Iodine(III)-Promoted azide transfer to 3-deoxyglycals

Synlett

Volumn 1995, Issue 7, 1995, Pages 767-769

  Kirschning, Andreas ^a   Domann, Silvie ^a   Dräger, Gerald ^a   Rose, Lars ^a  

^a CLAUSTHAL UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

azidoglycal; hypervalent iodine; L rhodinal; Mitsunobu reaction

Indexed keywords

EID: 0002547011     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-1995-5051     Document Type: Article

References (39)

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33. Typical experimental procedure for iodine(III)-promoted azide transfer: 1, 5- Anhydro- 3- azido- 4- O- benzoyl- 2, 3, 6- trideoxy- L-xylo-1-enitol (7a) and 4-0-Benzoyl-2, 3, 6-trideoxy-a-L-rt/-eo-hex-2-enopyranosyl azide (7c): [Caution! In our hands PhI(N3)2 turned out to be explosive, when traces of oxygen were present. Thus, the glassware was exhaustively flushed with nitrogen and was flame-dried prior to use]. To a suspension of 3 (50 mg, 0.23 mmol) and a trace of powdered molecular sieves (3A) in abs. CH2Cl2 (3 ml) was added freshly prepared iodosobenzene (100 mg, 0.46 mmol; 2 eq) and TMSN3 (0.13 ml, 0.92 mmol; 4 eq, d= 0.876) at-70 °C. The reaction mixture was slowly warmed up to rt (3 h), by which the yellow suspension turned to colorless, filtered through Celite, and finally, concentrated under reduced pressure to give a brown oil. This was purified by flash chromatography on silica gel (PE/EE 6:1) to afford 7a/7c (31 mg, 0.12 mmol, 51%) as a colorless oil: IR (cm1): v 2080; lH NMR (C6D6):8 8.08-7.00 (m, 5H, H aromat.), 6.38 (d, J12= 6.0 Hz, 1H, l-H), 5.01 (ddd, JX2= J43= J45= 1.6 Hz; 1H, 4-H), 4.38 (ddd, /2, i= 6.0 Hz, J23= 5.2 Hz, J24= 1.8 Hz, 1H, 2-H), 3.83 (dq, J54= 1.5 Hz, J5Me= 6.4 Hz, 1H, 5-H), 3.53 (dd, J32= 5.2 Hz, J34= 1.6 Hz, 1H, 3-H), 1.0 (d, JMe5= 6.4 Hz, 3H, Cff3); 13C NMR (C6D6):5 166.2, 148.5, 133.4-127.8, 94.4, 70.5, 69.0, 53.7, 16.4. Selected !H NMR data for a-7c: 5.93 (H-3), 5.37 (H-2), 4.90 (H-l), 4.86 (H-4), 3.95 (H-5), 1.11 (Me), Jl2= 3.2 Hz, Jl3= 0.8 Hz, J23=10.0 Hz, 734= 5.2 Hz, JA s= 2.4 Hz, J5 Me= 6.4 Hz.
34. When an access of PhI(N3)2 was employed exclusive formation of the bis-azido adduct 2-azido-4-0-benzoyl-2, 3, 6-trideoxy-L-(yxo-pyranosyl azide was observed.
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36. Preparation and physical data of l, 5-Anhydro-3-azido-4-0-benzyl-2, 3, 6-trideoxy-L-xy/o-l-enitol (15): To a solution of 14 (100 mg, 0.45 mmol) and LiN3 (151 mg, 2.97 mmol) in abs. DMF (3 ml) at 45 °C was added CBr4 (280 mg, 0.86 mmol) in one portion. After a while, a yellow solution resulted and PPh3 (225 mg, 0.86 mmol) was added in small portions with external cooling. After the addition was complete, the orange solution was stirred for 12 h at rt, and hydrolyzed in an ice-cold mixture of aq. NH4C1 / CH2CI2. Extraction of the aqueous phase with CH2CI2 (3x) followed by washing of the combined organic extracts with brine, drying (MgS04) and concentration in vacuo gave a brown oil (930 mg). Purification by flash chromatography on silica gel (PE/EE 20:1) afforded 15 (17 mg, 0.07 mmol, 15%) as a colorless oil: IR (cm1): v 2080; !H NMR (C6D6):5 7.2-7.0 (m, 5H, H aromat), 6.36 (d, Jl2= 6.4 Hz, 1H, l-H), 4.44 (ddd, J1X= 6.4 Hz, J13= 5.2 Hz, J2, 4= 1-4 Hz, 1H, 2-H), 4.23, 4.04 (2d, JAB= 12.0 Hz, 2H, CH2Ph), 3.78 (dq, J5A= 2.0 Hz, J5Me= 6.4 Hz, 1H, 5-7?), 3.54 (dd, J32= 5.2 Hz, J3 4= 2.0 Hz, 1H, 3-H), 3.09 (ddd, J42= 1.4 Hz, Ji3= 2.0 Hz, J45= 2.0 Hz, 1H, A-H), 1.11 (d, JMe5= 6.4 Hz, 3H, CH3); 13C NMR (C6D6):8 148.2, 133.2, 128.0-127.8, 94.3, 76.5, 72.3, 70.2, 53.4, 15.9.
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