87758-52-9

Basic information

• Product Name: (2S)-Tetrahydro-3β,5β-dimethyl-2α-[(1R,3R,5E)-1,3,5-trimethyl-2-oxo-5-octenyl]-6-[(1S)-1-methyl-2-oxobutyl]-2H-pyran-2β,4β-diol
• Synonyms: (2S)-Tetrahydro-3β,5β-dimethyl-2α-[(1R,3R,5E)-1,3,5-trimethyl-2-oxo-5-octenyl]-6-[(1S)-1-methyl-2-oxobutyl]-2H-pyran-2β,4β-diol;Denticulatin B
• CAS NO: 87758-52-9
• Molecular Formula: C23H40O5
• Molecular Weight: 396.5607
• Mol File: 87758-52-9.mol

Chemical Properties

• Boiling Point: 531.5°Cat760mmHg
• Flash Point: 171.7°C
• Appearance: /
• Density: 1.024g/cm³
• Vapor Pressure: 1.62E-13mmHg at 25°C
• Refractive Index: 1.485
• CAS DataBase Reference: (2S)-Tetrahydro-3β,5β-dimethyl-2α-[(1R,3R,5E)-1,3,5-trimethyl-2-oxo-5-octenyl]-6-[(1S)-1-methyl-2-oxobutyl]-2H-pyran-2β,4β-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-Tetrahydro-3β,5β-dimethyl-2α-[(1R,3R,5E)-1,3,5-trimethyl-2-oxo-5-octenyl]-6-[(1S)-1-methyl-2-oxobutyl]-2H-pyran-2β,4β-diol(87758-52-9)
• EPA Substance Registry System: (2S)-Tetrahydro-3β,5β-dimethyl-2α-[(1R,3R,5E)-1,3,5-trimethyl-2-oxo-5-octenyl]-6-[(1S)-1-methyl-2-oxobutyl]-2H-pyran-2β,4β-diol(87758-52-9)

Safety Data

• Hazardous Substances Data: 87758-52-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C23H40O5/c1-9-11-13(3)12-14(4)20(25)17(7)23(27)18(8)21(26)16(6)22(28-23)15(5)19(24)10-2/h11,14-18,21-22,26-27H,9-10,12H2,1-8H3/b13-11+/t14-,15-,16-,17+,18+,21+,22?,23-/m1/s1

Upstream product

• 140925-37-7 (E)-(2S,4S,6R)-2-[(4S,5S,6R)-2,2-Di-tert-butyl-5-methyl-6-((S)-1-methyl-2-oxo-butyl)-[1,3,2]dioxasilinan-4-yl]-4,6,8-trimethyl-undec-8-ene-3,5-dione 
• 140870-63-9 (E)-(2S,4R,6R)-2-[(4S,5S,6R)-2,2-Di-tert-butyl-5-methyl-6-((S)-1-methyl-2-oxo-butyl)-[1,3,2]dioxasilinan-4-yl]-4,6,8-trimethyl-undec-8-ene-3,5-dione 
• 126615-48-3 6(R)-<1(S)-Methyl-2-oxobutyl>-4(S)-<1(S),3(RS),5(R),7-tetramethyl-2,4-dioxo-7(E)-decenyl>-2(S),5(S)-dimethyl-2-(p-methoxyphenyl)-1,3-dioxane 
• 135503-16-1 (2S,3S,4R,5S,6R)-2-Ethyl-4-(p-methoxybenzyloxy)-3,5-dimethyl-6-<(1R)-1-methyl-2-propenyl>-tetrahydro-2H-pyran-2-ol 
• 119003-94-0 (3R,4R,5S,6S)-6-(tert-Butyldimethylsilyloxy)-3,5-dimethyl-1-octen-4-ol 
• 119003-95-1 (3R,4R,5S,6S)-6-(tert-Butyldimethylsilyloxy)-4-(p-methoxybenzyloxy)-3,5-dimethyl-1-octene 
• 132565-99-2 (2S)-2-<(2S,3S,4R,5S,6S)-6-Ethyl-6-hydroxy-4-(p-methoxybenzyloxy)-3,5-dimethyl-tetrahydro-2H-pyran-2-yl>propanal 
• 132565-96-9 (2S,3R,4S)-3-(p-Methoxybenzyloxy)-2,4-dimethyl-5-oxoheptanal 
• 87758-53-0 (E)-(4R)-4,6-dimethyl-non-6-en-3-one 
• 132566-03-1 (2S,4S,6R,8E)-2-<(2S,3S,4R,5S,6S)-6-Ethyl-6-hydroxy-4-(p-methoxybenzyloxy)-3,5-dimethyl-tetrahydro-2H-pyran-2-yl>-4,6,8-trimethyl-8-undecen-3,5-dione 
• 132566-01-9 (2R,3S,4R,6R,8E)-2-<(2S,3S,4R,5S,6S)-6-Ethyl-6-hydroxy-4-(p-methoxybenzyloxy)-3,5-dimethyl-tetrahydro-2H-pyran-2-yl>-3-hydroxy-4,6,8-trimethyl-8-undecen-5-one 
• 132565-98-1 (2S,3S,4R,5S,6R)-2-Ethyl-4-(p-methoxybenzyloxy)-6-<(1R,2Z)-3-methoxy-1-methyl-2-propenyl>-3,5-dimethyl-tetrahydro-2H-pyran-2-ol 
• 135393-94-1 (3S,4R,5R,6R)-5-(p-Methoxybenzyloxy)-4,6-dimethyl-7-octen-3-ol 
• 135393-95-2 (4S,5R,6R)-5-(p-Methoxybenzyloxy)-4,6-dimethyl-7-octen-3-one 

Downstream Products

• 87697-98-1 Denticulatin A 

Relevant articles and documents

Enantioselective total synthesis of (-)-denticulatins A and B using a novel group-selective aldolization of a meso dialdehyde as a key step

The diastereoselective synthesis of (-)-denticulatin A (1a) was achieved for the first time in 9 steps (41% yield) based on a novel group-selective aldolization of a meso dialdehyde as a key step. The inherent chirality present in bornanesultam 4 was thus transmitted to the five stereocenters spanning C4-C8 in key intermediate 8. In addition, denticulatin B (1b) was obtained from the common intermediate 8 en route to denticulatin A in 10 steps and 35% overall yield.

Asymmetric Synthesis of (-)-Denticulatins A and B via Group-Selective Aldolization of a Meso Dialdehyde with a Chiral N-Propionylsultam.

Aldolization of meso dialdehyde 3 with a borylenolate obtained from chiral propionylsultam 4 yields efficiently lactols 5 with simultaneous generation of five stereogenic centers.Dithioketalization/O-desilylation of 5 affords acyclic diol 9 which is conve

Studies in Polypropionate Synthesis: Stereoselective Synthesis of (-)-Denticulatins A and B.

(-)-Denticulatin B (2) was prepared in 9 steps (20percent yield) with 70percent overall ds starting from the ethyl ketone (R)-8.Key steps are the novel boron-mediated aldol/reduction, 8 -> 12, the titanium aldol coupling, 6 + 5 -> 18, and the HF-pyridine cyclisation, 20 -> 2.Epimerisation at C10 in 20 led to (-)-denticulatin A (1).

Stereoselective Synthesis of Alcohols, XXXVIII. - Stereoselective Total Synthesis of the Denticulatins

The total synthesis of the denticulatins 1 is described.Key feature is the efficient generation of the C-1-to-C-9 building block 37 by three consecutive stereoselective carbon-carbon bond-forming steps using chiral allylboronates.The C10-to-C-17 building block was obtained by kinetic Sharpless resolution of an allylic alcohol followed by an Ireland-Claisen rearrangement. Key Words: Marine natural products / Hemiketal formation, selective / Denticulatins

Total Synthesis of (-)-Denticulatins A and B: Marine Polypropionates from Siphonaria denticulata

A synthesis of the marine polypropionates (-)-denticulatin A (2a) and B (2b) is described.The targets, which are β-hydroxy ketones wherein the hydroxyl group is also a tertiary hemiketal, are sensitive to acid dehydration.An open chain form (26) of the de