3650-68-8

Usage

InChI:InChI=1/C10H22O4S2/c1-3-15-9(16-4-2)5-7(12)10(14)8(13)6-11/h7-14H,3-6H2,1-2H3/t7-,8-,10+/m1/s1

Upstream product

• 61-58-5 2-deoxy-D-arabino-hexopyranose 
• 75-08-1 ethanethiol 
• 13299-15-5 2-deoxy-D-glucose 
• 136770-90-6 tert-Butyl-((4R,4aS,6S,7aR)-6-ethoxy-2,2-dimethyl-tetrahydro-furo[3,2-d][1,3]dioxin-4-ylmethoxy)-dimethyl-silane 
• 13265-84-4 D-glucal 
• 154-17-6 D-2-deoxyglucose 

Downstream Products

• 73591-63-6 1,3-dideoxy-4,5:6,7-di-O-isopropylidene-D-arabino-heptulose (2,4-dinitrophenyl)hydrazone 
• 73591-60-3 1,3-dideoxy-4,5:6,7-di-O-isopropylidene-1-phenyl-D-arabino-heptulose diethyl dithioacetal 
• 144898-75-9 (3R,4S,5R)-3,4,5,6-Tetrakis-benzyloxy-hexanal 
• 192461-95-3 (11R),(12R)-dihydroxyeicosatrienoic acid 
• 50-00-0 formaldehyd 
• 64-18-6 formic acid 
• 136771-01-2 C₃₈H₄₆O₄S₂ 
• 106684-46-2 3.4.5-Tri-O-benzoyl-2-deoxy-6-O-trityl-D-arabinohexose-diaethyl-dithio-acetal 
• 901786-55-8 O³,O⁴,O⁵-triacetyl-O⁶-trityl-D-arabino-2-deoxy-hexose-diethyldithioacetal 
• 16885-34-0 3,4,5,6-tetra-O-acetyl-2-deoxy-D-arabino-hexose diethyl dithioacetal 

Relevant academic research and scientific papers

Versatility of the cyclo-oxymercuriation route to 1,2,4-Trioxanes

The versatility of the cyclo-oxymercuriation route to 1,2,4-trioxanes is illustrated by preparing with heterocyclic, unsaturated and carbohydrate substituents and by post-cyclisation modification of the substituents including oxidative cleavage of alkene and reduction, condensation and Wittig olefination of carbonyl groups.

Total Synthesis of 11-R,12-R-Dihydroxyeicosatrienoic Acid, A Metabolite of the Cytochrome P-450 Epoxygenase Pathway

The first total and enantioselective synthesis of 11-R,12-R-dihydroxy-5,8,14-eicosatrienoic acid 7 is reported.We have used the carbohydrate 2-deoxy-D-glucose as a masked 1,6-dialdehyde precursor 20 to perform the synthesis.The availability of this material will allow, among other things, the testing of the hypothesis that it can be a biochemical precursor to 12-R-HETE in vivo.

A Convenient Route for the Synthesis of 2-C-Substituted 2-Deoxyhexoses

A facile method has been developed for the synthesis of 2-C-substituted 2-deoxy-D-glucoses and 2-C-disubstituted 2-deoxy-D-arabino-hexoses using the BF3-catalyzed cyclization between 1-alkenyl ethers and 2,3-O-isopropylidene derivative of aldehydo-D-eryth

CARBON-CHAIN EXTENSION THROUGH C-1 OF 2-DEOXYALDOSE DITHIOACETAL DERIVATIVES: A ROUTE TO 1,3-DIDEOXY-2-KETOSES

The 3,4:5,6-diisopropylidene acetal (3) of 2-deoxy-D-arabino-hexose underwent abstraction of H-1 by butyllithium in oxolane at -30 deg C; iodomethane reacted readily with the resultant anion to give the 1,3-dideoxy-2-heptulose derivative 4, and C-1 benzylation could likewise be effected.Attempted deacetonation of 4 gave mixtures, although 6,7-monodeacetonation could be achieved in high yield, affording access via glycol cleavage-reduction to the 1,3-dideoxy-2-hexulose derivative.Demercaptalation of 4 gave the acetal-protected 1,3-dideoxy-2-heptulose, which underwent methanolysis to give crystalline methyl 1,3-dideoxy- α-D-arabino-heptulopyranoside.Anions of the type derived from 3 have broad, synthetic potential for access to chainextended, 2-keto sugar derivatives of interest as metabolic intermediates, and for synthesis of deoxy analogs of such nucleoside antibiotics as psicofuranine and decoyinine.