Ethanethiol → 5-deoxy-L-arabinose-phenylhydrazone

HRID 1719609Notes

Reaction equation

HRID 1719609 reaction equation
O.O=C[C@@H:4]([C@@H:6]([C@H:8]([C@H:10]([CH3:12])[OH:11])[OH:9])[OH:7])O.C(S)C.CCSC(SCC)[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C.O=C[C@@H]([C@H]([C@H](C)O)O)O.CCS(C(S(CC)(=O)=O)[C@H](O)[C@H](O)[C@@H](O)[C@@H](O)C)(=O)=O.[C:61]1([NH:67][NH2:68])[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1>>[C:61]1([NH:67][N:68]=[CH:4][C@@H:6]([C@H:8]([C@H:10]([CH3:12])[OH:11])[OH:9])[OH:7])[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1

Participants

7

Reactant 6

HCID 6343EthanethiolHCID 7516PhenylhydrazineHCID 117080645-Deoxy-L-arabinose2×HCID 13420528(2R,3R,4S,5S)-1,1-Bis(ethylsulfonyl)hexane-2,3,4,5-tetraolHCID 20849066Rhamnose monohydrateHCID 25209258L-Rhamnose diethyl mercaptal

Product 1

HCID 686773175-deoxy-L-arabinose-phenylhydrazone

Procedure

The compound (II) can be prepared by a similar process to the process for preparing 1',2'-diacetyl-L-biopterin [Bernard Schircks, Jost H. Bieri and Max Viscontini, Helvetica Chimica Acta, 60(1), 211 (1977)]. According to the process, L-rhamnose hydrate is reacted with ethanethiol. The obtained L-rhamnose-diethylmer-captal is converted to 5-deoxy-L-arabinose through 1,1-diethylsulfonyl-L-rhamnose. 5-Deoxy-L-arabinose is reacted with phenylhydrazine to obtain 5-deoxy-L-arabinose-phenylhydrazone. 5-Deoxy-L-arabinose-phenyl-hydrazone is reacted with an acylating agent. The obtained 2,3,4-triacyl-5-deoxy-L-arabinose-phenylhyrazone is reacted with 2,4,5-triamino-6-hydroxy-pyrimidine dihydrochloride, and then oxidized with an oxidizing agent such as iodine to obtain a 1',2'-diacyl-L-biopterin. L-Biopterin can be obtained by deacylation of the 1',2'-diacyl-L-biopterin.

Sources & evidence

ORD record
ord-27b385f2117845b7967a46597f49917b
Source dataset
uspto-grants-1985_09
Patent number
US04540783

Reaction notes

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