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354  16 Aldolases as Catalyst for the Synthesis of Carbohydrates and Analogs

          Table 16.1  (Continued)

          Entry  R 1                      R 2      Product  FSA w-t  FSA A129S  TalB F178Y

          11    CH Ph                     CH         46b      70       —        —
                   2                        3
          12    CH Ph                     CH OH      46c      77       —        —
                   2
                                            2
          13    CH Cl                     CH OH      47c      84       —        —
                                            2
                   2
          14    CH Br                     CH OH      48c      84       —        —
                   2                        2
          15    (CH ) SCH 3               CH OH      49c      —        67       —
                                            2
                   2 2
          16    CH OBn                    CH         50b    95, 71 a   —        —
                   2                        3
          17    CH OBn                    CH OH      50c      35     60 (98) d  —
                                            2
                   2
          18    CH CH(OCH )               CH         61b      98 b     —        —
                   2      3 2               3
          19    (±)-CH(OH)CH OBn          H          52a      65 a     —        —
                           2
          20    CH OH                     H          53a      67 a     —        —
                   2
          21    CH OH                     CH 3       53b    >98, 51 a  70       —
                   2
          22    CH OH                     CH OH      53c      nr     80, 42 a  44 (90) c
                   2                        2
          23    (S)-CH(OH)CH 3            H          54a    >98, 50 a  —        nd
          24    (S)-CH(OH)CH              CH         54b     >75       —      >25<75
                           3                3
          25    (S)-CH(OH)CH              CH OH      54c     <25       —       >75
                           3                2
          26    (S)-CH(OH)CH 3            CH CH 3    54d    >25<75     —        nr
                                            2
          27    (R)-CH(OH)CH              CH         —        nr       —        nr
                           3                3
          28    (R)-CH(OH)CH 3            CH OH      —        nr       —      >25<75
                                            2
          29    (R)-CH(OH)CH              CH CH      —        nr       —        nr
                           3                2  3
          30    (CH ) OH                  CH 3       55b    >25<75     —       <25
                   3 2
          31    (CH ) OH                  CH OH      55c     <25       —      >25<75
                   3 2                      2
          32    (CH ) OH                  CH CH 3    55d    >25<75     —        nr
                   3 2
                                            2
          33    (R)-CH(OH)CH OPO  2−      H          56a      87       —        —
                           2   3
          34    (R)-CH(OH)CH OPO 3 2−     CH 3       56b      95       —        —
                           2
          35    (R)-CH(OH)CH OPO  2−      CH OH      56c      —        80       —
                           2   3            2
          36    (R)-CH(OH)CH OPO 3 2−     CH CH 3    56d      94       —        —
                           2
                                            2
          37    CH CH OH                  CH         57b     >75       —      >25<75
                   2  2                     3
          38    CH CH OH                  CH OH      57c    >25<75     —       >75
                   2  2                     2
          39    CH CH OH                  CH CH 3    57d     >75       —        nr
                   2
                                            2
                      2
          40    (R)-CH(OH)CH OH           H          58a      nd       38       nd
                           2
          41    (R)-CH(OH)CH OH           CH 3       58b     >75     86, 68 a  >25<75
                           2
          42    (R)-CH(OH)CH OH           CH OH      58c     <25     81, 67 a  57 (94) c
                           2                2
          43    (R)-CH(OH)CH OH           CH CH 3    58d     >75       —        nr
                                            2
                           2
          44    (S)-CH(OH)CH OH           CH         59b     >75       —       >75
                           2                3
          45    (S)-CH(OH)CH OH           CH OH      59c     <25       —      48 (99) c
                           2
                                            2
          46    (S)-CH(OH)CH OH           CH CH      59d     >75       —        nr
                           2                2  3
          47    (S)-CH(OH)(R)-CH(OH)CH OH  CH 3      60b    90, 60 a   —        —
                                   2
         Conversions and isolated yields obtained with FSA and TalB catalysts.
          a
          Isolated yields, nr: no reaction, empty: no data found.
          b Immobilized FSA [36a].
          c                F178Y/R181E
          Reactions catalyzed by TalB  [32f].
          d Reaction catalyzed by FSA A129S/A165G .
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