(2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanal → Hydrazine

HRID 1719608Notes

Reaction equation

HRID 1719608 reaction equation
O=C[C@@H:3]([C@@H:5]([C@H:7]([C@H:9]([CH3:11])[OH:10])[OH:8])O)O.C1([NH:18][N:19]=C[C@@H]([C@H]([C@H](C)O)O)O)C=CC=CC=1.[NH2:28][C:29]1[N:34]=[C:33]([NH2:35])[C:32]([NH2:36])=[C:31]([OH:37])[N:30]=1>>[NH2:18][NH2:19].[CH3:11][C@H:9]([OH:10])[C@H:7]([OH:8])[C@@H:5]1[NH:36][C:32]2[C:31]([N:30]=[C:29]([NH2:28])[NH:34][C:33]=2[NH:35][CH2:3]1)=[O:37]

Participants

5

Reactant 3

HCID 19233(2R,3R,4S,5S)-2,3,4,5-tetrahydroxyhexanalHCID 686773175-deoxy-L-arabinose-phenylhydrazoneHCID 178508811HCID 178508811, compound

Product 2

HCID 9321HydrazineHCID 178462349(6R)-2-amino-6-[(1R,2S)-1,2-dihydroxypropyl]-5,6,7,8-tetrahydro-1H-pteridin-4-one

Procedure

1',2'-diacyl-L-biopterin of the general formula (III) can be prepared by converting L-rhamnose to an acyl derivative of 5-deoxy-L-arabinose-phenylhydrazone through a 1,1-dialkylsulfonyl-L-rhamnose, reacting the obtained acyl derivative with 2,4,5-triamino-6-hydroxy-pyrimidine to obtain a hydrazine derivative of tetrahydro-L-biopterin and oxidizing the hydrazine derivative, without isolating the intermediate products in the course of reaction from the 1,1-dialkylsufonyl-L-rhamnose to the 1',2'-diacyl-L-biopterin.

Sources & evidence

ORD record
ord-eb6b5b0f8b6a4edab8535d2c57b89a96
Source dataset
uspto-grants-1985_09
Patent number
US04540783

Reaction notes

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