69056-12-8

Basic information

• Product Name: (R)-2-[(3R,5S,6S)-3,5-Dimethyltetrahydro-2-oxo-2H-pyran-6-yl]propionic acid
• Synonyms: (+)-Prelog-Djerassi lactonic acid;(2R)-2-(3,4,5,6-Tetrahydro-3β,5β-dimethyl-6-oxo-2H-pyran-2α-yl)propionic acid;(2S,3S,5R,αR)-Tetrahydro-α,3,5-trimethyl-6-oxo-2H-pyran-2-acetic acid;(R)-2-[(3R,5S,6S)-3,5-Dimethyltetrahydro-2-oxo-2H-pyran-6-yl]propionic acid;Prelog-Djerassi lactone
• CAS NO: 69056-12-8
• Molecular Formula: C₁₀H₁₆O₄
• Molecular Weight: 0
• Mol File: 69056-12-8.mol
• Article Data: 25

Chemical Properties

• Melting Point: 124-125°
• Boiling Point: 380.2°C at 760 mmHg
• Flash Point: 150.2°C
• Appearance: /
• Density: 1.107g/cm³
• Vapor Pressure: 7.81E-07mmHg at 25°C
• Refractive Index: 1.461
• CAS DataBase Reference: (R)-2-[(3R,5S,6S)-3,5-Dimethyltetrahydro-2-oxo-2H-pyran-6-yl]propionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-[(3R,5S,6S)-3,5-Dimethyltetrahydro-2-oxo-2H-pyran-6-yl]propionic acid(69056-12-8)
• EPA Substance Registry System: (R)-2-[(3R,5S,6S)-3,5-Dimethyltetrahydro-2-oxo-2H-pyran-6-yl]propionic acid(69056-12-8)

Safety Data

• Hazardous Substances Data: 69056-12-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H16O4/c1-5-4-6(2)10(13)14-8(5)7(3)9(11)12/h5-8H,4H2,1-3H3,(H,11,12)/t5-,6+,7+,8-/m0/s1

Upstream product

• 546-67-8 lead(IV) tetraacetate 
• 64-19-7 acetic acid 
• 6036-25-5 narbomycin 
• 19721-56-3 picromycin 
• 72367-05-6 methyl <2S-<2α(S^*),3β,5β>>-tetrahydro-α,3,5-trimethyl-6-oxo-2H-pyran-2-acetate 
• 82917-28-0 (3R,5S,6S)-tetrahydro-3,5-dimethyl-6-<(1S)-1-methyl-2-propenyl>-2H-pyran-2-one 
• 79607-42-4 2-((2S,3S,5R)-6-Hydroxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-propionaldehyde 
• 81310-01-2 (R)-2-((2S,3S,5R,6S)-6-Hydroxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-propionic acid 
• 120161-12-8 (3R,5S,6S,7S)-6-<(tert-butyldimethylsilyl)oxy>-3,5,7-trimethylcycloheptene 
• 82507-36-6 (4R,5S)-3-[(R)-2-((2S,3S,5R)-3,5-Dimethyl-6-oxo-tetrahydro-pyran-2-yl)-propionyl]-4-methyl-5-phenyl-oxazolidin-2-one 
• 103563-43-5 (3R,5S,6S)-6-((E)-(S)-4-Benzyloxymethoxy-1-methyl-but-2-enyl)-3,5-dimethyl-tetrahydro-pyran-2-one 
• 92737-89-8 (2S,3S,6R,7S,8S,10R)-7-Hydroxy-2,3,6,8,10-pentamethyl-1,4-dioxa-cycloundecane-5,11-dione 
• 81060-21-1 (3R,5S)-Tetrahydro-3,5-dimethyl-6-<1-methyl-2-propenyl>-2H-pyran-2-on 
• 82898-97-3 (3S,4S,5S,7R)-4-Acetoxy-3,5,7-trimethyl-1,8-nonadien 

Downstream Products

• 945-06-2 (S)-2-((2R,3R,5R)-3,5-Dimethyl-6-oxo-tetrahydro-pyran-2-yl)-propionic acid 
• 945-06-2 (R)-2-((2R,3R,5R)-3,5-Dimethyl-6-oxo-tetrahydro-pyran-2-yl)-propionic acid 
• 77405-47-1 (3R,5S,6S)-6-[(1S,2S,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-5-cyclohexyl-2-hydroxy-1,3-dimethyl-4-oxo-pentyl]-3,5-dimethyl-tetrahydro-pyran-2-one 

Relevant articles and documents

A SHORT AND STEREOSELECTIVE SYNTHESIS OF THE (+/-) PRELOG-DJERASSI LACTONIC ACID

Reaction of meso-4-carbomethoxy-2-methylpentanal (1) with crotyltri-n-butyltin at -78 deg C in the presence of 1 eq BF3*OEt2, followed by the lactonization with BF3*OEt2, gave 6-(1-methylallyl)-3,4,5,6-tetrahydro-3,5-dimethyl-2-pyranone (2a) with the correct stereochemistry (erythro, anti-Cram) in 92percent yield, which was converted to the title compound (3) in 85percent yield upon the ozonolytic cleavage of the double bond.

Enantioselective synthesis of the Prelog-Djerassi lactonic acid via group-selective aldolization/desymmetrization of a meso dialdehyde with a chiral N-propionylsultam

The group-selective aldolization/desymmetrization of meso dialdehyde 5 with a borylenolate derived from N-propionylbornanesultam ent-2 yields very efficiently lactols 6 with simultaneous generation of four stereogenic centers. Oxidation (6→7) followed by saponification of the sultam moiety (7→4) provided the Prelog-Djerassi lactonic acid 4 in a three step sequence in 61-71% overall yield.

-

-

Stereocontrol in organic synthesis using silicon-containing compounds. A synthesis of the (±)-Prelog-Djerassi lactone

Each of the relative stereochemical relationships present in the Prelog-Djerassi lactone 34 was set up by a stereocontrolled reaction based on the presence of a silyl group. These were the enolate protonation 3→4 of a β-silyl ester, the enolate alkylation 11→12 of a β-silyl ester, silyl-to-hydroxy conversion with retention of configuration 13→14, and stereospecifically anti protodesilylation of the allylsilanes 26 and 27 giving largely the alkene 28. These allylsilanes had themselves been prepared in a stereocontrolled, convergent synthesis from the allylic acetates 24 and 25, providing thereby a general solution to the controlled synthesis of a new stereogenic centre relative to a resident centre without regard to their distance apart, except insofar as it influences a necessary separation of diastereoisomers (18 and 19 in this case). Using the opposite double bond geometries, the allylic acetates 29 and 30 gave the complementary pair of allylsilanes 31 and 32, which underwent stereospecifically anti protodesilylation to give largely the alkene 33 diastereoisomeric to 28 at C-6. The alkenes 28 and 33 were converted into the Prelog-Djerassi lactonic acid 34 and its C-6 epimer 35, respectively.

Synthesis of the Prelog-Djerassi Lactone and Protomycinolide IV Based on the Stereospecific Methylation of γ,δ-Epoxy Acrylates by Trimethylaluminum

The Prelog-Djerassi lactone, a key intermediate for the synthesis of several medicinally important macrolide antibiotics, and protomycinolide IV, a 16-membered macrolide, have been synthesized by employing the recently developed stereospecific methylation of γ,δ-epoxy acrylates by trimethylaluminum as key steps.