6160-56-1

Upstream product

• 67-56-1 methanol 
• 22900-10-3 2-deoxy-D-ribose 
• 496-62-8 D-xylal 

Downstream Products

• 197715-54-1 (1R,4S,6R)-4-methoxy-7-acetyl-3-oxa-7-azabicyclo[4.1.0]heptane 
• 197715-58-5 (1R,4S,6R)-4-Methoxy-3-oxa-7-aza-bicyclo[4.1.0]heptane-7-carboxylic acid benzyl ester 
• 197715-60-9 ((3S,4S,6S)-4,6-Dimethoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester 
• 55700-61-3 methyl 2-deoxy-α-D-threo-pentopyranoside 
• 1333965-76-6 BPh(Me-α-D-ery-dPenp3,4H-2) 

Relevant academic research and scientific papers

An efficient stereoselective synthesis of the amino sugar component (E ring) of calicheamicin γ1(I)

A simple, efficient, stereoselective synthesis of the methyl 2,4-dideoxy-4-(ethylamino)-3-O-methyl-β-L-threo-pentopyranoside 2, corresponding to the E monosaccharide unit (E ring) of calicheamicin 1, is described. The synthetic procedure utilizes the methyl 2-deoxy-β-D-ribopyranoside 3 as the enantiopure starting material and the acid methanolysis of the intermediate activated aziridine 12 to give the desired amino sugar 2 in 6 steps and in satisfactorily high overall yield (60%). No separation stage is necessary at any point of the synthetic process.

4'-Thionucleosides via in situ pyranose-furanose rearrangements: A short synthesis of the antiherpes agent 2'-deoxy-5-ethyl-4'-thiouridine via direct coupling of a silylated pyrimidine base with a 4-thiopyranose sugar

Methyl 2-deoxy-3,4-O-thiocarbonyl-β-D-ribopyranoside was converted into the thione carbonate by reaction with thiophosgene. Bromide ion-catalyzed O-S rearrangement produced methyl 2-deoxy-3-O,4-S-carbonyl-4-thio-β-D- ribopyranoside (3a) and the 3-O,4-S isomer 3b. The carbonates were cleaved with ammonia and the 3-O,4-S pyranoside sugar coupled with bis(trimethylsilyl)-5-ethyluracil using trimethylsilyl triflate to provide the antiherpes agenet 2'-deoxy-5-ethyl-4'-thiouridine 9. The reaction proceeded via in situ pyranoside rearrangement of the sugar and subsequent coupling. The pyranoside sugar could also be converted to the furanoside form with Dowes H+ acid resin and coupled in conventional fashion to give the nucleoside. Coupling of methyl 4-O-carbamoyl-2-deoxy-3-thio-β-D- ribopyranoside (4b) with the bis(trimethylsilyl)-5-ethyluracil gave 1-[2-[2- (hydroxymethyl)thiiran-1-yl]-1-methoxyethyl]-5-ethyluracil.

METHYL ETHERS OF METHYL 2-DEOXY-α- AND β-D-threo-PENTOPYRANOSIDE

Methyl 2-deoxy-α- and β-D-threo-pentopyranosides (Ia, IIa) were prepared.Various conditions for partial methylation of the β-anomer IIa were tried out, leading to methyl 2-deoxy-3-O-methyl-β-D-threo-pentopyranoside (IIc), methyl 2-deoxy-4-O-methyl-β-D-threo-pentopyranoside (IId) and methyl 2-deoxy-3,4-di-O-methyl-β-D-threo-pentopyranoside (IIe).The structures of the products were determined by means of 1H NMR.