69744-44-1

Upstream product

• 30608-62-9 (S)-(-)-1,2-epoxybutane 
• 82087-38-5 (7S)-4,4-Dimethoxy-1,7-bis(tetrahydropyranyloxy)nonan 
• 74577-87-0 Methyl-2,3,5,6-tetradesoxy-D-glycero-hexofuranose 
• 74577-91-6 (R)-1-[1,3]Dithian-2-ylidene-pentan-3-ol 
• 74577-90-5 Aldehydo-3,5,6-tridesoxy-D-erythro-hexose-trimethylendithioacetal 
• 82087-41-0 Aldehydo-3,5-didesoxy-6-O-(p-tosyl)-2,4-O-isopropyliden-D-erythro-hexose-trimethylendithioacetal 
• 82087-38-5 (7R)-4,4-Dimethoxy-1,7-bis(tetrahydropyranyloxy)nonan 
• 74577-89-2 (7R)-4,4-Trimethylendithio-1,7-bis(tetrahydropyranyloxy)nonan 
• 76495-07-3 (R)-4,4-Trimethylendithio-1,7-nonandiol 
• 161513-89-9 (R)-(-)-Nonane-1,7-diol 
• 149742-03-0 (R)-(+)-6-Iodohex-3-yl acetate 
• 149706-97-8 (S)-(+)-2-<2-O-(p-Tolylsulfonyl)ethyl>tetrahydrofuran 
• 161458-59-9 (R)-(-)-6-Iodo-3-hexanol 
• 51769-31-4 (R)-(-)-2-Ethyltetrahydrofuran 

Downstream Products

• 69744-43-0 (2R,5S)-2-ethyl-1,6-dioxaspiro<4.4>nonane 
• 70427-58-6 (2S,5S)-2-ethyl-1,6-dioxaspiro<4.4>nonane 
• 70427-57-5 (2S,5R)-2-ethyl-1,6-dioxaspiro<4.4>nonane 

Relevant academic research and scientific papers

Dihydro- and Tetrahydrofuran Building Blocks from 1,4:3,6-Dianhydrohexitols. 2. Synthesis of Acetal, Alcohol, Diol, Epoxide, Hydrocarbon, and Lactone Pheromones

The potential of building blocks 1-3 for synthesis of enantiopure substances is illustrated by their transformation to various insect pheromones featuring functionalities specified in the title.A convenient synthesis of building block 3 from sorbitol is described.

Synthesis of spiroacetal pheromones via metalated hydrazones

The synthesis of simple alkyl substituted spiroacetals by α,α'-alkylation of metalated acetone dimethylhydrazone with appropriate electrophiles and subsequent acid catalyzed cleavage and ring closure of the products is described.

Synthesis of Spiroacetals using Organoselenium-mediated Cyclisation Reactions. X-Ray Molecular Structure of (2S,8R)-8-Methyl-2-phenyl-1,7-dioxaspiroundecan-4(R)-ol

Alkenyl hydroxyketones undergo cyclisation via their hemiacetal form, in the presence of N-phenylselenophthalimide (NPSP) and a Lewis acid, to give the corresponding phenylseleno-substituted spiroacetals.Using this methodology the synthesis of trans- and cis-2-methyl-1,6-dioxaspirononane (1), trans- and cis-2-ethyl-1,6-dioxaspirononane (chalcogran)(2), trans- and cis-2-methyl-1,6-dioxaspirodecane(3), trans-7-methyl-1,6-dioxaspirodecane (4), trans-2-methyl-1,7-dioxaspiroundecane (5), and (2S,8R)-8-methyl-2-phenyl-1,7-dioxaspiroundecane-4-one(6) has been achieved, after reductive removal of selenium using Raney-nickel in diethyl ether.Compound (2) is the principal aggregation pheromone from Pityogenes chalcographus (L), whilst compounds (3) and (4) constitute the pheromone components of the common wasp, Paravespula vulgaris.The structure of the spiroacetal (6) was determined as a result of X-ray crystallography of a later derivative, obtained by sodium borohydride reduction of (6).

SPIROACETALS FROM ACETONE AND OXIRANES - A SIMPLE ROUTE TO OPTICALLY ACTIVE 1,6-DIOXASPIRONONANE-PHEROMONES

A new and efficient synthesis of 1,6-dioxaspirononane-spiroacetals, starting from the simple building blocks acetone and oxiranes is described.

Chiral Building Units from Carbohydrates, VI. - Synthesis of (2R,5RS)- and (2S,5RS)-2-Ethyl-1,6-dioxaspirononane (Chalcogran) from D-Glucose

Starting from D-glucose the syntheses of the title compounds (15 and 25) are described.Key compounds are the tetradeoxytrimethylenedithioacetals 11 and 23 which lead by the Corey-Seebach reaction with the THP-blocked 3-bromo-1-propanol to the fully blocked, open-chained products 13 and to the (S)-analogous compound.Mild cleavage of the dithiane group and the THP-protective groups yields after spontaneous cyclisation 15 and 25.The open-chained mono-ol 11 with D-configurated hydroxyl group can be converted into the L-configurated product 22 by esterification with benzoic acid/ triphenylphosphane/ diethyl azodicarboxylate.