• Journal of the Korea Institute of Military Science and Technology
• /
• v.6 no.1
• /
• pp.108-115
• /
• 2003

TNAZ is a high explosive material because it is a highly strained ring compound containing one nitramine and gem dinditro groups. 1-t-butyl-3-nitroazetidine which was used as an intermediate previously, which declined the overall yield in synthesizing TNAZ. We obtained 1-t-butyl-3-hydroxymethyl-3-nitroazetidine in 64% yield from advances process which was used in synthesis of 1-t-butyl-3-nitroazetidine. The reaction pathway, shortening of reaction time, together with improvement of yield were studied too. We have obtained TNAZ in 85% yield.

• Polymer(Korea)
• /
• v.31 no.5
• /
• pp.417-421
• /
• 2007

A successful rapid synthesis of dendritic benzyl chlorides from dendritic benzyl alcohols using methanesulfonyl chloride/$Et_3N$ as activating agents was described. In this method, each dendritic benzyl chloride can be prepared in one pot: no isolation of intermediate mesylated dendrons is required. The key steps in the syntheses of dendritic benzyl chlorides were the mesylation of the hydroxymethyl group followed by the chlorination by in-situ generated triethylammonium chloride.

• The Journal of Natural Sciences
• /
• v.7
• /
• pp.47-51
• /
• 1995

In order to develope new asymmetric catalyst, we synthesized the following new sulfonamide derivatives start from S-Indoline-2-Carboxylic Acid via the following 5 steps. Hydroxy methyl derivative(1) was thus treated with methane sulfonyl chloride in the presence of triethylamine as base to give mesylated derivative(2) in 85% of isolated yield. The mesylate compound (2) was treated with excess sodium azide to give Azido derivative (4) in 95% isolated yield. Azido compound (3) was then reduced to the corresponding amino derivative in near quntitative yield by the hydrogenation under hydrogen atmospere in the presence of catalytic amount of Pd-C. The amino derivative (4) was converted to its sulfonamide derivatives by the treatment of compound(4) with triisopropyl benzene sulfonyl chloride in the presence of triethyl amine as base. Finally t-BOC group of the compound(5) was removed by the treatement of excess Trifluoro-acetic acid in near quantitative yield to give the target sulfonamide derivative (7) .in this paper we prepared compound(6) in 49% overall yield via the 5 steps of synthesis starting from t-Boc- 2-hydroxy methyl indoline(1) which cab be easily prepared from commercial available S-indoline-2-carboxylic acid by known methods. we plan to apply this new catalyst for the asymmetric reduction , diels-alder reaction, aldolcondensation reaction in due courses.

• Journal of the Korean Chemical Society
• /
• v.43 no.4
• /
• pp.447-455
• /
• 1999

Allyl (5R)-(Z)- and (5R)-(E)-6-[(2S)-2,3-isopropylidenedioxypropylidene]Penicillanate(10a and 10b) were prepared from allyl (5R)-dibromopenicillanate(6) via a sequence of reactions involving condensation with 2,3-O-isopropylidene-D-glyceraldehyde, reduction with $Zn-NH_4OAc$, and Mitsunobu elimination. Deprotection of isopropylidene and allyl groups of 10a gave potassium (5R)-(Z)-6-[(2S)-2,3-dihydroxypropylidene]penicillanate(4). However, deprotection of isopropylidene group of 10b afforded ${\alpha},\;{\beta}$-unsaturated-lactone(12). Allyl (5R)-(Z)- and (5R)-(E)-6-[(2S)-2-(t-butyldimethlsilyloxy)propylidene]penicillanate(18a and 18b) were prepared from ally (5R)-dibromopenicillanate(6) via a sequence of reactions involving condensation with (2S)-2-(t-butyldimethylsilyloxy)propanal(15), reduction with $Zn-NH_4OAc$ and Mitsunobu elimination or mesylation-elimination. Deprotection of t-butyldimethylsilyl and allyl groups of 18a and 18b gave potassium (5R)-(Z)- and (5R)-(E)-6-[(2S)-2-hydroxypropylidene]penicillanate(5a and 5b), respectively.