884655-08-7Relevant academic research and scientific papers
Application of a tandem seleno-michael/aldol reaction in the total syntheses of (+)-Pericosine B, (+)-Pericosine C, (+)-COTC and 7-chloro-analogue of (+)-Gabosine C
Banachowicz, Piotr,Bidu?, Natalia,Buda, Szymon
, (2020/07/24)
Synthesis of (+)-Pericosine B, (+)-Pericosine C, (+)-COTC and a 7-chloro-analogue of (+)-Gabosine C was achieved via tandem seleno-Michael/aldol reactions as key steps. The carbasugar linear precursor was obtained from cheap and readily available D-ribose in 7 steps which included resolution of the D-ribopyranose and the D-ribofuranose forms. Further transformation of the cyclic product involving a regioselective Steglich esterification or methylation of the secondary hydroxyl group gave rise to protected (+)-COTC, (+)-Pericosine B and (+)-Pericosine C. Deprotection of benzyl ethers at ?78 °C gave the titled compounds in satisfactory yields.
Divergent total synthesis of D-ribo-phytosphingosine and L-ribo-phytosphingosine from D-ribose
Chun, Jong Soo,Hong, Seung Min,Jeon, Tae Hong,Park, Sook Jin,Son, Han Pyo,Jung, Jun Min,Choi, Young Jae,Kim, In Su,Jung, Young Hoon
, p. 8550 - 8556 (2016/12/09)
Divergent total synthesis of D-ribo-phytosphingosine (1) and L-ribo-phytosphingosine (2) was achieved from readily available D-ribose via cross-metathesis reaction, Wittig reaction, and diastereoselective amination reaction of allylic ethers using chlorosulfonyl isocyanate (CSI) as the key steps. As results, reactions of anti-1,2-dibenzyl ethers 11 and 16 with chlorosulfonyl isocyanate afforded exclusively anti-1,2-amino alcohols 12 and 17 with diastereoselectivity of 32:1 and 31:1 in 75% and 76% yields, respectively. These results could be explained by the neighboring group effect, leading to retention of stereochemistry.
Regioselective and diastereoselective amination of polybenzyl ethers using chlorosulfonyl isocyanate: Total syntheses of 1,4-dideoxy-1,4-imino-D-arabinitol and (-)-lentiginosine
Kim, In Su,Zee, Ok Pyo,Jung, Young Hoon
, p. 4101 - 4104 (2007/10/03)
The total syntheses of DAB1 (1) and (-)-lentiginosine (2) were concisely accomplished from D-lyxose via regioselective and diastereoselective NHCbz introduction using CSI, chemoselective removal of the Cbz protection, and ring-closing metathesis as key steps.
Stereoselective C-glycosylation reactions of pyranoses: The conformational preference and reactions of the mannosyl cation
Lucero, Claudia G.,Woerpel
, p. 2641 - 2647 (2007/10/03)
A systematic study of C-glycosylations of acetals related to mannose and other pyranoses was conducted. The C-5 alkoxyalkyl group provides only a modest influence on stereoselectivity. On the other hand, studies of pentopyranoses bearing alkoxy groups at
