102919-04-0Relevant articles and documents
An efficient and green oxidation of vicinal diols to aldehydes using polymer-supported (diacetoxyiodo)benzene as the oxidant
Chen, Fen-Er,Xie, Bin,Zhang, Ping,Zhao, Jian-Feng,Wang, Hui,Zhao, Lei
, p. 619 - 622 (2007)
An operationally simple and clean oxidation of a variety of vicinal diols to aldehydes using polymer-supported (diacetoxyiodo)benzene (PSDIB) has been developed in high to excellent yields. Protecting groups such as OAc, OR, OBn, OBz and isopropylidene in the substrates were found to be stable under these reaction conditions. The regenerated PSDIB could be reused for the same reaction, affording oxidation products in high yield and purity. Georg Thieme Verlag Stuttgart.
Double reductive amination and selective strecker reaction of a D-lyxaric aldehyde: Synthesis of diversely functionalized 3,4,5-trihydroxypiperidines
Matassini, Camilla,Mirabella, Stefania,Goti, Andrea,Cardona, Francesca
, p. 3920 - 3924 (2012/09/08)
A D-mannose-derived aldehyde with the D-lyxo configuration is a versatile key intermediate to functionally and stereochemically diversified piperidines. It allowed the synthesis of natural 3,4,5-trihydroxypiperidines and new analogs through a double reductive amination strategy and the synthesis of novel 2-cyanotrihydroxypiperidines through a highly regio-and diastereoselective Strecker reaction.
Stereoselective syntheses of polyhydroxylated azepane derivatives from sugar-based epoxyamides. Part 1: Synthesis from d-mannose
Ona, Noe,Romero, Antonio,Assiego, Carmen,Bello, Claudia,Vogel, Pierre,Pino-Gonzalez, M. Soledad
scheme or table, p. 2092 - 2099 (2010/12/20)
An approach to the synthesis of polyhydroxyazepane derivatives from sugar-based epoxyamides or epoxyalcohols, in which the total regioselective epoxide opening by nitrogen nucleophiles is the key step, is described. Thus, novel polyhydroxyazepane carboxamides and aminomethyl polyhydroxyazepanes, with potential pharmacological interest, are synthesized from diacetone d-mannose. Configurational assignments of the obtained products were determined.
An improved synthesis of a key intermediate for (+)-biotin from d-mannose
Chen, Fen-Er,Zhao, Jian-Feng,Xiong, Fang-Jun,Xie, Bin,Zhang, Ping
, p. 2461 - 2464 (2008/02/12)
An efficient and reproducible process for the synthesis of methyl 2,3,4,5-tetradeoxy-7,8-O-isopropylidene-d-arabino-nanonate (2), a key intermediate in the total synthesis of (+)-biotin (1), starting from readily available d-mannose is described. The cruc
Chemoenzymatic synthesis of [3,9-13C]-labeled NeuAc and KDN
Sato, Ken-Ichi,Akai, Shoji,Hiroshima, Toshiyuki,Aoki, Hidenori,Sakuma, Mayumi,Suzuki, Ken-Ju
, p. 3513 - 3516 (2007/10/03)
The chemoenzymatic synthesis of 13C-labeled sialic acid (NeuAc) and 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) as useful molecular probes for studying the conformation of sialyl or KDN oligosaccharides attached to proteins was perform
Synthesis of new glycopeptides; application to the preparation of N-(5-enkephalyl)-α-D-galacto-oct-6-enopyranuronamide
Coutrot, Philippe,Grison, Claude,Lecouvey, Marc
, p. 27 - 46 (2007/10/03)
The synthesis of new glycopeptides in which the peptidic moiety is linked to the glucidic part through a keto α,β-ethylenic handle is described.Two routes have been studied.The first strategy devised uses Horner reagents derived from N-substituted (diethy
THE SYNTHESIS OF SOME SEVEN-CARBON SUGARS via THE OSMYLATION OF OLEFINIC SUGARS
Brimacombe, John S.,Kabir, Abul K. M. S.
, p. 35 - 52 (2007/10/02)
The stereochemical outcome of the catalytic osmylation of 6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-hept-6-enopyranose (10), 5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hex-5-enofuranose, (E)- and (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranose (20 and 27, respectively), methyl (Z)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hept-5-enofuranuronate (26), (E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-ribo-hept-5-enofuranose, benzyl (E)- and (Z)-5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-hept-5-enofuranoside (46 and 50, respectively), and methyluronate (49) has been examined.Such oxidations led to satisfactory syntheses of L-glycero-D-gluco-heptose and the corresponding heptitol (from 20), L-glycero-D-gulo-heptitol (from 26), D-glycero-D-gluco-heptitol (from 27), D-glycero-D-galacto-heptitol (from 10 and 46), (meso)-glycero-gulo-heptitol (from 49), and D-glycero-D-manno-heptitol (from 50).