(S)-5,6-di(nitrooxy)hexanoic acid → (3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 3-(2,3-bis(nitrooxy)propoxy)propanoate

HRID 1676013Notes

Reaction equation

HRID 1676013 reaction equation
[N+]([O:4][C@H:5]([CH2:12][O:13][N+]([O-])=O)[CH2:6][CH2:7][CH2:8][C:9](O)=[O:10])([O-])=O.[N+:17]([O:20][CH:21]([CH2:29][O:30][N+:31]([O-:33])=[O:32])[CH2:22][O:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])([O-:19])=[O:18]>>[N+:17]([O:20][CH:21]([CH2:29][O:30][N+:31]([O-:33])=[O:32])[CH2:22][O:23][CH2:24][CH2:25][C:26]([O:28][C@@H:8]1[CH2:9][O:10][C@@H:6]2[C@H:5]([OH:4])[CH2:12][O:13][C@H:7]12)=[O:27])([O-:19])=[O:18]

Participants

3

Reactant 2

HCID 29923588(S)-5,6-di(nitrooxy)hexanoic acidHCID 866459403-(2,3-Bis(nitrooxy)propoxy)propanoic acid

Product 1

HCID 59509508(3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 3-(2,3-bis(nitrooxy)propoxy)propanoate

Procedure

The title compound was prepared by following the procedure for the synthesis of EXAMPLE 4, except that in Step F the reagent (S)-5,6-di(nitrooxy)hexanoic acid was replaced by 3-(2,3-bis(nitrooxy)propoxy)propanoic acid obtained as described in Oscar Pamies and Jan-E. Backvall, J. Org. Chem. 2002, 67, 1261-1265) and EXAMPLE 10.

Workup

  1. customfor the synthesis of EXAMPLE 4
  2. customobtained

Sources & evidence

ORD record
ord-5bef3531bb1c4ab89b7e45a51ccf0d12
Source dataset
uspto-grants-2011_08
Patent number
US08003811B2

Reaction notes

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