152053-15-1

Basic information

• Product Name: decarestrictine O
• Synonyms: decarestrictine O
• CAS NO: 152053-15-1
• Molecular Formula: C10H16 O5
• Molecular Weight: 216.23
• Mol File: 152053-15-1.mol

Chemical Properties

• Boiling Point: 442.7°Cat760mmHg
• Flash Point: 176.2°C
• Appearance: /
• Density: 1.278g/cm³
• Vapor Pressure: 1.07E-09mmHg at 25°C
• Refractive Index: 1.53
• CAS DataBase Reference: decarestrictine O(CAS DataBase Reference)
• NIST Chemistry Reference: decarestrictine O(152053-15-1)
• EPA Substance Registry System: decarestrictine O(152053-15-1)

Safety Data

• Hazardous Substances Data: 152053-15-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H16O5/c1-6-4-9(13)8(12)3-2-7(11)5-10(14)15-6/h2-3,6-9,11-13H,4-5H2,1H3/b3-2-/t6-,7-,8+,9+/m1/s1

Upstream product

• 1240380-64-6 C₂₁H₂₈O₆ 
• 1300690-07-6 (E)-ethyl 3-[(4S,5S)-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate 
• 140836-86-8 ethyl 3-((4S,5S)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)propanoate 
• 140923-71-3 ethyl 3-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)propanoate 
• 608532-25-8 3-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)propan-1-ol 
• 1408169-88-9 (S)-3-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxan-4-yl)propane-1,2-diol 
• 1408169-89-0 (S)-3-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-hydroxypropyl4-methyl benzenesulfonate 
• 1240380-51-1 (R)-1-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-propan-2-ol 
• 1408169-96-9 (R)-1-[(4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]propan-2-yl (S)-3-[(tert-butyldimethylsilyl)oxy]pent-4-enoate 
• 1408169-97-0 (3S,5R,9S,11S,E)-9-(tert-butyldimethylsilyloxy)-2,2,5-trimethyl-4,5,8,9-tetrahydro-3-[1,3]dioxolo[4,5]oxecin-7-one 
• 124575-40-2 ethyl 3-((4S,5R)-5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl)propanoate 
• 140923-73-5 3-((4S,5S)-2,2-Dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-propionaldehyde 
• 562823-71-6 2-((4S,5S)-5-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol 
• 1566591-26-1 (2-(4S,5S)-5-((benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethoxy)(tert-butyl)dimethylsilane 

Relevant articles and documents

Synthesis of Ophiocerins A, B and C, Botryolide E, Decarestrictine O, Stagonolide C and 9-epi-Stagonolide C Employing Chiral Hexane-1,2,3,5-tetraol Derivatives as Building Blocks

An organocatalytic approach to the synthesis of (2R,3S)-hexane-1,2,3,5-tetraol (11) derivatives (in the forms of different stereoisomers and bearing different protecting groups) has been developed. The key chiral intermediates 11 were prepared with complete stereocontrol through the proline-catalyzed intermolecular aldol reaction between acetone and d-glyceraldehyde acetonide. The synthetic utility of the intermediates was demonstrated by their transformation into the title hydroxylated pyrans and a variety of unsaturated lactones through standard synthetic protocols.

A facile chiral pool synthesis of 9-epi-decarestrictine-D, decarestrictine-D and O

A facile chiral pool total synthesis of 9-epi-decarestrictine-D, decarestrictine-D and O has been achieved from l-(+)-diethyl tartrate. The strategy utilized is conventional and flexible. Wittig homologation and Grubbs ring closing metathesis are the key reactions employed for the synthesis of the title molecules.

Stereoselective total synthesis of decarestrictine O

The stereoselective total synthesis of decarestrictine O, a polyketide natural product is described. The synthesis involves MacMillan α-hydroxylation, C1-Wittig olefination, hydrolytic kinetic resolution and ring closing metathesis (RCM) as key steps. Improved efficiency was achieved by using the DIBAL mediated reductive transformation of trans-dimethyl l-tartrate acetonide into -hydroxy α,β-unsaturated ester in a single step.

First stereoselective total synthesis of decarestrictine O via RCM protocol

A convergent first stereoselective total synthesis of decarestrictine O via RCM protocol starting from 1,3-propanediol and propylene oxide is reported.