Convenient Large-Scale Synthesis of D-Glucaro-1,4:6,3-dilactone

被引:12
作者
Gehret, Troy C. [1 ]
Frobese, A. Stephen [1 ]
Zerbe, James S. [1 ]
Chenault, H. Keith [1 ]
机构
[1] EI DuPont Nemours & Co, Cent Res & Dev, Expt Stn, Wilmington, DE 19880 USA
关键词
HIV-1 PROTEASE INHIBITORS; RING-OPENING POLYADDITION; D-GLUCARIC ACID; ACTIVE POLYCONDENSATION; HYDROXYLATED NYLONS; MACROMOLECULAR-SYNTHESIS; HYDROPHILIC POLYAMIDE; GLUCOSACCHARIC ACID; SACCHARIC LACTONES; BETA-GLUCURONIDASE;
D O I
10.1021/jo9015985
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Calcium D-glucarate was converted into D-glucaro-1,4:6,3-dilactone on 32-g, 1-kg, and 22-kg scale, using azeotropic distillation with methyl isobutyl ketone to drive the dehydration. The crystalline product was >= 99.5% pure by GC and NMR, and overall yield was its high as 72%.
引用
收藏
页码:8373 / 8376
页数:4
相关论文
共 54 条
[1]   Design and fast synthesis of C-terminal duplicated potent C2-symmetric P1/P1′-modified HIV-1 protease inhibitors [J].
Alterman, M ;
Andersson, HO ;
Garg, N ;
Ahlsén, G ;
Lövgren, S ;
Classon, B ;
Danielson, UH ;
Kvarnström, I ;
Vrang, L ;
Unge, T ;
Samuelsson, B ;
Hallberg, A .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (19) :3835-3844
[2]   Design and synthesis of new potent C2-symmetric HIV-1 protease inhibitors.: Use of L-mannaric acid as a peptidomimetic scaffold [J].
Alterman, M ;
Björsne, M ;
Mühlman, A ;
Classon, B ;
Kvarnström, I ;
Danielson, H ;
Markgren, PO ;
Nillroth, U ;
Unge, T ;
Hallberg, A ;
Samuelsson, B .
JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (20) :3782-3792
[3]   POLYAMIDES CONTAINING CARBOHYDRATE RESIDUES [J].
BIRD, TP ;
BLACK, WAP ;
HARE, JB ;
DEWAR, ET .
JOURNAL OF THE CHEMICAL SOCIETY, 1963, (FEB) :1208-&
[4]   Synthesis and characterization of segmented hydrosoluble poly(tartaramide)s [J].
Bizzarri, R ;
Solaro, R ;
Chiellini, E .
JOURNAL OF BIOACTIVE AND COMPATIBLE POLYMERS, 1999, 14 (06) :504-517
[5]   OPTICALLY-ACTIVE POLYAMIDES DERIVED FROM L-TARTARIC ACID [J].
BOU, JJ ;
RODRIGUEZGALAN, A ;
MUNOZGUERRA, S .
MACROMOLECULES, 1993, 26 (21) :5664-5670
[6]  
Carter A, 2000, J POLYM SCI POL CHEM, V38, P3892, DOI 10.1002/1099-0518(20001101)38:21<3892::AID-POLA60>3.0.CO
[7]  
2-3
[8]   Synthesis of stereoregular head,tail hydroxylated nylons derived from D-glucose [J].
Chen, L ;
Kiely, DE .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (17) :5847-5851
[9]   D-GLUCARIC ACID ESTERS/LACTONES USED IN CONDENSATION POLYMERIZATION TO PRODUCE HYDROXYLATED NYLONS - A QUALITATIVE EQUILIBRIUM STUDY IN ACIDIC AND BASIC ALCOHOL-SOLUTIONS [J].
CHEN, L ;
KIELY, DE .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1994, 13 (04) :585-601
[10]   Macrocyclic inhibitors of the malarial aspartic proteases plasmepsin I, II, and IV [J].
Ersmark, K ;
Nervall, M ;
Gutiérrez-de-Terán, H ;
Hamelink, E ;
Janka, LK ;
Clemente, JC ;
Dunn, BM ;
Gogoll, A ;
Samuelsson, B ;
Åqvist, J ;
Hallberg, A .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (07) :2197-2208