102436-29-3

Upstream product

• 112995-85-4 (R)-4-((1S,2S)-1,2-bis(benzyloxy)but-3-enyl)-2,2-dimethyl-1,3-dioxolane 
• 222408-69-7 3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-D-altritol 
• 100-39-0 benzyl bromide 
• 155049-25-5 (2R,3R)-2-O-tert-butyldimethylsilyl-3,4-O-cyclohexylidene-2,3,4-trihydroxybutanal 
• 1387444-51-0 (2R,3S,4S)-1,2-O-cyclohexylidene-3-O-(tert-butyldimethylsilyl)hex-5-ene-1,2,3,4-tetrol 
• 1387444-53-2 (2R,3S,4S)-1,2-O-cyclohexylidene-3,4-O-dibenzylhex-5-ene-1,2,3,4-tetrol 
• 102436-28-2 meso-di-O-benzyl-divinylglycol 
• 160849-24-1 2,3-di-O-benzyl-4,5-O-isopropylidene-D-ribose diethyl-dithioacetal 
• 25572-71-8 4,5-O-isopropylidene-D-ribose diethyl dithioacetal 
• 103795-16-0 2,3-di-O-benzyl-4,5-O-isopropylidene-D-ribose 
• 7152-47-8 D-ribose diethyl dithioacetal 
• 222408-68-6 3,4-di-O-benzyl-1-deoxy-1-dimethylphenylsilyl-5,6-O-isopropylidene-D-altritol 

Downstream Products

• 1175536-39-6 (R)-2-((1S,2S)-1,2-bis(benzyloxy)but-3-enyl)oxirane 
• 1387444-55-4 (4R,5R,6S)-5,6-dibenzyloxyoct-7-en-4-yl (2R)-2-benzyloxyhex-5-enoate 
• 1402571-64-5 C₂₇H₃₀O₆S 
• 112995-86-5 2,3-di-O-benzyl-L-erythro-pent-4-enose 
• 112995-87-6 6,7-di-O-benzyl-1,3,4,5,8,9-hexadeoxy-L-erythro-non-4,8-dieno-2-ulose 

Relevant academic research and scientific papers

Formal and total syntheses of herbarumin i and II, respectively from (R)-2,3-cyclohexylideneglyceraldehyde

Vinyl Grignard addition to 2, obtained via a nitroaldol reaction of (R)-2,3-cyclohexylideneglyceraldehyde 1, afforded 3 with absolute stereoselectivity. This was transformed into 7, a known intermediate for the formal synthesis of herbarumin I A. Condensation of 7 with 10, another intermediate obtained from 1 afforded 11. The RCM reaction of 11 in the presence of Grubbs second generation catalyst Ru II and global debenzylation of the product in the presence of TiCl4 furnished B. The efficacy of the entire route was due to its operational simplicity, the easy accessibility of 1, all of the reactions being inexpensive and the high stereoselectivity of the asymmetric C-C bond forming reactions involved, as well as E-selectivity of the RCM reaction.

A new synthesis of the phytotoxic 10-membered lactone herbarumin I

Herbarumin I a phytotoxic 10-membered lactone has been synthesized from d-(-)-isoascorbic acid in 12 steps with an overall yield of 16.8%. The methodology involved in generating the stereogenic center at C-8 is a Sharpless asymmetric epoxidation, as well 1,2-asymmetric induction followed by macrolactonization via RCM.

Preparation of 2,5-anhydrohexitols (part I). Silicon-directed stereocontrolled cyclization

Stereoselective chain-extension of carbohydrate aldehydes with the hydroxymethylating reagent (dimethylphenylsilyl)methylmagnesium chloride (1) followed by acid-mediated cyclization gives access to 2,5-anhydro-hexitols. The stereoselectivity of the ring closure depends on the nature of the acid, i.e., treatment with excess BF3·Et2O or catalytic H2SO4 leads to tetrahydrofurans with 2,3-cis or 2,3-trans configuration, respectively. Concomitant elimination is effectively suppressed in case of cyclisation of the more sterically hindered isopropyl substituted silanes.

Chiral building units from carbohydrates-XIII. Identification of the absolute configuration of endo-brevicomin from dendroctonus frontalis and synthesis of both enantiomers from d-ribose

The synthesis of both enantiomers of endo-7-ethyl-5-methyl-6,8-dioxabicyclo[3.2.l]octana (endo-brevicomin, 12 and 12a) starting froni D-ri-bose is described. Key interinediate is the open chain derivative 7, a chiral building unit easily available from ca

De novo Synthesis of Carbohydrates and Related Natural Products, 23. - Synthesis of 2-Deoxy-DL-ribo-hexose and 6-Deoxy-DL-talose from meso-Divinylglycols

cis-Dihydroxylation of meso-di-O-benzyl-divinylglycol 4 and of the corresponding dipropenylglycol 12 with osmium tetraoxide/N-methylmorpholine N-oxide affords diastereoselectively the DL-ribo-5-hexenetetrol (+/-)-5a and the DL-altro-6-octenetetrol (+/-)-1