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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1109426Generated: November 1, 2026

(2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol tert-butyldimethylsilyl ether → (2R,3R)-4-benzyloxy-1-tert-butyldimethylsilyloxy-3-(3-tolylmethyl)-2-butanol

https://huagongshe.com/reaction/1109426

Reaction equation

Participants

RoleNameHCIDCharge
Reactant(2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol tert-butyldimethylsilyl etherHCID 15708218—
ReactantHCID 178425036HCID 178425036—
Product(2R,3R)-4-benzyloxy-1-tert-butyldimethylsilyloxy-3-(3-tolylmethyl)-2-butanolHCID 53649730—

Reaction Steps

325 mg of (2S,3S)-4-benzyloxy-2,3-epoxy-1-butanol tert-butyldimethylsilyl ether obtained in Example 53, was subjected to Grignard reaction in the same manner as in Example 53 by using 3-tolylmethyl magnesium bromide (0.8M diethyl ether solution). The product was purificated by silica gel column chromatography to obtain 210 mg of (2R,3R)-4-benzyloxy-1-tert-butyldimethylsiloxy-3-(3-tolylmethyl)-2-butanol as colorless oily substance.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05319082
Source datasetuspto-grants-1994_06
ORD IDord-3bd3cd5a80804823b7fa98e2ca988783
Source noteuspto-grants-1994_06