(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → HCID 14061412, compound

HRID 2351097Notes

Reaction equation

HRID 2351097 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:13](=[O:14])[CH2:12][CH:11]2[CH:7]1[CH2:8][C:9]1([O:18][CH2:17][CH2:16][O:15]1)[CH2:10]2)=[O:5])[CH3:2].O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O>>[CH2:1]([O:3][C:4]([CH:6]1[C:13](=[O:14])[CH2:12][C@H:11]2[C@@H:7]1[CH2:8][C:9]1([O:15][CH2:16][CH2:17][O:18]1)[CH2:10]2)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 14061410HCID 14061410, compound

Product 1

HCID 14061412HCID 14061412, compoundYield 20%

Procedure

Using Saccharomyces uvarum IFO 1225 cultivated similarly to Example 3, and 504 mg of (1SR,5RS)-2- ethoxycarbonyl-7,7-ethylenedioxybicyclo[3.3.0]octan-3-one (VIII), reaction was initiated in a similar procedure as mentioned in Referential Example 3. 10 g of glucose after 4 hours, 5 g after 19 hours, and 10 g after 153 hours were added and shaken for 167 hours. Aftertreatment of the reaction mixture in a similar manner as described in Example 3 gave 101 mg of (1S,5R)-2-ethoxycarbonyl-7,7-ethylenedioxybicyclo[3.3.0]octan-3-one (IV).

Workup

  1. addition10 g after 153 hours were added

Sources & evidence

ORD record
ord-63a993329b514dc29993e9a74cae4738
Source dataset
uspto-grants-1989_10
Patent number
US04871869

Reaction notes

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