ࡱ>  G Nbjbjَ "( ]00000$T 0 l^  $5 ) ~ u JlJJJ 00 JJ  ` 000j Supporting Information Tetra-O-benzyl-a-D-galactopyranosyl-1-(2R/S)-glycerol  EMBED ChemDraw.Document.5.0  HiRes: Calcd. M+Na 637.2777, found 637.2778 Superimposition of R and S epimers: 7.4-7.2 (m, 20 H, arom.), 4.91 (d, 1 H, 2J 11.5 Hz, Bn), 4.84-4.77 (m, 3 H, Bn, H-1), 4.72 (d, 1 H, 2J 11.8 Hz, Bn), 4.65 (4 lines, 1 H, 2J 11.9 Hz, Bn), 4.55 (d, 1 H, 2J 11.5 Hz, Bn), 4.46 (4 lines, 1 H, 2J 11.6 Hz, Bn), 4.38 (d, 1 H, 2J 11.8 Hz, Bn), 4.05-4.01 (m, 1 H, H-2), 4.98 (dd, 1 H, J5,6a 6.3 Hz, J5,6b 12.7 Hz, H-5), 3.92-3.87 (m, 2 H, H-3, H-4), 3.86-3.40 (m, 7 H, H-6a, H-6b, glycerol), 3.3-3.4 (1 H, OH), 2.34-2.30 (0.6 H, part. OH), 2.21-2.18 (0.4 H, part. OH). Tetra-O-benzyl-a-D-galactopyranosyl-2-ethanal  EMBED ChemDraw.Document.5.0  HiRes: Calcd. M+Na 605.2515, found 605.2507 9.70 (s, 1 H, CH=O), 7.38-7.24 (m, 20 H, arom.), 4.92 (d, 1 H, 2J 11.5 Hz, Bn), 4.86-4.82 (m, 3 H, H-1, Bn), 4.73 (d, 1 H, 2J 9.2 Hz, Bn), 4.71 (d, 1 H, 2J 9.2 Hz, Bn), 4.55 (d, 1 H, 2J 11.4 Hz, Bn), 4.44 (d, 1 H, 2J 11.9 Hz, Bn), 4.37 (d, 1 H, 2J 11.9 Hz, Bn), 4.16 (d, 1 H, 2J 17.9 Hz, CH2), 4.10 (d, 1 H, CH2), 4.08 (dd, 1 H, J1,2 3.7 Hz, J2,3 10.1 Hz, H-2), 3.99-3.94 (m, 3 H, H-3, H-4, H-5), 3.47 (d, 2 H, J5,6 6.4 Hz, H-6a, H-6b). 2,3,4,6-Tetra-O-benzyl-1-O-formyl-a-D-galactopyranose  EMBED ChemDraw.Document.5.0  HiRes: Calcd. M+Na 591.2358, found 591.2352 8.12 (s, 1 H, CH=O), 7.38-7.24 (m, 20 H, arom.), 6.38 (d, 1 H, J1,2 3.7 Hz, H-1), 4.93 (d, 1 H, 2J 11.5 Hz, Bn), 4.80 (d, 1 H, 2J 11.8 Hz, Bn), 4.74-4.70 (m, 2 H, Bn), 4.57 (d, 1 H, 2J 11.3 Hz, Bn), 4.44 (d, 1 H, 2J 11.7 Hz, Bn), 4.38 (d, 1 H, 2J 11.7 Hz, Bn), 4.17 (dd, 1 H, , J2,3 9.7 Hz, H-2), 4.04-4.00 (m, 2 H, H-4, H-5), 3.88 (dd, 1 H, J3,4 2.7 Hz, H-3), 3.54 (dd, 1 H, J6a,6b 9.3 Hz, H-6a), 3.50 (dd, 1 H, H-6b). Tetra-O-benzyl-D-1,5-galactonolactone  EMBED ChemDraw.Document.5.0  HiRes: Calcd. M+Na 561.2253, found 561.2254 7.4-7.2 (m, 20 H, arom.), 5.16 (d, 1 H, 2J 11.0 Hz, Bn), 4.91 (d, 1 H, 2J 11.3 Hz, Bn), 4.76 (d, 1 H, 2J 11.3 Hz, Bn), 4.74 (d, 1 H, 2J 12.7 Hz, Bn), 4.67 (d, 1 H, 2J 11.9 Hz, Bn), 4.59 (d, 1 H, 2J 11.3 Hz, Bn), 4.50-4.42 (m, 3 H, Bn, H-2), 4.32 (ddd, 1 H, J4,5 1.4 Hz, J5,6a 7.6 Hz, J5,6b 5.5 Hz, H-5), 4.14 (m, 1 H, H-4), 3.86 (dd, 1 H, J3,4 2.1 Hz, J2,3 9.5 Hz, H-3), 3.69 (t, 1 H, J6a,6b 9.2 Hz, H-6a), 3.65 (dd, 1 H, H-6b). 2,3-di-O-benzoyl-4,6-O-benzylidene-D-galactopyranose  EMBED ChemDraw.Document.5.0  HiRes: Calcd. M+Na 499.1369, found 499.1370 The spectrum is superimposition of a and b-isomers (100:15): 8.00-7.30 (m, 15 H, arom.), 5.85-5.78 (m, 3 H, H-1a, H-2a, H-3a), 5.68 (dd, 1 H, J1b,2b 7.9 Hz, J2b,3b 10.2 Hz, H-2b), 5.57 (s, 1 H, bCHPh), 5.56 (s, 1 H, aCHPh), 5.47 (dd, 1 H, J3b,4b 3.7 Hz, H-3b), 4.91 (dd, 1 H, J1a,OH 10.3 Hz, H-1b), 4.64 (d, 1 H, J3a,4a 3.5 Hz, H-4a), 4.58 (d, 1 H, H-4b), 4.42 (dd, 1 H, J5b,6ba 1.6 Hz, J6ba,6bb 12.5 Hz, H-6ba), 4.31 (dd, 1 H, J5a,6aa 1.6 Hz, J6aa,6ab 5.6 Hz, H-6aa), 4.17-4.10 (m, H-5a, H-6ab, H-6bb), 3.72 (s, 1 H, H-5b), 3.67 (d, 1 H, OHb), 2.88 (dd, 1 H, J 1.5 Hz, J 3.3 Hz, OHa). .:>LN~$%&IJKhij>@|~Z \ ^   % & ' D E F c d e jUj+> CJUVmH j`UH*6H*j> CJUVmH jU 5OJQJ565N.8># ( n -P|)^N$d.8># ( n -P|)^Nb15cd # 1 3 < =  & ( * f h j l D F L 89:WXYyz} ,-.LMNO !"?@A}~ j(5Uj> CJUVmHH* j#UjB> CJUVmH jU 5OJQJ565H*6N)01>?^_}~ >@jl ,.0268PRz| H*OJQJOJQJ jDUj> CJUVmH jU565H*6T 2468>@BZ\.0FHNOJQJ H*OJQJ6H*+ 1h/ =!"#$%DdXB  S A? 2G%HEDa!l#D}`!%HEDa!l*< W& x[{tTyǽw_ZI ! bE '@ f !;ZH"0q .vZש`ڮIH;vM5v[Ӗ:I8DZ㶎{I]o\t8􏜬|1ܙ]Q"O)%$@^ xY4Hl(# B">/&)B6z%(k(|f3/W7T@ȇ.e֌vʨUŒZ>ft㵍SƖQNqh2^bѷe]onfͫXy3"t}f@%W='p|F;\qQVet"(`I|>7χtKEyN"Pu^OBC,'Yݘz@,w= E}DxԔ1Qa@IB11ӡv1~ gtҁ^ Wv_ KTIeS<-ƨ\zMI;9>Yy-OGʚ >R'_M->ɨ-ބM@@o >W;/&@;~n;g |"r?+ Vx&NL nm΃ Vs'ǘ7۱?7G2~̛(Q -zMfvX7xv8c4Ƶltj=,_!f nM$^a2ZzM̀ kL<6_O,758{D!o@ ċ *ě ~1@B3 g4 J A@Pc ހX:h6 /)DQ aʵj@lV?z D% *rR#ƌ<ξW1[ *cOp k$ b@2fqDH@ :ep0" #>D=*[" {E7|ћ#_r|_M\Bv D牺6LZ%B$_k yw¢i!ӕiW;0q?*ȡ.!BN 9= .ɱ=} LtgC~FSnl9lXg;L'0;ZzrtCwN˱6M!7 r J\$F%AnQF4\EnM! 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CS ChemDraw DrawingChemDraw Interchange FormatChemDraw.Document.5.09qVjCD0100ChemDraw 5.0BMicrosoft Word - C:\Pavel\Mail\attach\Supporting Information.docw52  B7 $$$$xCONTENTS_1053870891 !mA. 5f@gOle CCompObj D~x@  `  xxfg(dd'`$ArialTimes New Roman. I P ږ` p sh$ " `O3&ffj W           @P    |I' %`BnO~Ky?~K/01+2+3+4+5+6+7A 8A7901:12;23<34=45>05?06@67   A( &`BnO3C7CBCD+E+F+G+H+I+JT KTJLCDMDENEFOFGPGHQCHRCISIJ  sh) '`BnO3@k^kUVW+X+Y+Z+[+\+]g ^g]_VW`WXaXYbYZcZ[dV[eV\f\]  sp% # `Osnnr  }`& $`OBnM^{_khijk+l+m+n+o+p+z qziripsjktklulmvmnwnoxjoyjp  &  s  ڛ  s3+ )`OH+!  "  * (`OH33+# !", *f    C37H42O8 Exact Mass: 614.28797 |- +m     M+Na C37H42NaO8 Exact Mass: 637.27774% !mA. CS ChemDraw DrawingChemDraw Interchange FormatChemDraw.Document.5.09qVjCD0100ChemDraw 5.0BMicrosoft WoObjInfo FCONTENTSG_1053870914!mA. z`{Ole rd - C:\Pavel\Mail\attach\Supporting Information.doct52  B7 $$$$xx@  `  xxfg(dd'`$ArialTimes New RomanQ* (I+ )P, *ږ`- +p. ,shH F `O3&f&f&j/ -W0 .*+1 /+,2 0,-3 1-.4 2./5 3*/6 4@P7 5/68 6 |IK I`BnO~Ky?~KRST+U+V+W+X+Y+Zd [dZ\ST]TU^UV_VW`WXaSXbSYcYZ9 7*8: 8 AL J`BnO3C7Cefg+h+i+j+k+l+mw nwmofgpghqhirijsjktfkuflvlm; 9+:< :shM K`BnO3@k^kxyz+{+|+}+~++ yzz{{||}}~y~y= ;,<> <spI G `Osnnr? =->@ >}`J H`OBnM^{_k++++++ A ?6@B @&C A>BD BsE CBDF DN L `O3&&&G EDFO Mf   C36H38O7 Exact Mass: 582.26175 {vP Nm     M+Na C36H38NaO7 Exact Mass: 605.25152% !mA. CS ChemDraw DrawingChemDraw Interchange FormatChemDraw.Document.5.09qVjCD0100ChemDraw 5.0BMicrosoft WoCompObj~ObjInfoCONTENTS _1053871011!mA. @[፾rd - C:\Pavel\Mail\attach\Supporting Information.doc;Z2  B7 $$$$xx@  `  xxfg(dd'`$ArialTimes New Roman*  #O s1MW 3-Zg s1@w  #n  `O%l m%q M's^           MW   fO# !`BnOMRER+,-+.+/+0+1+2+3= 4=35,-6-.7./8/0901:,1;,2<23  .G( &`BnO0ZJ+=0J>?@+A+B+C+D+E+FP GPFH?@I@AJABKBCLCDM?DN?EOEF   <n) '`BnO>q9e>qQRS+T+U+V+W+X+Yc ZcY[RS\ST]TU^UV_VW`RWaRXbXY  >@w!  `OMAt@<Mu@AMy  &Zg"  `OBn eeqdefg+h+i+j+k+l+v mvenelofgpghqhirijsjktfkufl  G  >$ " `OMA@< @A   U% # `H3XSX & $f    C35H36O7 Exact Mass: 568.24610 3' %m     M+Na C35H36NaO7 Exact Mass: 591.23587%M+3'; !mA. CS ChemDraw DrawingChemDraw Interchange FormatChemDraw.Document.5.09qOle CompObj~ObjInfoCONTENTS VjCD0100ChemDraw 5.0BMicrosoft Word - C:\Pavel\Mail\attach\Supporting Information.doc ;@2  B7 $$$$xx@  `  xxfg(dd'`$ArialTimes New Roman"  #O s1MW 3-Zg s1@w  #n  `O%l m%q M's^           MW   fO `BnOMRER#$%+&+'+(+)+*++5 ,5+-$%.%&/&'0'(1()2$)3$*4*+  .G `BnO0ZJ+=0J678+9+:+;+<+=+>H ?H>@78A89B9:C:;D;<E7<F7=G=>   <n `BnO>q9e>qIJK+L+M+N+O+P+Q[ R[QSJKTKLULMVMNWNOXJOYJPZPQ  7@  `O9M49  &Zg `OBn eeq\]^_+`+a+b+c+d+n en]f]dg^_h_`i`ajabkbcl^cm^d  f    C34H34O6 Exact Mass: 538.23554 ! h     C34H34NaO6 Exact Mass: 561.22531 +'3_1053871078!mA. $ўOle CompObj~ObjInfo      !"#$%&'()*+,-./012345678:;<=>?ABCDEFGIJKLMNOPQRSTUVWXYZ[\]^_`abcdefghijklmnopqrstuvwxyz{|}~ !mA. 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