1. Hz and H. Oh-)-6h, 10 (s, 6H, CH 3 ?CvO), 2.06 (s, 6H, CH 3 ?CvO), (m, 2H, H-2 eq ) C NMR (75 MHz, CDCl 3 ) ? 170.2 (CH 3 ?CvO)CvO), 98.5 (C-1?), 98, pp.9862-9865, 1994.

1. Hz and H. , 13 C NMR (75 MHz, Acetone-d 6 ) ? 156, CvO), 156.1 (CvO), 98

1. Hz, C NMR (75 MHz, D 2 O) ? 157, 6 Hz, 1H, H-2 ax ), 1.91 (ddd, J = 12.6, 12.6, 12.6 Hz, 1H, H-2 ax )CvO), 96.0 (C-1?), 93.6 (C-1?), pp.86-87

1. Hz, 2. , and H. , (m, 17H); 13 C NMR (75 MHz, Acetoned 6 ) ? 156, EtOAc?cyclohexane 2 : 3). 1 H NMR (300 MHz 1H), 3.90 (dd, J = 9.1, 9.1 Hz, 1H), 3.80?3.39 (m, 14H), 3.38?3.25 (m, 11H), 3.25?3.05 (m, 5H), 2.44?2.28 (m, 2H, H-2 eq ) 63.1 (C?N 3 ), 60.6 (C?N 3 ), 59.4 (C?N 3 ), 59.3 (C?N 3 ), 58.6 (C?N 3 ), 51neamine pentahydrochloride 9a and 6-[[(3-azidohexylamino) carbonyl]oxy]neamine pentahydrochloride 9b By following the general procedure C, a 1 : 1 mixture of regioisomers 9a and 9b was obtaineddd, J = 9.9, 9.9 Hz, 1H), pp.3831-3835, 2003.

4. Hz, H. , and H. , Acetone-d 6 ) ? 98 HRMS (electrospray ) Calcd. for C 15 H 23 N 16 O 8 S [M ? H] ? : 587.1606, found: 587.1610. 5-(N-(3-Azidopropylamino))-6-sulfoxyneamine hexahydrochloride 13a and 6-(N-(3-azidopropylamino))-5-sulfoxyneamine hexahydrochloride 13b By following the general procedure C, a 1 : 1 mixture of regioisomers 13a and 13b was obtained (88 mg, 0.13 mmol, 66%). 1 H NMR), C NMR (75 MHz 48.5 (C?N 3 ), 48.5 (C?N 3 ), 41.3 (C-6?), 41.1 (C-6?), 36.4, 36.4, 31.5 (C-2), 31.5 (C-2) 4.85?4.60 (m, 2H, H-5?), 4.50 (dd, J = 9.7, 9.7 Hz, 1H), 4.34 (dd, J = 9.8, 9.8 Hz, 1H), 4.10?2.80 (m, 26H) C NMR (75 MHz, D 2 O) ? 95))-6-sulfoxy-1,3,2?,6?-tetraazidoneamine and 6-(N-(3- hydroxypropylamino))-5-sulfoxy-1,3,2?,6?-tetraazidoneamine By following the general procedure D, a 1 : 1 mixture of regioisomers was obtained (138 mg, 0.25 mmol, 71%). (Chromatography conditions: 40% to 50% EtOAc in cyclohexane) (R f 0, pp.55-57

1. Hz, H. Hz, 1. , H. , and H. , 13 (s, 3H, CH 3, (m, 2H), 2.46 (ddd, J = 4.58 Hz, 1H, H-2 ax ); 13 C NMR (75 MHz, pp.5-08

1. Hz, 05 (s, 3H, CH 303 (s, 3H, CH 301 (s, 3H, CH 3(3-Azidopropylamino)carbonyl]oxy]-1,3,2?,6?-tetraazido- neamine By following the general procedure B, the corresponding Odeprotected neamine derivative was obtained (83 mg, 0.15 mmol, 75%). (R f 0, C NMR (125 MHz, CDCl 3 ) ? 170.1 (CH 3 ?CvO), 169.9 (CH 3 ?CvO), 169.7 (CH 3 ? CvO), 154.7 (CvO), 98.4 (C-1?) EtOAc?cyclohexane). 1 H NMR (300 MHz, Acetone-d 6 ) ? 6.66 (s, br, 1H), 5.29 (d, J = 3.6 Hz, 1H, H-1?), 4.92 (dd, J = 9.2, 9.2 Hz, pp.60-63

1. Hz, Acetone-d 6 ) ? 156Azidopropylamino)carbonyl]oxy]-neamine pentahydrochloride 8a By following the general procedure C, 8a was obtained (97 mg, 0.16 mmol, 87%), C NMR (75 MHz 31.7 (C-2), 29.4 (C-2??); HRMS (electrospray) Calcd. for C 16 H 24 N 16 O 7 Na, pp.575-576, 1911.

. Cvo, 0; HRMS (electrospray) Calcd. for C 16 H 35 N 6 O 7 [M + H] + : 423.2562, found: 423.2565. 5. Synthesis of 8b. 6-[[(3-Azidopropylamino)carbonyl]oxy]- 1,3,2?,6?-tetraazidoneamine 8b was obtained from the 1 : 1 mixture previously prepared, by separation with reversed-phase HPLC (C 18 reversed-phase column, Interchim, 10 × 250 mm), H NMR (300 MHz, Acetone-d 6 ) ? 5.76 (t, J = 5.4 Hz, 1H), 5.62 (d, J = 3.7 Hz, 1H, H-1?), 4.81 (dd, J = 9.8, 9.8 Hz, 1H), p.18

1. Hz, Acetone-d 6 ) ? 156Azidopropylamino)carbonyl]oxy]-neamine pentahydrochloride 8b By following the general procedure C, 8b was obtained (115 mg, 0, C NMR (75 MHz 31.7 (C-2), 29.3 (C-2??). [?] +13.75 mmol, 94%). 1 H NMR (500 MHz, D 2 O) ? 5.88 (d, J = 3.9 Hz, 1H, H-1?), 4.82 (dd, J = 9.6, 9.6 Hz, 1H), pp.4-0499

1. Hz, 2. , and H. , 08 (s, 3H, CH 3, 1.90?1.60 (m, 6H, H-2??, H-2 ax ); 13 C NMR (75 MHz, CDCl 3 ) ? 170.0 (CH 3 ?CvO)0 (C-1?), 98, pp.3630-3635

1. Hz and H. , azidopropylamino)carbonyl]oxy]-1,3,2?,6?- tetraazidoneamine By following the general procedure B, the deacylated product was obtained (102 mg, 0.15 mmol, 75%), C NMR (75 MHz 58.5 (C?N 3 ), 57.9 (C?N 3 ), 50.7 (C-6)1?), 5.03 (dd, J = 9.6, 9.6 Hz, 1H, CH?OCvO?NHR), pp.2-2588

1. Hz, C. Ocvo, ?. Nhrm, 1. , and H. , 90 (dd, J = 8.9, 10.3 Hz, 1H), 3, pp.4-28

1. Hz, ddd, J = 12.1, 12.1, 12.1 Hz, 1H, H-2 ax, C NMR (75 MHz, Acetone-d 6 ) ? 155.3 (CvO), 155.2 (CvO), pp.72-59

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