120567-49-9

Upstream product

• 186581-53-3 diazomethane 
• 911380-51-3 methyl 2,3,4-tri-O-benzyl-β-L-idopyranosiduronate 
• 158535-94-5 Methyl (2R,3S,4S,5R)-3,4,5-tris(benzyloxy)-2-(methoxymethoxy)-6-oxohexanoate 
• 158535-92-3 Methyl (2R,3S,4R,5S)-3,4,5-tris(benzyloxy)-6-<(tert-butyldimethylsilyl)oxy>-2-(methoxymethoxy)hexanoate 
• 158535-93-4 Methyl (2R,3S,4R,5S)-3,4,5-tris(benzyloxy)-6-hydroxy-2-(methoxymethoxy)hexanoate 
• 641635-63-4 ((3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-methanol 

Downstream Products

• 528584-66-9 dimethyl β-L-idopyranosiduronate 

Relevant academic research and scientific papers

Divergent synthesis of L-sugars and L-iminosugars from D-sugars

An efficient divergent synthesis of L-sugars and L-iminosugars from D-sugars is described. The important intermediate. δ-hydroxyalkoxamate. prepared from D-glucono-/galactono-1,5-lactone, was cyclized under Mitsunobu conditions to give the O-cyclized oxim

Synthesis of L-pyranosides from 5-enopyranosides by diastereoselective hydroboration/oxidation

Improved synthesis of L-pyranosides utilizing diastereoselective hydroboration/oxidation of 5-enopyranosides was investigated. A unique phenomenon in the diastereoselectivity of the hydroboration was incidentally found. The method was successfully applied to the synthesis of L-iduronic acid.

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.