Sucrose → HCID 14061412, compound

HRID 2351096Notes

Reaction equation

C(O)[C@H]1O[C@H](O[C@]2(CO)O[C@H](CO)[C@@H](O)[C@@H]2O)[C@H](O)[C@@H](O)[C@@H]1O.[CH2:24]([O:26][C:27]([CH:29]1[C:36](=[O:37])[CH2:35][CH:34]2[CH:30]1[CH2:31][C:32]1([O:41][CH2:40][CH2:39][O:38]1)[CH2:33]2)=[O:28])[CH3:25].CCC(COC(C(N(CC[NH+](C)C)C)=O)(C1C=CC=CC=1)C1C=CC=CC=1)CC.[Cl-]>P([O-])([O-])([O-])=O>[CH2:24]([O:26][C:27]([CH:29]1[C:36](=[O:37])[CH2:35][C@H:34]2[C@@H:30]1[CH2:31][C:32]1([O:38][CH2:39][CH2:40][O:41]1)[CH2:33]2)=[O:28])[CH3:25]

Participants

Conditions

Temperature: 30 °C

Procedure

A solution of sucrose (15 g) in 0.lM phosphate buffer (pH7, 100 ml) was warmed to 30° C., and baker's yeast (7.0 g) was added, then shaken for 15 min at 30° C. An emulsion of (1SR,5RS)-2-ethoxycarbonyl-7,7-ethylenedioxybicyclo[3.3.0]octan-3-one (VIII) (498 mg) in 0.2% Triton X-100 (15 ml) was added and the mixture was shaken at 30° C. Sucrose (10 g) was added after 8 hours and successively sucrose (10 g) and baker's yeast (3.5 g) were added after 24 and 48 hours, then the mixture was shaken for 72 hours. Procedure similar to that of Referential Example 1 gave 109 mg of (1S,5R)-2-ethoxycarbonyl-7,7-ethylenedioxybicyclo-[3.3.0]octan-3-one (IV).

Workup

additionbaker's yeast (7.0 g) was added
stirringthe mixture was shaken at 30° C
stirringthe mixture was shaken for 72 hours

Sources & evidence

ORD record: ord-8e52f6f2ac5c480e87b007ce6ae45a4b
Source dataset: uspto-grants-1989_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04871869

Reaction notes

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