131379-07-2

Upstream product

• 77312-71-1 diethyl (2R,3R)-2,3-bis(benzyloxy)butane-1,4-dioate 
• 113427-43-3 1,4-di-O-benzyl-L-threitol 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 162631-06-3 (2S,3R,4S,5R)-1-<(tert-butyldimethylsilyl)oxy>-2,3-bis(benzyloxy)-5-<(2,3:4,6-di-O-isopropylidene-α-D-mannopyranosyl)oxy>hept-6-en-4-ol 
• 158646-95-8 (2S,3R,4S,5S,6E)-2,3-Bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-5-(methoxymethoxy)-6-octen-4-ol 
• 174061-08-6 (6E,2S,3R,4R,5R)-2,3-bis(benzyloxy)-1-<(tert-butyldimethylsilyl)oxy>-5-(methoxymethoxy)-6-octen-4-ol 
• 653591-62-9 (4R,5S)-3-[(1R,2S,3S,4S)-3,4-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-1-trimethylsilanylethynyl-pentyl]-4,5-diphenyl-oxazolidin-2-one 
• 131379-09-4 4,5-Di-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-O-(methoxymethyl)-L-galactitol 
• 131379-12-9 1,3,4,5-Tetra-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-O-(methoxymethyl)-L-galactitol 
• 1420298-20-9 (4S,5S,E)-ethyl 4,5-bis(benzyloxy)-6-(tert-butyldimethylsilyloxy)hex-2-enoate 
• 1420298-18-5 (2S,3S,4S)-1-(tert-butyloxycarbonyl)-3,4-bis(benzyloxy)-2-ethenylpyrrolidine 
• 1420298-19-6 (4S,5S,E)-4,5-bis(benzyloxy)-6-(tertbutoxycarbonylamino)-1-pivaloylhex-2-ene 
• 1420298-25-4 (4S,5S,E)-4,5-bis(benzyloxy)-6-(tertbutoxycarbonylamino)pivaloyloxyhex-2-ene 
• 1420298-24-3 (4S,5S,E)-6-azido-4,5-bis(benzyloxy)-1-pivaloyloxyhex-2-ene 
• 1420298-23-2 (4S,5S,E)-4,5-bis(benzyloxy)-6-hydroxy-1-pivaloyloxyhex-2-ene 
• 1420298-22-1 (4S,5S,E)-4,5-bis(benzyloxy)-6-(tertbutyldimethylsilyloxy)-1-pivaloylhex-2-ene 

Relevant academic research and scientific papers

Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H

1,6-Diynes with a t-butylcarbonate group in the propargylic position undergo gold(I)-catalyzed domino-cyclization which affords α-hydroxycyclohexenones. The described sequence can be applied on functionalized, highly oxygenated substrates, as examplified

Synthesis of Protected Carbohydrate Derivatives through Homologation of Threose and Erythrose Derivatives with Chiral γ-Alkoxy Allylic Stannanes

Additions of the γ-alkoxy allylic stannanes (S)-1 and (R)-1 and the racemate (RS)-1 to the threose and erythrose aldehyde derivatives 6 and 15 in the presence of BF3*OEt2 or MgBr2*OEt2 were examined in order to establish stereochemical preferences.It was found that (S)-1 and aldehyde 6 afforded the syn,anti,syn adduct 7 in the BF3-promoted reaction, while (R)-1 and 6 gave the syn,syn,syn adduct 8 under MgBr2 conditions.Likewise, (S)-1 and aldehyde 15 yielded the syn,anti,anti adduct 16 with BF3, whereas (R)-1 and 15 led to the syn,syn,anti adduct 17 with MgBr2.The MgBr2-promoted reactions showed sufficient rate differences between the matched and mismatched stannanes to allow the use of racemic stannane (RS)-1 in just over 2-fold excess, whereupon the matched adducts 8 and 17 were favored by greater than 9:1 over the mismatched adducts.The major adducts 7, 8, 16, and 17 were converted to the hexose derivatives 21, 30/31, 34, and 39 by ozonolysis, selective deprotection, and refunctionalization.Adducts 16 and 17 were dihydroxylated with OsO4-NMO to the deoxyoctose precursors 40/41 and 42/43.

Diastereoselective Additions of Enantioenriched (γ-Alkoxyallyl)stannanes to α-Alkoxy Aldehydes: A Synthetic Route to Carbohydrates

BF3*OEt2-promoted additions of the (S)-(γ-alkoxyallyl)stannane 3-(S) to the (R)-α-alkoxy aldehydes 13 and 18 affords the syn adducts 14 and 19 with greater than 90:10 diastereoselectivity.With MgBr2 as the catalyst addition to the (S)-α-alkoxy aldehyde 4 is most selective (97:3) with the (S)-(γ-alkoxyallyl)stannane 3-(S) whereas BF3-promoted addition to 4 is most selective (92:8) with the R enantiomer 3-(R).