3-azido-2(S)-methoxy-propanal diethyl acetal → (3R,4S,5S)-6-azido-5-methoxy-1,3,4-trihydroxyhexan-2-one

HRID 991169Notes

Reaction equation

HRID 991169 reaction equation
C(OC(OCC)[C@@H](OC)CN=[N+]=[N-])C.[N:15]([CH2:18][C@H:19]([O:28][CH3:29])[C@H:20]([OH:27])[C@H:21]([OH:26])[C:22](=[O:25])[CH2:23][OH:24])=[N+:16]=[N-:17]>>[N:15]([CH2:18][C@H:19]([O:28][CH3:29])[C@@H:20]([OH:27])[C@@H:21]([OH:26])[C:22](=[O:25])[CH2:23][OH:24])=[N+:16]=[N-:17]

Participants

3

Reactant 2

HCID 233929003-azido-2(S)-methoxy-propanal diethyl acetalHCID 131723539(35,4r,5s)-6-Azido-5-methoxy-1,3,4-trihydroxyhexan-2-one

Product 1

HCID 86758558(3R,4S,5S)-6-azido-5-methoxy-1,3,4-trihydroxyhexan-2-oneYield 38%

Procedure

A solution of 3-azido-2(S)-methoxy-propanal diethyl acetal 25 (832 mg, 4.1 mmol) prepared in the same way as above as for compound 26 from the S-enatiomer was treated in the same manner as described for the R enantiomer. In this case rhamnulose-1-phosphate aldolase was added (0.5 mL, 80 units) and after usual monitoring and work-up, 380 mg (38%) of (3R,4S,5S)-6-azido-5-methoxy-1,3,4-trihydroxyhexan-2-one 27 were obtained. The NMR data were identical to those of 26.

Workup

  1. additionwas treated in the same manner

Sources & evidence

ORD record
ord-4066ea7c0661462e8ef331895df27a7e
Source dataset
uspto-grants-2002_10
Patent number
US06462193B1

Reaction notes

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