Trifluoroacetic acid → HCID 18755202, compound

HRID 1085640Notes

Reaction equation

HRID 1085640 reaction equation
[Si]([O:8][CH2:9][CH2:10][S:11]([C:14]1[C:15]([O:40][CH2:41][CH2:42][CH3:43])=[C:16]([O:38][CH3:39])[CH:17]=[C:18]([C:20](=O)[CH2:21][CH2:22][C:23]([C:25]2[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=2)=[O:24])[CH:19]=1)(=[O:13])=[O:12])(C(C)(C)C)(C)C.[Si](OCCS(C1C(OCCC)=C(OC)C=C([C@@H](O)CCC(=O)C2C=C(OC)C(OC)=C(OC)C=2)C=1)(=O)=O)(C(C)(C)C)(C)C.[BH4-].[Na+].C(O)(C(F)(F)F)=O.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(Cl)(Cl)Cl.CO>[OH:8][CH2:9][CH2:10][S:11]([C:14]1[C:15]([O:40][CH2:41][CH2:42][CH3:43])=[C:16]([O:38][CH3:39])[CH:17]=[C:18]([CH:20]2[CH2:21][CH2:22][CH:23]([C:25]3[CH:30]=[C:29]([O:31][CH3:32])[C:28]([O:33][CH3:34])=[C:27]([O:35][CH3:36])[CH:26]=3)[O:24]2)[CH:19]=1)(=[O:13])=[O:12]

Participants

9

Reactant 5

HCID 6422Trifluoroacetic acidHCID 2724141Tetrabutylammonium FluorideHCID 4311764Sodium borohydrideHCID 15718036HCID 15718036, compoundHCID 15718044HCID 15718044, compound

Product 1

HCID 18755202HCID 18755202, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1-(5-(2-t-butyldimethylsilyloxyethylsulfonyl)-4-n-propoxy-3-methoxyphenyl)-4-(3,4,5-trimethoxyphenyl) butane-1,4-dione from step A is stereospecifically reduced with (S)-BINAL-H (J. Am. Chem. Soc. 1984, 106, 6709) to 1-(5-(2-t-butyldimethylsilyloxyethylsulfonyl)-4-n-propoxy-3-methoxyphenyl)-4-oxo-4-(3,4,5-trimethoxyphenyl)-(1S)-butanol (step A'). This compound is reduced (NaBH4, THF, MeOH), cyclized (TFA, CHCl3), desilylated (n-Bu4NF, THF), and purified by chromatography on silica gel using procedures similar to those in step D to give (-)-(2S,5S)-2-(5-(2-hydroxyethylsulfonyl)-4-n-propoxy-3-methoxyphenyl -5-(3,4,5-trimethoxyphenyl)tetrahydrofuran.

Workup

  1. custompurified by chromatography on silica gel using procedures similar to those in step D

Sources & evidence

ORD record
ord-5b44931c4e74429b9ee36ad29c140db1
Source dataset
uspto-grants-1991_04
Patent number
US05010100

Reaction notes

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