(2S,3R,4S,5R)-2,3,4,5-Tetrahydroxycyclohexanone → HCID 44511908, compound

HRID 389377Notes

Reaction equation

HRID 389377 reaction equation
[CH2:1]1[C:6](=[O:7])[C@@H:5]([OH:8])[C@H:4]([OH:9])[C@@H:3]([OH:10])[C@@H:2]1O>O>[OH:10][C@@H:3]1[C@@H:4]([OH:9])[C@H:5]([OH:8])[C:6](=[O:7])[CH:1]=[CH:2]1

Participants

3

Reactant 1

HCID 10583108(2S,3R,4S,5R)-2,3,4,5-Tetrahydroxycyclohexanone

Product 1

HCID 44511908HCID 44511908, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.5 g of 2-deoxy-scyllo-inosose synthesized according to the method described in WO 2006/112000 and 100 mg of silica gel (Merck Kieselgel 60) were added to 1 mL of water, and the resulting mixture was heated at 150 degrees centigrade for 2 hours. After the completion of the reaction, a quantitative analysis was carried out using HPLC and as a result, (4S,5R,6S)-4,5,6-trihydroxy-2-cyclohexene-1-one was obtained at a yield of 50%. At this time, 15% of the raw material of 2-deoxy-scyllo-inosose was collected.

Workup

  1. temperaturethe resulting mixture was heated at 150 degrees centigrade for 2 hours
  2. customAfter the completion of the reaction

Sources & evidence

ORD record
ord-1ad790c625984b5c94fbee7eac4fd2ca
Source dataset
uspto-grants-2013_02
Patent number
US08378146B2

Reaction notes

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