198775-13-2

Upstream product

• 136764-17-5 3'-Phenyl-2',3'-methanopropyl 2-O-<<(trifluoromethyl)sulfonyl>oxy>-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 37699-02-8 (3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde 
• 136764-32-4 (2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((1S,2S)-2-phenyl-cyclopropylmethoxy)-tetrahydro-pyran-3-ol 

Downstream Products

• 77890-04-1 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-ribo-hexitol 
• 75499-83-1 2,5-anhydro-4,5-di-O-benzoyl-D-glucitol 
• 75499-82-0 2,5-anhydro-4,5-di-O-benzoyl-1,3-O-isopropylidene-D-glucitol 
• 177171-88-9 ((2R,4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-methanol 
• 198775-17-6 2,5-anhydro-4,6-di-O-benzyl-D-glucitol 
• 198775-25-6 ((2R,5S)-5-Trityloxymethyl-2,5-dihydro-furan-2-yl)-methanol 
• 198775-19-8 2,5-anhydro-4,6-di-O-benzoyl-1-O-t-butyldimethylsilyl-D-glucitol 
• 198775-23-4 2,5-anhydro-1-O-t-butyldimethylsilyl-6-O-triphenylmethyl-D-erythro-hex-3,4-enitol 
• 198775-21-2 2,5-anhydro-1-O-t-butyldimethylsilyl-6-O-triphenylmethyl-D-glucitol 
• 198775-36-9 2,5-anhydro-4,6-di-O-benzoyl-1-(N-3-benzoylthymin-1-yl)-3-deoxy-D-ribo-hexitol 
• 198775-27-8 3-Benzoyl-5-methyl-1-((2R,5S)-5-trityloxymethyl-2,5-dihydro-furan-2-ylmethyl)-1H-pyrimidine-2,4-dione 
• 109065-82-9 2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-1-(phenylselenyl)-D-mannitol 
• 109121-40-6 2,5-anhydro-3,4,6-tri-O-benzyl-1-deoxy-1-(phenylselenyl)-D-glucitol 
• 102093-88-9 (2R,3R,4S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-bromomethyl-tetrahydro-furan 

Relevant academic research and scientific papers

Asymmetric Cyclopropanation of Allylic Ethers: Cleavage and Regeneration of the Chiral Auxiliary

The ring contraction reaction of 2-O-oxy>-β-D-glucopyranosides and their corresponding α-anomers is reported.The rearrangement was shown to occur under extremely mild basic conditions to allow isolation of acid-sensitive optica

D-arbinose-based synthesis of homo-C-d4T and homo-C-thymidine

2,3,5-Tri-O-benzyl-D-arabinofuranosyl halides (chloride, bromide) were reacted with AllMgBr, MeMgBr, and VinMgBr to furnish anomeric mixtures of the C-glycosyl products. The factors that influenced the β/α ratio are discussed. The α,β-C-vinyl derivative was transformed into 1-deoxy-1-C-hydroxymethyl-β and α-D-arabinofuranoses (2,5-anhydro-D-glucitol and -mannitol, respectively), separable after isopropylidenation step. 2,5-Anhydro-1,3-O-isopropylidene-D-glucitol was converted into 2,5-anhydro-6-O-triphenylmethyl-D-erythro-hex-3,4-enitol and 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-ribo-hexitol, which were coupled with N-3-benzoylthymine under the Mitsunobu conditions to furnish two analogs of nucleosides with a -CH2- insert between sugar moieties and thymine. (Chemical Equation Presented).

Synthesis of homo-C-D4T and homo-C-thymidine

β-C-Vinyl glycoside of D-arabinofuranose was converted to the β-C- hydroxymethyl glycoside 12 which was condensed with N-3-benzoyl thymine under Mitsunobu conditions to furnish homo-C-analog 14 of the 2',3'-dideoxy-2',3'- didehydrothymidine (D4T). Synthesis of the homo-C-thymidine 18 was accomplished by the same procedure from compound 15.