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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 272290Generated: October 25, 2026

Water → Dimethyl 7-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]-3-t-butoxycarbonylamino-3-hydroxymethylheptylphosphonate

https://huagongshe.com/reaction/272290

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantTBAF tetrahydrofuranHCID 11078149—
ReactantDimethyl 7-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]-3-t-butoxycarbonylamino-3-t-butyldimethylsiloxymethyl-1-heptenylphosphonateHCID 131727196—
SolventTetrahydrofuranHCID 8028—
ProductDimethyl 7-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]-3-t-butoxycarbonylamino-3-hydroxymethylheptylphosphonateHCID 23094230—

Reaction Steps

The compound of Example 287 was reduced in the same manner as in Reference Example 123 and the resulting compound (107 mg) was dissolved in tetrahydrofuran (5.0 mL). A 1 mol/L TBAF-tetrahydrofuran solution (160 μL) was added dropwise and the mixture was stirred for 3 hours at room temperature. Subsequently, water was added and the reaction mixture was extracted with ethyl acetate. The extract was washed sequentially with water and a saturated aqueous solution of sodium chloride and the organic phase was dried over anhydrous sodium sulfate. The solvent was removed by distillation and the residue was purified on a silica gel column chromatography (ethyl acetate only) to obtain the desired product as a colorless oil (47 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07456157B2
Source datasetuspto-grants-2008_11
ORD IDord-962c50109af24cc18087ea9ddcff22ab
Source noteuspto-grants-2008_11