of Methylene-Expanded 2′,3′-Dideoxyribonucleosides
\n
J.Org.Chem., 1998, 63 (23), 8133-8144 <\/a><\/p>\n

http:\/\/levoglucosenone.com\/derivatives\/\u00a0\u00a0\u00a0\u00a0 COPY PASTE LINK<\/p>\n

 <\/p>\n","protected":false},"excerpt":{"rendered":"

Levoglucosenone Levoglucosenone is a highly dehydrated sugar that has been used in the preparation of chiral synthons such as (\u2013)-y-multistriatin and (+)-Prelog\u2014Djerassi lactonic acid. Negative-form is a pyrolysis product of cellulose and cellulose-containing materials including pulp and paper waste products. Known as a pyrolytic product of cellulose, which is very useful as a chiral source… Continue reading Efficient levoglucosenone production<\/span><\/a><\/p>\n","protected":false},"author":1,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[3,4],"tags":[143,144],"_links":{"self":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/94"}],"collection":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/comments?post=94"}],"version-history":[{"count":2,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/94\/revisions"}],"predecessor-version":[{"id":96,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/posts\/94\/revisions\/96"}],"wp:attachment":[{"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/media?parent=94"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/categories?post=94"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/amcrasto.theeurekamoments.com\/wp-json\/wp\/v2\/tags?post=94"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}