105816-26-0

Basic information

• Product Name: 5-(benzyloxy)-2,4-dimethyl-1,3-pentanediol
• Synonyms: 5-(benzyloxy)-2,4-dimethyl-1,3-pentanediol
• CAS NO: 105816-26-0
• Molecular Weight: 238.327
• Mol File: 105816-26-0.mol

Chemical Properties

• CAS DataBase Reference: 5-(benzyloxy)-2,4-dimethyl-1,3-pentanediol(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(benzyloxy)-2,4-dimethyl-1,3-pentanediol(105816-26-0)
• EPA Substance Registry System: 5-(benzyloxy)-2,4-dimethyl-1,3-pentanediol(105816-26-0)

Safety Data

• Hazardous Substances Data: 105816-26-0(Hazardous Substances Data)

Upstream product

• 18245-72-2 S-phenylthiopropionate 
• 74130-31-7 3-(benzyloxy)-2-methylpropanal 
• 136788-16-4 (2E,4R)-1-benzyloxy-2,4-dimethyl-5-ethenyloxy-2-pentene 
• 102146-12-3 (2R,3R,4R)-5-Benzyloxy-3-hydroxy-2,4-dimethyl-pentanethioic acid S-tert-butyl ester 
• 79026-61-2 (R)-3-benzyloxy-2-methylpropanal 
• 102146-12-3 (2R,3S,4S)-5-Benzyloxy-3-hydroxy-2,4-dimethyl-pentanethioic acid S-tert-butyl ester 
• 102146-12-3 (2R,3R,4S)-5-Benzyloxy-3-hydroxy-2,4-dimethyl-pentanethioic acid S-tert-butyl ester 
• 171019-26-4 Acetic acid (2S,3R,4R)-5-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-pentyl ester 
• 38614-40-3 2,4-dimethyl-penta-1,4-dien-3-ol 
• 127808-52-0 tert-butyl((2,4-dimethylpenta-1,4-dien-3-yl)oxy)dimethylsilane 
• 135067-25-3 (2R,3S,4S)-2,4-dimethyl-1,3,5-tris(trimethylsiloxy)pentane 
• 135067-27-5 (R)-2-((2R,3S,6S,7S,10R)-7-Isopropyl-3,10-dimethyl-1,5-dioxa-spiro[5.5]undec-2-yl)-propan-1-ol 
• 127808-53-1 (2R,3s,4S)-3-[(tert-butyl-dimethylsilyl)oxy]-2,4-dimethylpentane-1,5-diol 
• 94842-97-4 (2SR,3SR,4RS)-2,4-dimethylpentane-1,3,5-triol 

Downstream Products

• 135211-99-3 (2S,3R,4R)-5-(benzyloxy)-2,4-dimethyl-1,3-pentanediol acetonide 

Relevant articles and documents

Synthesis of polypropionate subunits from cyclopropanes

The oxymercuration-reductive demercuration of several cyclopropanealkanol or their derivatives bearing adjacent stereocenters has been investigated in order to synthesize polypropionate subunits. The crucial importance of the ester protecting group for th

Stereocontrol in organic synthesis using silicon-containing compounds. Studies directed towards the synthesis of ebelactone A

Several approaches to the synthesis of ebelactone A 2 are described, culminating in the synthesis of the benzenesulfonate of 2-epi-ebelactone A 161. All the approaches were based on three fragments A, B and C, originally defined in general terms in Scheme 1, but eventually used as the aldehyde 72, the allenylsilane 3 and the aldehyde 139, respectively. They were joined, first B with C, and then B+C with A. In the main routes to fragments A and C, the relative stereochemistry was controlled by highly stereoselective enolate methylations 66 → 67, 68 → 69, and 135 → 136, in each case anti to an adjacent silyl group, and by a highly stereoselective hydroboration of an allylsilane 137 → 138, also anti to the silyl group. The hydroxyl groups destined to be on C-3 and C-11 were unmasked by silyl-to-hydroxy conversions 69 → 70 and 138 → 139 with retention of configuration. The stereochemistry created in the coupling of fragment B to C was controlled by the stereospecifically anti SE2′ reaction between the enantiomerically enriched allenylsilane 3 and the aldehyde 139. The double bond geometry was controlled by syn stereospecific silylcupration 148 → 151, and preserved by iododesilylation 151 → 152 of the vinylsilane with retention of configuration, and Nozaki-Hiyama-Kishi coupling with the aldehyde 72 gave the whole carbon skeleton 153 of ebelactone A with the correct relative configuration, all of which had been controlled by organosilicon chemistry. In the steps to remove the superfluous allylic hydroxyl, an intermediate allyllithium species 156 abstracted the proton on C-2, and its reprotonation inverted the configuration at that atom. Other routes to the fragments A and C were also explored, both successful and unsuccessful, both silicon-based and conventional, and a number of unexpected side reactions were investigated.

Synthesis of stereotriads by oxymercuration of substituted cyclopropylcarbinols.

[structure: see text] Cyclopropylcarbinol derivatives bearing an adjacent methyl-substituted stereocenter and a remote beta-hydroxy group protected as a pivalate underwent anchimerically assisted regio- and diastereoselective oxymercurations, affording af

Enzymatic desymmetrization of meso(anti-anti)-2,4-dimethyl-1,3,5-pentanetriol

The stereoselective acetylation of meso-3-(tert-butyldimethylsiloxy)-2,4-dimethyl-1,5-pentanediol by vinyl acetate in the presence of Candida rugosa lipase in organic medium gave the corresponding (2R, 3R, 4S) mono ester in high enantiomeric purity (ee =

Stereoselective acetalization of 1,3-alkanediols controlled by intramolecular van der Waals attractive interactions and its application to an enantiodifferentiating transformation of σ-symmetric 1,3,5-pentanetriols

Acetalization reactions of racemic bis(trimethylsilyl) ethers (R1R2CHCH(OTMS)CH(R3)CH2OTMS) with racemic menthone, under thermodynamically controlled conditions, stereoselectively give spiroacetal 2 (in which the substituent R1R2CH- is attached to the carbon adjacent to the axial oxygen atom with respect to the menthane ring) in preference to the diastereomeric spiroacetal 3 (in which the substituent is attached to the carbon adjacent to the equatorial oxygen atom). Correlation between the stereoselectivities and the structures of the spiroacetals as well as the higher stereoselectivities observed in the related acetalization with 7,7,7-trimethylmenthone indicates that the preferential formation of spiroacetal 2 of a folded structure is a result of intramolecular attractive interactions between the menthane moiety and the substituent attached to the 1,3-dioxane ring. Molecular mechanics (MM2) calculations give satisfactory agreement with experiments and provide support for the operation of the van der Waals attractive interaction as the most important factor determining the stereoselectivities. The stereoselective acetalization with l-menthone is successfully applied to a novel enantiodifferentiating transformation of σ-symmetric 1,3,5-pentanetriols (HOCH2CHRCH(OH)CHRCH2OH; R = Me or H). The reaction provides an efficient and straightforward route to chiral menthonide derivatives 13a-c, which can be utilized as versatile chiral building blocks.

Stereoselective Total Synthesis of (+/-)-Invictolide. An Efficient Preparation of a Trisubstituted δ-Lactone from Aldol Precursors

The stereoselective total synthesis of (+/-)-invictolide (1), a component of the queen recognition pheromone of Solenopsis invicta, is described.The TiCl4-mediated addition of silyl ketene thioacetal 8 to (+/-)-3-(benzyloxy)-2-methylpropionaldehyde afford

Diastereoselective Synthesis of 2,3-anti-5-Benzyloxy-2,4-dimethyl-1,3-pentanediols via Cyclic Hydroboration

The treatment of (2E,4S)- and (2Z,4S)-1-benzyloxy-5-ethenyloxy-2,4-dimethyl-2-pentene with borane both with and without a catalytic amount of Rh(Ph3P)3Cl gave 2,3-anti-3,4-anti-(2R,3R,4S)- and 2,3-anti-3,4-syn-(2R,3R,4R)-5-benzyloxy-2,4-dimethyl-1,3-penta

LEWIS ACID MEDIATED ALDOL CONDENSATIONS USING THIOESTER SILYL KETENE ACETALS

BF3-OEt2 mediated thioester silylketene acetal additions to aldehydes are stereoconvergent and give high anti-syn ratios and good chemical yields.An acyclic transition state model was hypothesized in order to account for the observed selectivity.Theoretic

STEREOSELECTIVE ALDOL CONDENSATIONS VIA ALKENYLOXY DIALKYOXYBORANES: SYNTHETIC APPLICATIONS USING THIOESTERS.

A detailed investigation of the enolization of phenyl thiopropionate with ethylenechloroboronate (ECB) and diisopropylethylamine (DPEA) and the subsequent aldol condensations of these enolates was conducted.Alkenyloxy dialkoxyboranes derived from thioesters were found to be stereoconvergent: both Z and E enolates give syn aldol condensation products.The thioester additions to chiral aldehydes were studied.Internal selectivity (syn) was usually very high, while the relative stereoselectivity ranged from poor to good, depending on the specific aldehyde used.The aldol products were transformed to known compounds for correlation.