74080-50-5

Usage

Uses

Used in the Food Industry:
<2R,3R>-3-methyl-4-penten-2-ol is used as a flavoring agent for enhancing the taste and aroma of various food products. Its unique properties contribute to the creation of complex and appealing flavors, making it a valuable addition to the culinary world.
Used in the Perfume and Fragrance Industry:
<2R,3R>-3-methyl-4-penten-2-ol is also utilized in the production of perfumes and fragrances due to its distinctive scent. It helps in creating long-lasting and pleasant fragrances that are widely appreciated in the perfumery market.
Used in Organic Synthesis:
<2R,3R>-3-methyl-4-penten-2-ol serves as an intermediate in organic synthesis, playing a crucial role in the production of other organic compounds. Its chemical structure allows for further reactions and modifications, making it a versatile building block in the synthesis of a range of chemical products.

Upstream product

• 130540-34-0 B-(Z)-crotylbis(2-isocaranyl)borane 
• 75-07-0 acetaldehyde 
• 71118-65-5 (E)-but-2-en-1-yl diethyl phosphate 
• 75927-49-0 pinacol vinylboronate 
• 72985-58-1 (-)-(1R,2S,3S,4S)-exo-2-exo-3-<(Z)-2-butenylborylenedioxy>-endo-3-phenylbornane 
• 99438-30-9 (Z)-(+)-crotyldiisopinocampheyl borane 
• 99397-92-9 (Z)-(-)-crotylbis(isopinocampheyl)borane 
• 590-18-1 (Z)-2-Butene 
• 856676-03-4 (10S)-(Z)-B-crotyl-10-trimethylsilyl-9-borabicyclo[3.3.2]decane 
• 856676-00-1 (10R)-(Z)-B-crotyl-10-trimethylsilyl-9-borabicyclo[3.3.2]decane 

Downstream Products

• 1213793-24-8 C₄₅H₆₆N₄O₆Si 
• 1213793-23-7 C₄₆H₆₈N₄O₆Si 
• 1070774-58-1 C₄₆H₆₈N₄O₆Si 
• 880766-68-7 (+)-(3R,4R)-4-(4-methoxybenzyl)oxy-3-methylpent-1-ene 

Relevant academic research and scientific papers

CHIRAL SYNTHESIS VIA ORGANOBORANES. 25. B-(Z AND E)-CROTYLBIS(2-ISOCARANYL)BORANES AS VALUABLE REAGENTS FOR THE ASYMMETRIC CROTYLBORATION OF ALDEHYDES

The asymmetric crotylboration of representative aldehydes, RCHO (R = Me, Et-), with B-(Z and E)-crotylbis(2-isocaranyl)boranes (4 and 5) proceeds with remarkably high enantioselectivity (>94-98 percent ee) and diastereoselectivity (>99 percent de) at -78 deg C in ethyl ether.

Versatile Homoallylic Boronates by Chemo-, SN2′-, Diastereo- and Enantioselective Catalytic Sequence of Cu?H Addition to Vinyl-B(pin)/Allylic Substitution

A highly chemo-, diastereo- and enantioselective catalytic method that efficiently combines a silyl hydride, vinyl-B(pin) (pin=pinacolato) and (E)-1,2-disubstituted allylic phosphates is introduced. Reactions, best promoted by a Cu-based complex with a chiral sulfonate-containing N-heterocyclic carbene, are broadly applicable. Aryl-, heteroaryl-, alkenyl-, alkynyl- and alkyl-substituted allylic phosphates may thus be converted to the corresponding homoallylic boronates and then alcohols (after C?B bond oxidation) in 46–91 % yield and in up to >98 % SN2′:SN2 ratio, 96:4 diastereomeric ratio and 98:2 enantiomeric ratio. The reasons why an NHC?Cu catalyst is uniquely effective (vs. the corresponding phosphine systems) and the basis for different trends in stereoselectivity are provided with the aid of DFT calculations.

Synthesis of the C1-C17 macrolactone of tedanolide

The vinylogous Mukaiyama aldol reaction is a useful method to build up complex polyketide structures. It is successfully employed in the synthesis of the C1-C17 macrolactone of tedanolide, a highly cytotoxic marine natural product. These studies present a practical approach toward the total synthesis of tedanolide; it is pursued using the appropriate C13-C23 segment that is introduced by a pivotal aldol reaction to join both hemispheres.

Asymmetric allyl- and crotylboration with the robust, versatile, and recyclable 10-TMS-9-borabicyclo[3.3.2]decanes

The remarkable versatility and selectivity of the 10-(trimethylsilyl)-9- borabicyclo[3.3.2]decanes (10-TMS-9-BBDs) in the allyl- and crotylboration of representative aldehydes are reported. The new reagents are prepared through air-stable crystalline pseudoephedrine borinic ester complexes of the 10-TMS-9-BBDs (4), which are available in 63% overall yield from B-MeO-9-BBN through a simple two-step procedure. These complexes 4 are directly converted to the corresponding B-allyl-10-TMS-9-BBDs (1) with allylmagnesium bromide, which either can be isolated (98%) or used in situ for the allylations. The remarkable enantioselectivity (96 to ≥99% ee) of these reagents in the rapid (3 h), asymmetric allylboration process at -78 °C is only slightly diminished when it is conducted at 25 °C, a phenomenon attributable to its rigid bicyclic structure. In addition to providing the homoallylic alcohols 6 efficiently (68-80%), the procedure also permits the efficient recovery of 4 (68-84%) for the direct regeneration of 1. Alternatively, an oxidative workup procedure can be used for the preparation of 6. The reagent gives predictable stereochemistry and exhibits an extremely high level of reagent control in the allylboration of D-glyceraldehyde acetonide. A simple and efficient procedure has been developed for the preparation of all four geometric and enantiomeric isomers of the B-crotyl-10-TMS-9-BBDs (10) from optically pure enantiomers of B-MeO-10-TMS-9-BBD (3). These reagents 10 also add rapidly (3 h) and efficiently to representative aldehydes at -78 °C, providing ready access to all four of the possible stereoisomers of the β-methyl homoallylic alcohols 12-15 (69-92%) in high dr (≥98:2) and ee (94-99%).