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7184-60-3

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Basic Information
CAS No.: 7184-60-3
Name: BORRELIDIN
Article Data: 5
Molecular Structure:
Molecular Structure of 7184-60-3 (BORRELIDIN)
Formula: C28H43NO6
Molecular Weight: 489.653
Synonyms: 2-(7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl)-cyclopentanecar boxylic acid;Treponemycin;NSC 216128;BRN 0066270;AC1O5MFI;B1936_SIGMA;(1R,2R)-2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid;
Density: 1.14 g/cm3
Melting Point: 143-145℃
Boiling Point: 710.3 °C at 760 mmHg
Flash Point: 383.4 °C
Solubility: DMSO: 1 mg/mL
Appearance: White to off-white powder
PSA: 127.85000
LogP: 4.63558
Related products
Synthetic route
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

borrelidin

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 2h;94%

(1R,2R)-2-((4E,6Z)-(2S,8R,9S,11R,13S,15S,16S)-7-Cyano-8,16-bis-methoxymethoxy-9,11,13,15-tetramethyl-18-oxo-oxacyclooctadeca-4,6-dien-2-yl)-cyclopentanecarboxylic acid

7184-60-3

borrelidin

Conditions
ConditionsYield
With dimethylboron bromide In dichloromethane at -78℃; for 1h;
768395-41-1

(1R,2R)-2-((4E,6Z)-(2S,9S,11R,13S,15S,16S)-7-Cyano-16-hydroxy-9,11,13,15-tetramethyl-8,18-dioxo-oxacyclooctadeca-4,6-dien-2-yl)-cyclopentanecarboxylic acid

A

7184-60-3

borrelidin

B

(1R,2R)-2-((4E,6Z)-(2S,8S,9S,11R,13S,15S,16S)-7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-oxacyclooctadeca-4,6-dien-2-yl)-cyclopentanecarboxylic acid

Conditions
ConditionsYield
With sodium tetrahydroborate; cerium(III) chloride In methanol at 0℃; for 1h; Luche reaction; Title compound not separated from byproducts;

(1R,2R)-2-[(4E,6Z)-(2S,8R,9S,11R,13S,15S,16S)-8,16-Bis-(tert-butyl-dimethyl-silanyloxy)-7-cyano-9,11,13,15-tetramethyl-18-oxo-oxacyclooctadeca-4,6-dien-2-yl]-cyclopentanecarboxylic acid

7184-60-3

borrelidin

Conditions
ConditionsYield
With pyridine hydrogenfluoride In tetrahydrofuran at 20℃; for 48h;5.2 mg
With pyridine; pyridine hydrogenfluoride In tetrahydrofuran at 20℃; for 48h;5.20 mg

C36H48SiO3CO2CH2

7184-60-3

borrelidin

Conditions
ConditionsYield
Multi-step reaction with 28 steps
1.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C
2.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C
3.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C
4.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr
5.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C
6.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C
7.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C
8.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C
9.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
10.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C
11.1: Et3N / benzene / 1 h / 20 °C
12.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C
13.1: 96 percent / PPTS / ethanol / 16 h / 50 °C
14.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C
15.1: SmI2 / tetrahydrofuran / 1 h / -78 °C
15.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
16.1: DMAP / pentane / 168 h / 20 °C
16.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C
17.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
18.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C
19.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C
20.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C
21.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C
22.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
23.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C
24.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
25.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C
26.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
27.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C
28.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 27 steps
1.1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C
2.1: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C
3.1: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C
4.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr
5.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C
6.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C
7.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C
8.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C
9.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
10.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C
11.1: Et3N / benzene / 1 h / 20 °C
12.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C
13.1: 96 percent / PPTS / ethanol / 16 h / 50 °C
14.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C
15.1: SmI2 / tetrahydrofuran / 1 h / -78 °C
15.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
16.1: DMAP / pentane / 168 h / 20 °C
16.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C
17.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
18.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C
19.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C
20.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C
21.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
22.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C
23.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
24.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C
25.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
26.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C
27.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 20 steps
1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C
2: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C
3: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C
4: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr
5: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C
6: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C
7: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C
8: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C
9: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
10: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C
11: Et3N / benzene / 1 h / 20 °C
12: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C
13: 93 percent / PPTS / ethanol / 10 h / 50 °C
14: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C
15: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C
16: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
17: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C
18: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
19: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C
20: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 22 steps
1: 2.44 g / Bu3P; HCO2NH4 / Pd(PPh3)4 / toluene / 1 h / 70 °C
2: 97 percent / DDQ; H2O / CH2Cl2 / 0.5 h / 20 °C
3: 80 percent / TiCl4 / CH2Cl2; hexane / 0.25 h / -15 °C
4: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr
5: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C
6: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C
7: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C
8: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C
9: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
10: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C
11: Et3N / benzene / 1 h / 20 °C
12: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C
13: 93 percent / PPTS / ethanol / 10 h / 50 °C
14: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C
15: 19 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C
16: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
17: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C
18: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
19: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C
20: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
21: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C
22: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
714973-96-3

(2S,4R,8S,Z)-9-(tert-butyldiphenylsilyloxy)-2,4,6,8-tetramethylnon-3-en-1-ol

7184-60-3

borrelidin

Conditions
ConditionsYield
Multi-step reaction with 25 steps
1.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr
2.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C
3.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C
4.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C
5.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C
6.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
7.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C
8.1: Et3N / benzene / 1 h / 20 °C
9.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C
10.1: 96 percent / PPTS / ethanol / 16 h / 50 °C
11.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C
12.1: SmI2 / tetrahydrofuran / 1 h / -78 °C
12.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
13.1: DMAP / pentane / 168 h / 20 °C
13.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C
14.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
15.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C
16.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C
17.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C
18.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C
19.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
20.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C
21.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
22.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C
23.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
24.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C
25.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 24 steps
1.1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr
2.1: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C
3.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C
4.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C
5.1: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C
6.1: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
7.1: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C
8.1: Et3N / benzene / 1 h / 20 °C
9.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C
10.1: 96 percent / PPTS / ethanol / 16 h / 50 °C
11.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C
12.1: SmI2 / tetrahydrofuran / 1 h / -78 °C
12.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
13.1: DMAP / pentane / 168 h / 20 °C
13.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C
14.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
15.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C
16.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C
17.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C
18.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
19.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C
20.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
21.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C
22.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
23.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C
24.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 17 steps
1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr
2: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C
3: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C
4: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C
5: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C
6: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
7: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C
8: Et3N / benzene / 1 h / 20 °C
9: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C
10: 93 percent / PPTS / ethanol / 10 h / 50 °C
11: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C
12: 21 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C
13: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
14: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C
15: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
16: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C
17: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 19 steps
1: 91 percent / H2 / Rh[(nbd)dppb]BF4 / CH2Cl2 / 2 h / 20 °C / 7500.75 Torr
2: 100 percent / PPTS / CH2Cl2 / 2 h / 20 °C
3: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C
4: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C
5: 92 percent / SmI2 / tetrahydrofuran / 0.33 h / -78 °C
6: 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
7: 347 mg / LiOH; aq. H2O2 / tetrahydrofuran / 3 h / 0 °C
8: Et3N / benzene / 1 h / 20 °C
9: 204 mg / Et3N; DMAP / benzene / 0.5 h / 20 °C
10: 93 percent / PPTS / ethanol / 10 h / 50 °C
11: 79 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH2Cl2 / 0.5 h / 20 °C
12: 19 percent / SmI2; HMPA; O2 / tetrahydrofuran / 1 h / -78 °C
13: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
14: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C
15: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
16: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C
17: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
18: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C
19: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
935872-55-2

C42H66O6SiNCOCF3

7184-60-3

borrelidin

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C
2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
3: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C
4: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
5: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C
6: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
7: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C
8: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
935872-03-0

(3S,4S,6S,8R,10S)-((S,3E,5Z)-7-allyloxy-6-bromo-1-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}-7-oxohepta-3,5-dienyl) 3-(tert-butyldimethylsilyloxy)-4,6,8,10-tetramethyl-11-oxoundecanoate

7184-60-3

borrelidin

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1.1: SmI2 / tetrahydrofuran / 1 h / -78 °C
1.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
2.1: DMAP / pentane / 168 h / 20 °C
2.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C
3.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
4.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C
5.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C
6.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C
7.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C
8.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
9.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C
10.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
11.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C
12.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
13.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C
14.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 13 steps
1.1: SmI2 / tetrahydrofuran / 1 h / -78 °C
1.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
2.1: DMAP / pentane / 168 h / 20 °C
2.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C
3.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
4.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C
5.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C
6.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C
7.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
8.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C
9.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
10.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C
11.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
12.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C
13.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
935872-04-1

(S,2Z,4E)-allyl 2-bromo-7-(tert-butyldimethylsilyloxy)-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienoate

7184-60-3

borrelidin

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C
2.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C
3.1: 96 percent / PPTS / ethanol / 16 h / 50 °C
4.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C
5.1: SmI2 / tetrahydrofuran / 1 h / -78 °C
5.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
6.1: DMAP / pentane / 168 h / 20 °C
6.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C
7.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
8.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C
9.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C
10.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C
11.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C
12.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
13.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C
14.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
15.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C
16.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
17.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C
18.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 17 steps
1.1: 96 percent / HF*pyridine; pyridine / tetrahydrofuran / 228 h / 20 °C
2.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C
3.1: 96 percent / PPTS / ethanol / 16 h / 50 °C
4.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C
5.1: SmI2 / tetrahydrofuran / 1 h / -78 °C
5.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
6.1: DMAP / pentane / 168 h / 20 °C
6.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C
7.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
8.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C
9.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C
10.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C
11.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
12.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C
13.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
14.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C
15.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
16.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C
17.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
935872-05-2

(S,2Z,4E)-allyl 2-bromo-7-hydroxy-7-{(1R,2R)-2-[(4-methoxybenzyloxy)methyl]cyclopentyl}hepta-2,4-dienoate

7184-60-3

borrelidin

Conditions
ConditionsYield
Multi-step reaction with 17 steps
1.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C
2.1: 96 percent / PPTS / ethanol / 16 h / 50 °C
3.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C
4.1: SmI2 / tetrahydrofuran / 1 h / -78 °C
4.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
5.1: DMAP / pentane / 168 h / 20 °C
5.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C
6.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
7.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C
8.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C
9.1: 31 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C
10.1: 73 percent / K2CO3; MeOH / 1.5 h / 20 °C
11.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
12.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C
13.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
14.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C
15.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
16.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C
17.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
Multi-step reaction with 16 steps
1.1: 452 mg / Et3N; DMAP / benzene / 2 h / 20 °C
2.1: 96 percent / PPTS / ethanol / 16 h / 50 °C
3.1: TPAP; NMO; 4 Angstroem molecular sieves / CH2Cl2 / 1.5 h / 20 °C
4.1: SmI2 / tetrahydrofuran / 1 h / -78 °C
4.2: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
5.1: DMAP / pentane / 168 h / 20 °C
5.2: 31.2 mg / NaBH4; CeCl3*7H2O / methanol / 0.5 h / 0 °C
6.1: 85 percent / 2,6-lutidine / CH2Cl2 / 0.5 h / 0 °C
7.1: 85 percent / NaBH4 / Pd(PPh3)4 / methanol / 0.5 h / 0 °C
8.1: 69 percent / NH3; Et3N; BOP / dioxane; tetrahydrofuran / 48 h / 23 °C
9.1: 10 percent / 2-chloro-1,3-dimethylimidazolinium chloride / CH2Cl2 / 1.5 h / 20 °C
10.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
11.1: 8.50 mg / NaBH4; CeCl3*7H2O / methanol / 0.08 h / 0 °C
12.1: 75 percent / 2,6-lutidine / CH2Cl2 / 1 h / 0 °C
13.1: 90 percent / DDQ; H2O / CH2Cl2 / 0.25 h / 0 °C
14.1: Dess-Martin periodinane / CH2Cl2 / 0.5 h / 20 °C
15.1: NaClO2; NaH2PO4*2H2O; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 0.5 h / 20 °C
16.1: 5.20 mg / HF*pyridine; pyridine / tetrahydrofuran / 48 h / 20 °C
View Scheme
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  • 7184-60-3

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    7184-60-3

    7184-60-3

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    Supply top quality products with a reasonable price Application:api

    Hebei Ruishun Trade Co.,Ltd registered capital one million, we have a production of pharmaceutical raw materials, pharmaceutical raw materials factory reagent r&d center, we do

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  • Borrelidin

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    7184-60-3

    Borrelidin

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    BORRELIDIN

    Cfm Oskar Tropitzsch e.K. has been existing in its current version for almost fifteen years now. The beginnings, however, go back more than 200 years to the roots of chemical indus

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  • Borrelidin

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    7184-60-3

    Borrelidin

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    High purity Application:Screening the references, analyzing the expectant ingredients

    Novachemistry offers a broad range of specialty chemicals and customized synthesis services to a range of pharmaceutical, agrochemical and biochemical industries. Novachemistry has

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Specification

The Borrelidin with CAS registry number of 7184-60-3 is also known as 2-(7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl)-cyclopentanecar boxylic acid. The IUPAC name is (1R,2R)-2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl]cyclopentane-1-carboxylic acid. In addition, the formula is C28H43NO6 and the molecular weight is 489.64. This chemical is a white to off-white powder and should be sealed in ventilated and dry place at the temperature of -20 °C.

Physical properties about Borrelidin are: (1)ACD/LogP: 4.31; (2)ACD/LogD (pH 5.5): 3.32; (3)ACD/LogD (pH 7.4): 1.52; (4)ACD/BCF (pH 5.5): 114.07; (5)ACD/BCF (pH 7.4): 1.79; (6)ACD/KOC (pH 5.5): 541.24; (7)ACD/KOC (pH 7.4): 8.51; (8)#H bond acceptors: 7; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction: 1.538; (12)Molar Refractivity: 133.52 cm3; (13)Molar Volume: 426.5 cm3; (14)Surface Tension: 50.4 dyne/cm; (15)Density: 1.14 g/cm3; (16)Flash Point: 383.4 °C; (17)Enthalpy of Vaporization: 118.69 kJ/mol; (18)Boiling Point: 710.3 °C at 760 mmHg; (19)Vapour Pressure: 2.6E-23 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
1. SMILES: O=C(O)[C@@H]1CCC[C@H]1[C@H]2OC(=O)C[C@H](O)[C@@H](C)C[C@@H](C)C[C@@H](C)C[C@@H]([C@@H](O)C(/C#N)=C\C=C\C2)C
2. InChI: InChI=1/C28H43NO6/c1-17-12-18(2)14-20(4)27(32)21(16-29)8-5-6-11-25(22-9-7-10-23(22)28(33)34)35-26(31)15-24(30)19(3)13-17/h5-6,8,17-20,22-25,27,30,32H,7,9-15H2,1-4H3,(H,33,34)/b6-5+,21-8-/t17-,18+,19-,20-,22+,23+,24-,25-,27+/m0/s1
3. InChIKey: OJCKRNPLOZHAOU-UGKRXNSEBA
4. Std. InChI: InChI=1S/C28H43NO6/c1-17-12-18(2)14-20(4)27(32)21(16-29)8-5-6-11-25(22-9-7-10-23(22)28(33)34)35-26(31)15-24(30)19(3)13-17/h5-6,8,17-20,22-25,27,30,32H,7,9-15H2,1-4H3,(H,33,34)/b6-5+,21-8-/t17-,18+,19-,20-,22+,23+,24-,25-,27+/m0/s1
5. Std. InChIKey: OJCKRNPLOZHAOU-UGKRXNSESA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LD50 intramuscular 74mg/kg (74mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 2, Pg. 1198, 1978.
mouse LD50 intravenous 39mg/kg (39mg/kg)   Journal of Clinical Investigation. Vol. 28, Pg. 1047, 1949.
mouse LD50 subcutaneous 75mg/kg (75mg/kg)   Journal of Clinical Investigation. Vol. 28, Pg. 1047, 1949.
rat LD50 intravenous 2mg/kg (2mg/kg)   "Antibiotics: Origin, Nature, and Properties," Korzyoski, T., et al., eds., Washington, DC, American Soc. for Microbiology, 1978Vol. 2, Pg. 1198, 1978.
rat LD50 subcutaneous 1780ug/kg (1.78mg/kg)   Journal of Clinical Investigation. Vol. 28, Pg. 1047, 1949.