2-(7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl)cyclopentane-1-carboxylic acid

Base Information

Chemical Name:2-(7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl)cyclopentane-1-carboxylic acid
CAS No.:97328-74-0
Molecular Formula:C₂₈H₄₃NO₆
Molecular Weight:489.653
Hs Code.:
European Community (EC) Number:811-923-0
DSSTox Substance ID:DTXSID40913983
Wikipedia:Borrelidin
Mol file:97328-74-0.mol

Synonyms:borrelidin;treponemycin

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Chemical Property of 2-(7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl)cyclopentane-1-carboxylic acid

Chemical Property:

Vapor Pressure:2.6E-23mmHg at 25°C
XLogP3:5.6
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:2
Exact Mass:489.30903809
Heavy Atom Count:35
Complexity:827

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC1CC(CC(C(C(=CC=CCC(OC(=O)CC(C(C1)C)O)C2CCCC2C(=O)O)C#N)O)C)C
Isomeric SMILES:C[C@H]1C[C@H](C[C@@H]([C@H](C(=CC=CC[C@H](OC(=O)C[C@@H]([C@H](C1)C)O)[C@@H]2CCC[C@H]2C(=O)O)C#N)O)C)C

Technology Process of 2-(7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl)cyclopentane-1-carboxylic acid

There total 180 articles about 2-(7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl)cyclopentane-1-carboxylic acid 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: 94.0%

: 631919-63-6
(1'R,1S,2S,2'R,8R,9S,11R,13S,15S,16S)-2-(7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-oxacyclooctadeca-4,6-dien-2-yl)-cyclopentane-1'-carboxylic acid 2-trimethylsilanyl-ethyl ester

: 7184-60-3,97328-74-0
borrelidin

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 2h;
DOI:10.1021/ja030139k

Reference yield:

: 57287-24-8
(1R,2R)-1,2-(dihydroxymethyl)cyclopentane

: 7184-60-3,97328-74-0
borrelidin

Guidance literature:: Multi-step reaction with 26 steps

1.1: NaH / dimethylformamide / -20 - 20 °C

2.1: 6.24 g / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

3.1: 54 percent / tetrahydrofuran / 0.5 h / -78 °C

4.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

5.1: H₂O; NMO; OsO₄ / acetone / 4 h / 20 °C

6.1: 533 mg / NaIO₄; H₂O / methanol / 2 h / 0 °C

7.1: 73 percent / benzene / 48 h / 80 °C

8.1: 84 percent / benzene / 39 h / 70 °C

9.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C

10.1: 452 mg / Et₃N; DMAP / benzene / 2 h / 20 °C

11.1: 96 percent / PPTS / ethanol / 16 h / 50 °C

12.1: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.5 h / 20 °C

13.1: SmI₂ / tetrahydrofuran / 1 h / -78 °C

13.2: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

14.1: DMAP / pentane / 168 h / 20 °C

14.2: 31.2 mg / NaBH₄; CeCl₃*7H₂O / methanol / 0.5 h / 0 °C

15.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

16.1: 85 percent / NaBH₄ / Pd(PPh₃)4 / methanol / 0.5 h / 0 °C

17.1: 69 percent / NH₃; Et₃N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C

18.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH₂Cl₂ / 1.5 h / 20 °C

19.1: 73 percent / K₂CO₃; MeOH / 1.5 h / 20 °C

20.1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

21.1: 8.50 mg / NaBH₄; CeCl₃*7H₂O / methanol / 0.08 h / 0 °C

22.1: 75 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

23.1: 90 percent / DDQ; H₂O / CH₂Cl₂ / 0.25 h / 0 °C

24.1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

25.1: NaClO₂; NaH₂PO₄*2H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 0.5 h / 20 °C

26.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C

With pyridine; 2,6-dimethylpyridine; methanol; dmap; sodium chlorite; sodium tetrahydroborate; sodium periodate; sodium dihydrogenphosphate; osmium(VIII) oxide; N-methyl-2-indolinone; samarium diiodide; cerium(III) chloride; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 4 A molecular sieve; ammonia; water; pyridinium p-toluenesulfonate; 2-chloro-1,3-dimethylimidazolinium chloride; sodium hydride; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; pentane; benzene; 2.1: Dess-Martin oxidation / 7.1: Wittig reaction / 8.1: Wittig reaction / 13.2: Dess-Martin oxidation / 20.1: Dess-Martin oxidation / 24.1: Dess-Martin oxidation;
DOI:10.1021/jo062089i

Reference yield:

: 90270-02-3,97937-36-5
(2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate

: 7184-60-3,97328-74-0
borrelidin

Guidance literature:: Multi-step reaction with 34 steps

1.1: 98 percent / imidazole / CH₂Cl₂ / 0.5 h / 20 °C

2.1: 98 percent / K₂CO₃; MeOH / 2 h / 20 °C

3.1: imidazole / dimethylformamide / 0 - 20 °C

4.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C

5.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH₂Cl₂ / 0.5 h / 20 °C

6.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C

6.2: tetrahydrofuran; hexane / 1 h / -30 °C

6.3: tetrahydrofuran; hexane / -20 °C

7.1: 2.44 g / Bu₃P; HCO₂NH₄ / Pd(PPh₃)4 / toluene / 1 h / 70 °C

8.1: 97 percent / DDQ; H₂O / CH₂Cl₂ / 0.5 h / 20 °C

9.1: 80 percent / TiCl₄ / CH₂Cl₂; hexane / 0.25 h / -15 °C

10.1: 91 percent / H₂ / Rh[(nbd)dppb]BF₄ / CH₂Cl₂ / 2 h / 20 °C / 7500.75 Torr

11.1: 100 percent / PPTS / CH₂Cl₂ / 2 h / 20 °C

12.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

13.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH₂Cl₂ / 0.5 h / 20 °C

14.1: 92 percent / SmI₂ / tetrahydrofuran / 0.33 h / -78 °C

15.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

16.1: 347 mg / LiOH; aq. H₂O₂ / tetrahydrofuran / 3 h / 0 °C

17.1: Et₃N / benzene / 1 h / 20 °C

18.1: 452 mg / Et₃N; DMAP / benzene / 2 h / 20 °C

19.1: 96 percent / PPTS / ethanol / 16 h / 50 °C

20.1: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.5 h / 20 °C

21.1: SmI₂ / tetrahydrofuran / 1 h / -78 °C

21.2: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

22.1: DMAP / pentane / 168 h / 20 °C

22.2: 31.2 mg / NaBH₄; CeCl₃*7H₂O / methanol / 0.5 h / 0 °C

23.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

24.1: 85 percent / NaBH₄ / Pd(PPh₃)4 / methanol / 0.5 h / 0 °C

25.1: 69 percent / NH₃; Et₃N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C

26.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH₂Cl₂ / 1.5 h / 20 °C

27.1: 73 percent / K₂CO₃; MeOH / 1.5 h / 20 °C

28.1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

29.1: 8.50 mg / NaBH₄; CeCl₃*7H₂O / methanol / 0.08 h / 0 °C

30.1: 75 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

31.1: 90 percent / DDQ; H₂O / CH₂Cl₂ / 0.25 h / 0 °C

32.1: Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

33.1: NaClO₂; NaH₂PO₄*2H₂O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 0.5 h / 20 °C

34.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; methanol; dmap; lithium hydroxide; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; n-butyllithium; N-methyl-2-indolinone; samarium diiodide; cerium(III) chloride; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; ethanol; tributylphosphine; 4 A molecular sieve; tetrabutyl ammonium fluoride; ammonia; water; hydrogen; dihydrogen peroxide; ammonium formate; pyridinium p-toluenesulfonate; titanium tetrachloride; 2-chloro-1,3-dimethylimidazolinium chloride; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF₄; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; pentane; benzene; 21.2: Dess-Martin oxidation / 28.1: Dess-Martin oxidation / 32.1: Dess-Martin oxidation;
DOI:10.1021/jo062089i