98102-72-8

Upstream product

• 67-64-1 acetone 
• 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 
• 100-39-0 benzyl bromide 
• 115181-73-2 (2S,3R,4S)-3,5-isopropylidenedioxy-2,4-dimethylpentanol 
• 97747-36-9 (4R,2'R,3'S,4'S)-3-(5'-Benzyloxy-3'-hydroxy-2',4'-dimethylpentanoyl)-4-isopropyl-2-oxazolidinone 
• 100837-02-3 (±)-methyl (2R,3S,4S)-5-(benzyloxy)-3-hydroxy-2,4-dimethylpentanoate 
• 79027-28-4 (2S)-3-(benzyloxy)-2-methylpropanal 
• 63930-49-4 (R)-3-(benzyloxy)-2-methylpropan-1-ol 
• 683278-48-0 (4S,5S)-2,2,5-Trimethyl-4-((S)-1-methyl-allyl)-[1,3]dioxane 
• 155417-64-4 (2S,3S,4S)-2,4-Dimethylhex-5-ene-1,3-diol 
• 97805-14-6 (2R,3R,4S)-3,5-Isopropylidenedioxy-2,4-dimethylpentanal 
• 106296-58-6 (2S,3S,4S)-(1-tert-butyldimethylsilanyloxy)-2,4-dimethylhex-5-en-3-ol 
• 97805-13-5 (2S,3S,4S)-3,5-isopropylidenedioxy-2,4-dimethyl-1-pentanol 

Downstream Products

• 81520-11-8 (2R,3S,4S)-5-(benzyloxy)-2,4-dimethylpentane-1,3-diol 
• 683278-53-7 [(2S,3S,4R)-5-Iodo-2,4-dimethyl-3-(2-methyl-propenyloxy)-pentyloxymethyl]-benzene 
• 97690-88-5 (2E,4E,6S,7S,8S)-7-Hydroxy-6,8-dimethyl-9-triphenylmethoxy-2,4-nonadienoic acid 
• 97690-87-4 Methyl (2E,4E,6S,7S,8S)-7-hydroxy-6,8-dimethyl-9-triphenylmethoxy-2,4-nonadienoate 
• 108393-28-8 (2S,3R,4S)-5-benzyloxy-2,3-dimethylpentane-1,4-diol 
• 110672-02-1 (3S,4S,7S)-3-Benzyloxymethyl-7-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-4-vinyl-octan-4-ol 
• 120269-81-0 C₅₇H₈₄O₁₂ 
• 120269-81-0 C₅₇H₈₄O₁₂ 
• 120269-90-1 C₅₈H₈₆O₁₃ 
• 126394-27-2 (E)-(3S,7S)-3-Benzyloxymethyl-7-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-oct-5-en-4-one 
• 53003-10-4 salinomycin 
• 110672-02-1 (3S,4R,7S,8R,9S)-3-benzyloxymethyl-8,10-isopropylidenedioxy-7,9-dimethyl-4-vinyldecan-4-ol 
• 120297-98-5 Methanesulfonic acid (2S,5S)-2-((S)-1-benzyloxymethyl-propyl)-2-hydroxy-5-((4R,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-hexyl ester 
• 110653-53-7 (2S,3R,4S,7S,8S)-8-benzyloxymethyl-1-(4-methoxybenzyloxy)-2,4-dimethyl-7-methyleneoxydecan-3-ol 

Relevant academic research and scientific papers

Stereoselection at the Steady State in Radical Cyclizations of Acyclic Systems Containing One Radical Acceptor and Two Precursors in a 1,5- Relationship under Pseudo-First-Order Conditions

The first example of a successive kinetic resolution of acyclic diastereomeric radical intermediates in a 1,5-relationship under pseudo-first-order conditions is reported. A mechanistic model involves nonselective generation of the radical intermediates followed by different partitioning of these between two different chemical pathways. The "2,5-cis" selectivity in the radical cyclization step arises from transition geometries with the substituents aligned in pseudoequatorial positions.

Absolute structural determination of stevastelin B

Stevastelin B, obtained from a culture of a Penicillium sp. NK374186, is a novel depsipeptide containing three amino acids and 3,5-dihydroxy-2,4-dimethylstearic acid. The stereochemistry of the three amino acids was determined by HPLC analysis, and the re

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.

Synthesis of Enantioenriched Homopropargylic Alcohols through Diastereoselective SE' Additions of Chiral Allenylstannanes to Aldehydes

Allenylstannanes (S)-4 and (R)-4, available in ca. 90percent ee from alkynones 1 through reduction with the LiAlH4-Darvon alcohol or -ent-Darvon alcohol complex, followed by SN2' displacement on the derived mesylates (R)-3 or (S)-3 with Bu3SnLi*CuBr*Me2S, readily add to various aldehydes under Lewis acid catalysis to afford optically active homopropargylic alcohols with good to excellent syn diastereoselectivity.With 2-(benzyloxy)propanal (48), MgBr2-catalyzed reactions are highly stereoselective, affording the syn adduct 49 from the (S)-stannane (S)-4 and the anti adduct 52 from the (R)-stannane (R)-4.BF3-promoted additions give mainly or exclusively the syn adducts 49 and 51.Additions of (S)- and (R)-4 to (R)-3-(benzyloxy)-2-methylpropanal (61) yield the syn adducts 62 and 64 as major or exclusive products.

Chiral Synthesis of Polyketide-derived Natural Products. Part 5. Synthesis of a Chiral Segment Corresponding to the C-1-C-5 Unit of Erythromycin A from D-Glucose

As a right-hand segment with three consecutive chiral centres corresponding to the C-1-C-5 unit of erythromycin A (1), (2S,3R,4S)-3,5-isopropylidenedioxy-2,4-dimethylpentanal (32) was synthesized from D-glucose (5) by application of MPM (4-methoxybenzyl)