127393-89-9

Basic information

• Product Name: decarestrictine D
• Synonyms: decarestrictine D;Decarestrictin D;SM 133;Tuckolide
• CAS NO: 127393-89-9
• Molecular Formula: C₁₀H₁₆O₅
• Molecular Weight: 216.231
• Mol File: 127393-89-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 121-123℃ (dichloromethane hexane )
• Boiling Point: 442.7°C at 760 mmHg
• Flash Point: 176.2°C
• Appearance: /
• Density: 1.278g/cm³
• Vapor Pressure: 1.07E-09mmHg at 25°C
• Refractive Index: 1.53
• PKA: 13.34±0.70(Predicted)
• CAS DataBase Reference: decarestrictine D(CAS DataBase Reference)
• NIST Chemistry Reference: decarestrictine D(127393-89-9)
• EPA Substance Registry System: decarestrictine D(127393-89-9)

Safety Data

• Hazardous Substances Data: 127393-89-9(Hazardous Substances Data)

Usage

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

Upstream product

• 603040-81-9 (R)-1-methoxy-4-((pent-4-yn-2-yloxy)methyl)benzene 
• 851278-43-8 (1'E,4'R)-2-[4'-(4-methoxybenzyloxy)-1'-pentenyl]-5,5-dimethyl-1,3,2-dioxaborinane 
• 851278-44-9 (1Z,3S)-1-bromo-5-[(tert-butyldiphenylsilyl)oxy]-1-penten-3-ol 
• 851278-52-9 methyl (3S,4S,5E,7S,9R)-9-hydroxy-3,4,7-tri[(methoxymethyl)oxy]-5-decenoate 
• 929118-01-4 (E)-(3S,4S,7S,9R)-9-Hydroxy-3,4,7-tris-methoxymethoxy-dec-5-enoic acid 
• 851278-57-4 (1E,3S)-5-[(tert-butyldiphenylsilyl)oxy]-1-trimethylsilyl-1-penten-3-ol 
• 851278-45-0 (1E)-5-[(tert-butyldiphenylsilyl)oxy]-1-trimethylsilyl-1-penten-3-ol 
• 929117-87-3 (3S,4S,5E,7S,9R)-9-[(4-methoxybenzyl)oxy]-3,4,7-tri[(methoxymethyl)oxy]-5-decen-1-ol 
• 851278-51-8 methyl (3S,4S,5E,7S,9R)-9-[(4-methoxybenzyl)oxy]-3,4,7-tri[(methoxymethyl)oxy]-5-decenoate 
• 929118-02-5 (E)-(3S,4S,7S,9R)-9-(4-Methoxy-benzyloxy)-3,4,7-tris-methoxymethoxy-dec-5-enoic acid 
• 851278-40-5 (3S,4Z,6E,9R)-1-[(tert-butyldiphenylsilyl)oxy]-9-[(4-methoxybenzyl)oxy]-4,6-decadien-3-ol 
• 851278-41-6 (3S,4R,5S,6E)-1-(tert-butyldiphenylsilyloxy)-4,5-epoxy-9-(4-methoxybenzyloxy)-6-decen-3-ol 
• 929117-86-2 (E)-(3S,4S,7S,9R)-1-(tert-Butyl-diphenyl-silanyloxy)-9-(4-methoxy-benzyloxy)-dec-5-ene-3,4,7-triol 
• 851278-42-7 (1S,2E,4S,5S,2'R)-7-[(tert-butyldiphenylsilyl)oxy]-4,5-dihydroxy-1-[2'-[(4-methoxybenzyl)oxy]propyl]-2-heptenyl acetate 

Downstream Products

• 212895-08-4 Benzoic acid (2S,3S,5R,6R)-6-((E)-(2R,4S,7S,8S)-7,8-dihydroxy-2-methyl-10-oxo-3,4,7,8,9,10-hexahydro-2H-oxecin-4-yloxy)-5-iodo-2-methyl-tetrahydro-pyran-3-yl ester 
• 212895-20-0 Benzoic acid (2S,3S,5R,6S)-6-((E)-(4S,5S,8S,10R)-5,8-dihydroxy-10-methyl-2-oxo-3,4,5,8,9,10-hexahydro-2H-oxecin-4-yloxy)-5-iodo-2-methyl-tetrahydro-pyran-3-yl ester 

Relevant articles and documents

Total synthesis of (-)-decarestrictine D through a stereoselective intramolecular Nozaki-Hiyama-Kishi reaction

A concise total synthesis of (-)-decarestrictine D (1) from 1,3- propanediol and polyhydroxybutyrate (PHB) is described. The approach involves the stereoselective intramolecular Nozaki-Hiyama-Kishi coupling to construct the decanolide ring and to set the proper configuration at C-7.

An efficient total synthesis of decarestrictine D

An efficient total synthesis of decarestrictine D has been achieved using cross-metathesis or ring-closing metathesis and Yamaguchi macrolactonization as key steps. The stereogenic centres were generated by means of hydrolytic kinetic resolution (HKR) and

Stereoselective total synthesis of (-)-decarestrictine D from l-malic acid

A convergent stereoselective total synthesis of (-)-decarestrictine D from l-malic acid is reported.