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1 Eur. J. Org. Chem WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim, 2004 ISSN X SUPPORTING INFORMATION Title: δ-galactonolactone:synthesis, Isolation, and Comparative Structure and Stability Analysis of an Elusive Sugar Derivative Author(s): Matthias Bierenstiel, Marcel Schlaf* Ref. No.: O03761
2 Table S1: Effectiveness of Various Hydrogen Acceptors for the Catalytic Dehydrogenation of D-Glucose in DMF by 7. a Acceptor Amount Reaction Time [h] γ/δ-ratio Lactone b Cyclohexanone 5 ml = 33 eq. 2 3 %: 97 % Acetone 5 ml = 46 eq %: 93 % 3-pentanone 5 ml = 32 eq %: 88% Acetophenone 5 ml = 29 eq %: 90% a Reaction conditions: D-glucose (265 mg = 1.47 mmol) in 7 ml dry DMF, 45 ºC, 1.25 mol % 7 (29 mg = mmol ). b By 1 H NMR of isolated materials.
3 Table S2: 1 H NMR data of γ-lactones 4b, 5b and 6b in DMSO-d 6 at 400 MHz. Hydroxyl Shifts OH-2 OH-3 OH-5 OH-6 Gamma gluconolactone Gamma galactonolactone Gamma mannonolactone 6.20 (1H, d, J = 5.4 Hz) 5.58 (1H, d, J = 4.5 Hz) 4.93 (1H, d, J = 5.9 Hz) 4.63 (1H, t, J = 5.7 Hz) 6.02 (1H, d, J = 6.6 Hz) 5.74 (1H, d, J = 5.6 Hz) 4.99 (1H, d, J = 6.2 Hz) 4.74 (1H, t, J = 5.6 Hz) 5.76 (1H, d, J = 7.6 Hz) 5.29 (1H, d, J = 4.4 Hz) 4.82 (1H, d, J = 6.0 Hz) 4.58 (1H, t, J = 5.6 Hz) C-H Shifts H-2 H-3 H-4 H-5 H-6 H-6 Gamma 4.04 (1H, dd, J = 4.12 (1H, dd, J = 4.40 (1H, dd, J = 3.76 (1H, m) 3.55 (1H, m) 3.45 (1H, m) gluconolactone 3.9 Hz, 5.4 Hz) 3.9 Hz, 4.6 Hz) 2.1 Hz, 4.7 Hz) Gamma 3.59 (1H, ddd, J = 4.22 (1H, dd, J = galactonolactone 4.12 (1H, m) 4.07 (1H, m) 1.6 Hz, 4.7 Hz, (1H, m) 3.38 (1H, m) 1.6 Hz, 6.6 Hz) Hz) Gamma 4.22 (1H, ddd, J = 3.72 (1H, ddd, J = 3.55 (1H, ddd, J = 4.45 (1H, dd, J = 4.13 (1H, dd J = mannonolactone 4.2 Hz, 4.4 Hz, Hz, 2.8 Hz, Hz, 5.6 Hz, 3.50 (1H, m) 4.2 Hz, 7.6 Hz) 2.4 Hz, 6.8 Hz) Hz) Hz) 11.6 Hz)
4 Table S3: 13 C NMR data of γ-lactones 4b, 5b and 6b in DMSO-d 6 at 400 MHz. Gamma gluconolactone Gamma galactonolactone Gamma mannonolactone C-1 C-2 C-3 C-4 C-5 C
5 delta-gluconolactone (1H, 400 MHz, DMSO-d6) ppm
6 delta-gluconolactone (jmod, 100 MHz, DMSO-d6) CH2 and quaternary up, CH3 and CH down ppm
7 delta-gluconolactone (COSY, 400 MHz, DMSO-d6) ppm ppm
8 delta-gluconolactone (HSQC, 400 MHz/100 MHz, DMSO-d6) ppm ppm
9 gamma-gluconolactone (with small amount of delta-gluconolactone) (1H, 400 MHz, DMSO-d6) ppm
10 gamma-gluconolactone (with small amount of delta-gluconolactone) (jmod, 100 MHz, DMSO-d6) CH2 and quaternary up, CH3 and CH down ppm
11 gamma-gluconolactone (with small amount of delta-gluconolactone) (COSY, 400 MHz, DMSO-d6) ppm ppm
12 gamma-gluconolactone (with small amount of delta-gluconolactone) (HSQC, 400 MHz/100 MHz, DMSO-d6) ppm ppm
13 delta-mannonolactone (with small amount of gamma-mannonolactone) (1H, 400 MHz, DMSO-d6) ppm
14 delta-mannonolactone (with small amount of gamma-mannonolactone) (jmod, 100 MHz, DMSO-d6) CH2 and quaternary up, CH3 and CH down ppm
15 delta-mannonolactone (with small amount of gamma-mannonolactone) (COSY, 400 MHz, DMSO-d6) ppm ppm
16 delta-mannonolactone (with small amount of gamma-mannonolactone) (HSQC, 400 MHz/100 MHz, DMSO-d6) ppm ppm
17 gamma-mannonolactone (with small content of delta-mannonolactone and water) (1H, 400 MHz, DMSO-d6) ppm
18 gamma-mannonolactone (with small content of delta-mannonolactone and water) (jmod, 100 MHz, DMSO-d6) CH2 and quaternary up, CH3 and CH down ppm
19 gamma-mannonolactone (with small content of delta-mannonolactone and water) (COSY, 400 MHz, DMSO-d6) ppm ppm
20 gamma-mannonolactone (with small content of delta-mannonolactone and water) (HSQC, 400 MHz/100 MHz, DMSO-d6) ppm ppm
21 delta-galactonolactone (with small amount of gamma-galactonolactone) (1H, 400 MHz, DMSO-d6) ppm
22 delta-galactonolactone (with small amount of gamma-galactonolactone) (jmod, 100 MHz, DMSO-d6) CH2 and quaternary up, CH3 and CH down ppm
23 delta-galactonolactone (with small content of gamma-galactonolactone) (COSY, 400 MHz, DMSO-d6) ppm ppm
24 delta-galactonolactone (with small amount of gamma-galactonolactone) (HSQC, 400 MHz/100 MHz, DMSO-d6) ppm ppm
25 gamma-galactonolactone (1H, 400 MHz, DMSO-d6) ppm
26 gamma-galactonolactone (jmod, 100 MHz, DMSO-d6) CH2 and quaternary up, CH3 and CH down ppm
27 gamma-galactonolactone (COSY, 400 MHz, DMSO-d6) ppm ppm
28 gamma-galactonolactone (HSQC, 100 MHz, DMSO-d6) ppm ppm
29 Atomic coorddinates for all lactones from from mpw1pw91 DFT calculations with the 6-31(d,p) (optimized) and the Onsager reaction field model in DMSO: (The data represent direct Gaussian 03 input files rewritten from the final optimized geometries using GaussView 03).
30 δ-d-gluconolactone %mem=6mw %nproc=1 # freq rmpw1pw91/6-31g(d,p) geom=(connectivity,allcheck) guess=tcheck delta gluco_solvent1 0 1 H C 1 B1 C 2 B2 1 A1 C 2 B3 1 A2 3 D1 C 3 B4 2 A3 1 D2 O 2 B5 1 A4 4 D3 C 3 B6 2 A5 1 D4 H 3 B7 2 A6 1 D5 H 4 B8 2 A7 1 D6 H 5 B9 3 A8 2 D7 O 7 B10 3 A9 2 D8 H 7 B11 3 A10 2 D9 O 2 B12 1 A11 4 D10
31 O 3 B13 2 A12 1 D11 C 4 B14 2 A13 1 D12 O 5 B15 3 A14 2 D13 H 11 B16 7 A15 3 D14 H 14 B17 3 A16 2 D15 H 16 B18 5 A17 3 D16 H 15 B19 4 A18 2 D17 O 15 B20 4 A19 2 D18 H 15 B21 4 A20 2 D19 B B B B B B B B B B B
32 B B B B B B B B B B A A A A A A A A A A A
33 A A A A A A A A A D D D D D D D D D D D D
34 D D D D D D D
35
36 γ-d-gluconolactone %mem=6mw %nproc=1 %chk=gamma_gluco_solvent.chk # freq rmpw1pw91/6-31g(d,p) geom=(connectivity,allcheck) guess=tcheck gamma_gluco_solvent1 0 1 H O 1 B1 C 2 B2 1 A1 C 3 B3 2 A2 1 D1 C 4 B4 3 A3 2 D2 C 2 B5 1 A4 5 D3 C 6 B6 2 A5 1 D4 O 5 B7 4 A6 3 D5 H 5 B8 4 A7 3 D6 O 4 B9 3 A8 2 D7 H 4 B10 3 A9 2 D8 O 3 B11 2 A10 1 D9
37 H 10 B12 4 A11 3 D10 H 8 B13 5 A12 4 D11 O 7 B14 6 A13 2 D12 C 7 B15 6 A14 2 D13 H 7 B16 6 A15 2 D14 H 16 B17 7 A16 6 D15 H 16 B18 7 A17 6 D16 O 16 B19 7 A18 6 D17 H 20 B20 16 A19 7 D18 H 15 B21 7 A20 6 D19 B B B B B B B B B B
38 B B B B B B B B B B B A A A A A A A A A A
39 A A A A A A A A A A D D D D D D D D D D D
40 D D D D D D D D
41
42 δ-d-mannonolactone %chk=c:/g03w/output/mannoboat_dmso_onsager_mp.chk %mem=6mw %nproc=1 # freq rmpw1pw91/6-31g(d,p) scrf=(solvent=water,check) guess=read geom=(connectivity,allcheck) genchk 0 1 H C 1 B1 C 1 B2 2 A1 C 2 B3 1 A2 3 D1 C 4 B4 2 A3 1 D2 O 2 B5 1 A4 3 D3 C 2 B6 1 A5 3 D4 H 3 B7 1 A6 7 D5 H 4 B8 2 A7 1 D6 H 5 B9 4 A8 2 D7 O 5 B10 4 A9 2 D8 O 7 B11 2 A10 1 D9
43 O 2 B12 1 A11 7 D10 O 3 B13 1 A12 7 D11 C 4 B14 2 A13 1 D12 O 15 B15 4 A14 2 D13 H 15 B16 4 A15 2 D14 H 15 B17 4 A16 2 D15 H 12 B18 7 A17 2 D16 H 14 B19 3 A18 1 D17 H 11 B20 5 A19 4 D18 H 16 B21 15 A20 4 D19 B B B B B B B B B B
44 B B B B B B B B B B B A A A A A A A A A A
45 A A A A A A A A A A D D D D D D D D D D D
46 D D D D D D D D
47
48 γ-d-mannonolactone %mem=6mw %nproc=1 # freq rmpw1pw91/6-31g(d,p) geom=(connectivity,allcheck) guess=tcheck gamma_manno_solvent1 0 1 H O 1 B1 C 2 B2 1 A1 C 3 B3 2 A2 1 D1 C 4 B4 3 A3 2 D2 C 2 B5 1 A4 5 D3 C 6 B6 2 A5 1 D4 O 5 B7 4 A6 3 D5 H 5 B8 4 A7 3 D6 H 7 B9 6 A8 2 D7 O 4 B10 3 A9 2 D8 O 3 B11 2 A10 1 D9 H 4 B12 3 A11 2 D10
49 H 8 B13 5 A12 4 D11 O 7 B14 6 A13 2 D12 C 7 B15 6 A14 2 D13 H 7 B16 6 A15 2 D14 H 16 B17 7 A16 6 D15 H 16 B18 7 A17 6 D16 O 16 B19 7 A18 6 D17 H 20 B20 16 A19 7 D18 H 11 B21 4 A20 3 D19 B B B B B B B B B B B
50 B B B B B B B B B B A A A A A A A A A A A
51 A A A A A A A A A D D D D D D D D D D D D
52 D D D D D D D
53
54 δ-d-galactonolactone %mem=6mw %nproc=1 # freq rmpw1pw91/6-31g(d,p) geom=connectivity guess=tcheck delta_galac_solvent1 0 1 H C 1 B1 C 1 B2 2 A1 C 2 B3 1 A2 3 D1 C 3 B4 1 A3 4 D2 O 2 B5 1 A4 5 D3 C 2 B6 1 A5 5 D4 H 3 B7 1 A6 5 D5 H 4 B8 2 A7 1 D6 O 5 B9 3 A8 1 D7 O 4 B10 2 A9 1 D8 H 7 B11 2 A10 1 D9 O 2 B12 1 A11 10 D10
55 O 3 B13 1 A12 10 D11 C 11 B14 4 A13 2 D12 H 7 B15 2 A14 1 D13 O 7 B16 2 A15 1 D14 H 14 B17 3 A16 1 D15 H 5 B18 3 A17 1 D16 H 15 B19 11 A18 4 D17 H 15 B20 11 A19 4 D18 H 11 B21 4 A20 2 D19 B B B B B B B B B B B
56 B B B B B B B B B B A A A A A A A A A A A
57 A A A A A A A A A D D D D D D D D D D D D
58 D D D D D D D
59
60 γ-d-galactonolactone %mem=6mw %nproc=1 # freq rmpw1pw91/6-31g(d,p) geom=(connectivity,allcheck) guess=tcheck gamma_galac_solvent1 0 1 C O 1 B1 C 2 B2 1 A1 C 3 B3 2 A2 1 D1 C 4 B4 3 A3 2 D2 C 2 B5 1 A4 5 D3 H 5 B6 4 A5 3 D4 O 5 B7 4 A6 3 D5 H 5 B8 4 A7 3 D6 H 6 B9 2 A8 1 D7 H 4 B10 3 A9 2 D8 O 3 B11 2 A10 1 D9 O 4 B12 3 A11 2 D10
61 H 13 B13 4 A12 3 D11 H 1 B14 6 A13 2 D12 O 1 B15 6 A14 2 D13 C 1 B16 16 A15 6 D14 H 17 B17 1 A16 16 D15 H 17 B18 1 A17 16 D16 O 17 B19 1 A18 16 D17 H 20 B20 17 A19 1 D18 H 16 B21 1 A20 6 D19 B B B B B B B B B B B
62 B B B B B B B B B B A A A A A A A A A A A
63 A A A A A A A A A D D D D D D D D D D D D
64 D D D D D D D
65
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