17325-87-0

Upstream product

• 151121-12-9 acetic acid 2-acetoxy-3-benzyloxy-propyl ester 
• 64-19-7 acetic acid 
• 121787-44-8 (-)-1-O-acetyl-3-O-benzylpropane-1,2,3-triol 
• 56552-80-8 (R)-3-benzyloxy-1,2-propanediol 
• 88753-39-3 Benzoic acid (S)-3-benzyloxy-2-methanesulfonyloxy-propyl ester 
• 167076-54-2 (S)-3-(Phenylmethoxy)-1,2-propandiol, 1-Benzoat 
• 14347-83-2 (R)-2,2-dimethyl-4-benzoxymethyl-1,3-dioxolane 
• 100-39-0 benzyl bromide 
• 13071-59-5 3-benzyloxypropan-1,2-diol 
• 185424-20-8 Acetic acid (S)-1-benzyloxymethyl-4,4,4-trifluoro-but-2-ynyl ester 
• 15028-56-5 4-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolane 
• 100-44-7 benzyl chloride 
• 75-36-5 acetyl chloride 
• 154004-19-0 Acetic acid (S)-2-benzyloxy-1-hydroxymethyl-ethyl ester 

Downstream Products

• 17325-85-8 (2S)-3-(benzyloxy)propane-1,2-diol 

Relevant academic research and scientific papers

Efficient chemoenzymatic enantioselective synthesis of diacylglycerols (DAG)

A new efficient chemoenzymatic methodology for the production of 3-O-benzyl-sn-glycerol and 1,2-O-dipalmitoyl-sn-glycerol has been developed. It starts from racemic 1-O-benzylglycerol and is based on the sequential enzymatic acylation-Mitsunobu inversion-enzymatic hydrolysis, which has been performed without isolation of the intermediates. In this way a 70-75% yield of 3-O-benzyl-sn-glycerol with 94-96% ee has been obtained.

Highly Stereoselective Synthesis of Trifluoromethylated Compounds via Ester-Enolate [2,3]-Wittig and [3,3]-Ireland-Claisen Rearrangements

γ-Trifluoromethylated propargylic alcohols have been obtained in optically pure forms via effective enzymatic kinetic resolution and then converted into (E)- or (Z)-allylic alcohols. [2,3]-Wittig rearrangement of the corresponding [[γ-(trifluoromethyl)allyl]oxy]acetic acid methyl esters afforded α-hydroxy-β-(trifluoromethyl)-γ,σ-unsaturated carboxylic acid methyl esters in good yields. The rearrangement of (Z)-substrates proceeded in a highly stereoselective manner to give anti-isomers with E configuration at a newly created olefinic bond via complete chirality transfer. (E)-Substrates, however, showed relatively low stereoselectivities resulting in mixtures of syn- and anti-products. The trifluoromethylated allylic alcohols were also converted into the corresponding α-methoxyacetic acid γ-(trifluoromethyl)allyl esters and evaluated as substrates for [3,3]-Ireland-Claisen rearrangement. (E)-Substrates were efficiently transformed into syn-products while (Z)-substrates exhibited relatively low stereoselectivities. The two complementary methods provide facile routes to highly functionalized trifluoromethyl-containing molecules with a high degree of stereocontrol.

Structure and Synthesis of Petrosynes, New Acetylenic Enol Ether Glycerides from the Okinawan Marine Sponge of the Genus Petrosia

Acetylenic enol ether glycerides, 1 and 3, were found in the Okinawan marine sponge of the genus Petrosia.The plane structures of these glycerides were deduced from spectroscopic analysis.Their complete structures were established by enantioselective total synthesis of all possible stereoisomers using (R)-1-O-benzylglycerol and its (S)-enantiomer, prepared from D-mannitol and L-ascorbic acid, respectively, as chiral building blocks.The synthesis involves the palladium(0)-catalyzed coupling reaction of bromo enol ether 9 with enediyne 21 as a key step.It became evident from the synthesis that the natural product 1 consisted of a mixture of (7R,2'S)-24 (petrosyne Ia) and (7S,2'S)-24 (petrosyne Ib), and the natural product 3 consisted of a mixture of (7R,2'S)-28 (petrosyne IIa) and (7S,2'S)-28 (petrosyne IIb).

Lipase-Catalyzed Enantiomer Selective Hydrolysis of 1,2-Diol Diacetates

Enantiomer selective hydrolysis of racemic 1,2-diol diacetates (rac-2a-h) was investigated by using the inexpensive commercial porcine pancreatic lipase.The hydrolysis proceeds with variable regioselectivity but with moderate to good enantioselectivity yielding a mixture of isomeric monoacetates (3a-h and 4a-h) and unchanged diacetate enantiomers (2a-h).Evidence was found that both monoacetates (3a-h and 4a-h) are formed with the same sense of enantiomer selectivity.

Regio- and enantioselective esterifications of polyoxygenated compounds catalyzed by lipases

The lipase catalyzed esterifications of derivatives of propane-1,2,3-triol and butane 1,2,4-triol in organic solvents have been studied. The influence of several factors (lipase source, organic solvent, additives and structural variations in the substrate

NUCLEOPHILIC DISPLACEMENT REACTIONS OF THE METHANESULFONATES OF THE 1-O-BENZOYL-1,2-, -1,3-, AND -1,4-GLYCOLS

Nucleophilic displacement reactions of the methanesulfonates (8a-c) of the 1-O-benzoyl-1,2-, -1,3-, and -1,4-glycols (7a-c) with potassium acetate in boiling acetic anhydride have been examined.Both benzoyloxy-group participation pathway (path A) and SN2 displacement pathway (path B) have been involved in the 1,2-(8a)- and 1,3-(8b)-substrates to give a mixture of the primary (10a,b) and the secondary (11a,b) acetates with complete inversion of chiralities.On the other hand, only SN2 displacement pathway (path B) has been involved in the 1,4-substrate (8c) to give the secondary acetate (11c) with inversion of the chirality.