116296-88-9

Upstream product

• 19164-01-3 ((but-2-en-1-yloxy)methyl)benzene 
• 27299-30-5 (E)-((but-2-en-1-yloxy)methyl)benzene 
• 100-39-0 benzyl bromide 
• 50468-21-8 (2S,3S)-2,3-epoxy-1-butanol 
• 58845-50-4 ((2R,3R)-3-methyloxiran-2-yl)methanol 
• 85099-99-6 Benzoic acid (1S,2R)-3-benzyloxy-2-hydroxy-1-methyl-propyl ester 
• 85100-00-1 Benzoic acid (1R,2S)-1-benzyloxymethyl-2-hydroxy-propyl ester 
• 85099-93-0 Benzoic acid (1R,2S)-1-benzyloxymethyl-2-(toluene-4-sulfonyloxy)-propyl ester 
• 79413-88-0 Toluene-4-sulfonic acid (1S,2R)-3-benzyloxy-2-hydroxy-1-methyl-propyl ester 

Downstream Products

• 1373047-75-6 (2S,3R,4Z)-1-(benzyloxy)-3-methyl-4-hexen-2-ol 
• 1373047-77-8 (2S,3S,4S,5R)-1-benzyloxy-4,5-epoxy-3-methylhexan-2-ol 
• 642993-55-3 (2S,3R,4R)-1-(benzyloxy)-3,5-dimethylhexane-2,4-diol 
• 642993-59-7 (2S,3R,4R)-1-benzyloxy-2,4-bis(tert-butyldimethylsiloxy)-3,5-dimethylhexane 
• 116212-90-9 (5S,6S)-7-Benzyloxy-6-hydroxy-5-methyl-4-oxo-heptanoic acid methyl ester 
• 112482-39-0 4-(benzyloxy)-3-fluorobutan-2-ol 
• 112482-38-9 1-(benzyloxy)-3-fluorobutan-2-ol 

Relevant academic research and scientific papers

Sensing remote chirality: Stereochemical determination of β-, γ-, and δ-chiral carboxylic acids

Determining the absolute stereochemisty of small molecules bearing remote nonfunctionalizable stereocenters is a challenging task. Presented is a solution in which appropriately substituted bis(porphyrin) tweezers are used. Complexation of a suitably derivatized β-, γ-, or δ-chiral carboxylic acid to the tweezer induces a predictable helicity of the bis(porphyrin), which is detected as a bisignate Cotton Effect (ECCD). The sign of the ECCD curve is correlated with the absolute stereochemistry of the substrate based on the derived working mnemonics in a predictable manner.

Concise epoxide-based synthesis of the C14-C25 bafilomycin A1 polypropionate chain

An efficient nonaldol convergent synthesis of the C14-C25 polyketide fragment of bafilomycin A1 was completed in 16% overall yield and 8 steps in its longest linear sequence. This synthesis highlights the formation of the key fragments using a

Bicyclo-octane and bicyclo-nonane derivatives, processes for their preparation and their use as herbicides

Bicyclo-octane and bicyclo-nonane derivatives are described having herbicidal and plant growth regulating properties. The derivatives are based on the general formula

REACTION OF DIANIONS DERIVED FROM β-KETOESTERS WITH EPOXIDES - UTILITY IN THE PREPARATION OF SYNTHETICALLY USEFUL TETRAHYDROFURANS.

Presented here are several examples which demonstrate that ether substituents α- or β- to an epoxide ring can be tolerated in the ring-opening reaction with β-keto ester dianions.Subsequent acid-promoted cyclisation of the γ-hydroxy β-ketoesters then leads to synthetically useful tetrahydrofurans, as demonstrated by application of this approach to the preparation of (+/-)-methyl nonactate and (+/-)-methyl 8-epi-nonactate.

Regioselective Opening of Simple Epoxides with Diisopropylamine Trihydrofluoride

Treatment of benzyl ether derivatives of simple aliphatic epoxy alcohols with diisopropylamine trihydrofluoride gave mixtures of the corresponding fluorohydrins in good yields.Steric hindrance is a major factor in determining the regioselectivity of epoxide opening, although electronic effects cannot be ignored.Electronic effects are more dominant with pyridine polyhydrofluoride.

SYNTHESIS OF THE ENANTIOMERIC FORMS OF CIS AND TRANS 1-BENZYLOXY-2,3-EPOXY BUTANE AND OF (3S,4S) 4-METHYL-3-HEPTANOL

The C4 erythro and threo diols (7) and (8) are converted either into the chiral epoxides (13) and (15) or into the enantiomers (14) and (16); the epoxide (13) is used as chiral synthon for the preparation of (3S,4S) 4-methyl-3-heptanol (21).