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Technology Process of 5-(1-Hydroxytridecyl)oxolan-2-one

5-(1-Hydroxytridecyl)oxolan-2-one

Base Information
  • Chemical Name:5-(1-Hydroxytridecyl)oxolan-2-one
  • CAS No.:134698-86-5
  • Molecular Formula:C17H32 O3
  • Molecular Weight:284.439
  • Hs Code.:
  • Wikidata:Q105285428
  • Metabolomics Workbench ID:48305
  • Mol file:134698-86-5.mol
5-(1-Hydroxytridecyl)oxolan-2-one

Synonyms:5-(1-hydroxytridecyl)oxolan-2-one;(5R)-5-[(1R)-1-hydroxytridecyl]oxolan-2-one;LMFA05000682

Suppliers and Price of 5-(1-Hydroxytridecyl)oxolan-2-one
Supply Marketing:
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
Total 4 raw suppliers
Chemical Property of 5-(1-Hydroxytridecyl)oxolan-2-one
Chemical Property:
  • Vapor Pressure:4.42E-09mmHg at 25°C 
  • Boiling Point:427°C at 760 mmHg 
  • Flash Point:169.3°C 
  • PSA：46.53000 
  • Density:0.977g/cm3 
  • LogP:4.36390 
  • XLogP3:5.8
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:3
  • Rotatable Bond Count:12
  • Exact Mass:284.23514488
  • Heavy Atom Count:20
  • Complexity:253
Purity/Quality:

98%min *data from raw suppliers

Safty Information:
  • Pictogram(s):  
  • Hazard Codes: 
MSDS Files:

SDS file from LookChem

Useful:
  • Canonical SMILES:CCCCCCCCCCCCC(C1CCC(=O)O1)O
Technology Process of 5-(1-Hydroxytridecyl)oxolan-2-one

There total 1 articles about 5-(1-Hydroxytridecyl)oxolan-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

1-hydroxy-2(E)-pentadecene
6064-48-8

1-hydroxy-2(E)-pentadecene

(-)-(4R,5R)-muricatacin
134698-86-5

(-)-(4R,5R)-muricatacin

Guidance literature:
Multi-step reaction with 4 steps
1: 98 percent / MnO2 / hexane / 24 h / 20 °C
2: 93 percent / 18-crown-6; t-BuOK / tetrahydrofuran / 2.5 h / -78 °C
3: 86 percent / OsO4; MeSO2NH2; (DHQD)2PHAL / K3Fe(CN)6; K2CO3 / 2-methyl-propan-2-ol; H2O / 0 °C
4: 98 percent / H2 / Pd/C / methanol / 24 h / 760 Torr
With manganese(IV) oxide; osmium(VIII) oxide; 18-crown-6 ether; methanesulfonamide; potassium tert-butylate; hydrogen; 1,4-bis(9-O-dihydroquinidine)phthalazine; palladium on activated charcoal; potassium carbonate; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; hexane; water; tert-butyl alcohol; 2: Still-Gennari reaction / 3: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo061057s

Reference yield: 90.0%

(-)-(4R,5R)-muricatacin
134698-86-5

(-)-(4R,5R)-muricatacin

benzoyl chloride
98-88-4

benzoyl chloride

(R)-1-((R)-5-oxotetrahydrofuran-2-yl)tridecyl benzoate

(R)-1-((R)-5-oxotetrahydrofuran-2-yl)tridecyl benzoate

Guidance literature:
With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1055/s-0036-1590858

Reference yield:

(-)-(4R,5R)-muricatacin
134698-86-5

(-)-(4R,5R)-muricatacin

(S)-3-(12-{(2S,3R)-3-[2-((2S,3R)-3-Dodecyl-oxiranyl)-ethyl]-oxiranyl}-dodecyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

(S)-3-(12-{(2S,3R)-3-[2-((2S,3R)-3-Dodecyl-oxiranyl)-ethyl]-oxiranyl}-dodecyl)-5-methyl-3-phenylsulfanyl-dihydro-furan-2-one

Guidance literature:
Multi-step reaction with 19 steps
1: i-Pr2NEt / CH2Cl2
2: DIBAL / CH2Cl2
3: 76 percent / NaH / tetrahydrofuran / -78 °C
4: PPTS / CH2Cl2
5: AD-mix α, CH3SO2NH2 / 2-methyl-propan-2-ol; H2O
6: PPTS / CH2Cl2
7: LiAlH4 / diethyl ether
8: pyridine
9: PPTS / methanol
10: KOH
11: 98 percent / PPTS / CH2Cl2
12: 96 percent / BF3*Et2O / tetrahydrofuran
13: i-Pr2NEt / CH2Cl2
14: PPTS / methanol
15: 53 percent / CuI, pyrrolidine / Pd(Ph3P)4
16: 77 percent / H2 / Rh(Ph3P)3Cl / benzene
17: Et3N / CH2Cl2
18: HCl / methanol
19: KOH / tetrahydrofuran
With pyrrolidine; pyridine; hydrogenchloride; potassium hydroxide; AD-mix-α; copper(l) iodide; lithium aluminium tetrahydride; methanesulfonamide; boron trifluoride diethyl etherate; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; Wilkinson's catalyst; tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; tert-butyl alcohol; benzene;
DOI:10.1016/0040-4039(96)01086-6
upstream raw materials:

1-hydroxy-2(E)-pentadecene

Downstream raw materials:

(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-1-((R)-5-oxo-tetrahydro-furan-2-yl)-tridecyl ester

(4R,5R)-4-Hydroxy-5-methoxymethoxy-heptadecanoic acid benzylamide

Methanesulfonic acid (1S,4R,5R)-4-methanesulfonyloxy-5-methoxymethoxy-1-[(S)-1-methoxymethoxy-13-((S)-5-methyl-2-oxo-3-phenylsulfanyl-tetrahydro-furan-3-yl)-tridecyl]-heptadecyl ester

(2S,5R,1'S, 1''R)-2-(1'-benzyloxypent-4'-ynyl)-5-(2'',4''-dioxaheptadecan-5''-yl)tetrahydrofuran

Refernces

Total synthesis of (+)-4-deoxygigantecin

10.1016/S0040-4039(97)00856-3

The study reports the first total synthesis of the natural product (+)-4-deoxygigantecin (1), a non-adjacent bis-tetrahydrofuran type annonaceous acetogenin. The synthesis began with enantiomerically pure (-)-muricatacin (3), which was converted through a series of reactions into key intermediate 5. This intermediate was then transformed into the final product via the formation of a bis-tetrahydrofuran unit 11 and a coupling reaction with iodo lactone synthon 16. The study highlights the use of various reagents and conditions, such as MOM ether for protection, n-BuLi for alkylation, Na in liquid ammonia for reduction, and the Sharpless asymmetric dihydroxylation for selective hydroxylation. The final product was obtained in 95% overall yield and its properties were consistent with those of the natural compound, demonstrating the successful synthesis of a complex natural product with significant biological activities.

Stereoselective synthesis of (5S,6S)- and (5S,6R)-aza-muricatacin from an L-glutamic acid derivative

10.1016/S0957-4166(01)00251-8

Muricatacin is a bioactive hydroxy lactone compound that is isolated from the plant Annona muricata. It is mentioned in the research as a compound with physiological activity. The study focuses on the synthesis of aza-muricatacin, a non-natural aza-analogue of muricatacin, which also exhibits interesting cytotoxic activity. The research aims to synthesize different diastereoisomers of aza-muricatacin, specifically the (5S,6S)- and (5S,6R)-isomers, starting from a common precursor derived from L-glutamic acid.

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