HCID 18657616, compound → HCID 44305824, compound

HRID 1492023Notes

Reaction equation

HRID 1492023 reaction equation
[Si](OCCC[C@H]1[C@H](OC(=O)[C@@H](C2C=CC=CC=2)OC)CO[C@H]1C1C=NC=CC=1)(C(C)(C)C)(C)C.[C:35]1([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[CH:40]=[CH:39][C:38]([CH2:41][O:42][C@H:43]2[CH2:47][O:46][C@H:45]([C:48]3[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=3)[C@@H:44]2[CH2:54][CH2:55]/[CH:56]=[CH:57]\[CH2:58][CH2:59][C:60]([OH:62])=[O:61])=[CH:37][CH:36]=1>CO>[C:35]1([C:63]2[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=2)[CH:36]=[CH:37][C:38]([CH2:41][O:42][C@@H:43]2[CH2:47][O:46][C@@H:45]([C:48]3[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=3)[C@H:44]2[CH2:54][CH2:55]/[CH:56]=[CH:57]\[CH2:58][CH2:59][C:60]([OH:62])=[O:61])=[CH:39][CH:40]=1

Participants

4

Reactant 2

HCID 18657616HCID 18657616, compoundHCID 67797893HCID 67797893, compound

Product 1

HCID 44305824HCID 44305824, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(Z)-(2R,3R,4S)-7-[4-(biphenyl-4-ylmethoxy)-2-(3-pyridyl)tetrahydrofuran-3-yl]hept-4-enoic acid having mp 94°-96° C. and [α]D25 =-83.75° (MeOH) is prepared from (2R,3R,4S)-3-(3-t-butyldimethylsilyloxypropan-1-yl)-4-[(R)-(-)-α-methoxyphenylacetoxy]-2-(3-pyridyl)tetrahydrofuran as described for the synthesis of (Z)-(2S,3S,4R)-7-[4-(biphenyl-4-ylmethoxy)-2-(3-pyridyl)tetrahydrofuran-3-yl]hept-4-enoic acid in example 1.

Sources & evidence

ORD record
ord-c9963b0a3fb64407a54ea0ac242228f4
Source dataset
uspto-grants-1994_12
Patent number
US05371096

Reaction notes

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