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Basic Information
CAS No.: 131929-60-7
Name: SPINOSAD
Molecular Structure:
Molecular Structure of 131929-60-7 (SPINOSAD)
Formula: C41H65NO10
Molecular Weight: 731.968
Synonyms: (-)-SpinosynA;A 83543A;Lepicidin A;Spinosyn A;
EINECS: 620-162-1
Density: 1.167 g/cm3
Melting Point: 84oC to 99.5oC
Boiling Point: 801.515 °C at 760 mmHg
Flash Point: 438.541 °C
Solubility: Spinosyn A: 290 mg l-1 (pH 5); Spinosyn D: 29 mg l-1 (pH 5)
Transport Information: UN 3077
PSA: 111.22000
LogP: 5.48740
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Synthetic route

Dimethyl-[(2R,3S)-2-methyl-6-(pyrimidin-2-ylsulfanyl)-tetrahydro-pyran-3-yl]-amine

131929-68-5

(2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-9-ethyl-13-hydroxy-14-methyl-2-(((2R,3R,5S,6S)-3,4,5-trimethoxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-3,3a,5b,6,9,10,11,12,13,14,16a,16b-dodecahydro-1H-as-indaceno[3,2-d][1]oxacyclododecine-7,15(2H,5aH)-dione

A

131929-60-7

spinosyn A

B

C41H65NO10

Conditions
ConditionsYield
With silver trifluoromethanesulfonate In dichloromethane for 3h; Yield given. Yields of byproduct given;
...Expand
6026-86-4

methyl 4-formylbutanoate

131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 16 steps
1: (-)-(1S,2R)-N,N-dibutylnorephedrine / hexane; toluene / 72 h / 0 °C
2: 84 percent / 2,6-lutidine / CH2Cl2 / 2 h / Ambient temperature
3: 94 percent / DIBAL-H / CH2Cl2; toluene / 0.5 h / -78 °C
4: 1.) Bu2BOTf, Et3N / 1.) CH2Cl2, from 0 to 5 deg C, 20 min, 2.) CH2Cl2, from -78 to 0 deg C, 3 h
5: 1.41 g / DMAP / CH2Cl2 / 144 h / Ambient temperature
6: 30percent aq. H2O2, LiOH / H2O; tetrahydrofuran; dimethylformamide / 0 °C
7: oxalyl chloride / dimethylformamide; hexane / 0.75 h / Ambient temperature
8: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
9: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
10: Jones reagent / acetone / 1.5 h / 0 °C
11: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
12: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
13: 63 percent / methanolic K2CO3 / 48 h / Heating
14: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
15: 91 percent / 49percent aq. HF / acetonitrile / 24 h
16: AgOTf3 / CH2Cl2 / 3 h
View Scheme
56587-30-5

D-forosamine

131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) diethyl azodicarboxylate, PPh3 / 1.) THF, -50 deg C, 10 min, 2.) THF, from -50 to 20 deg C, 3 h
2: AgOTf3 / CH2Cl2 / 3 h
View Scheme
118545-01-0

(S)-5-Hydroxy-heptanoic acid methyl ester

131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1: 84 percent / 2,6-lutidine / CH2Cl2 / 2 h / Ambient temperature
2: 94 percent / DIBAL-H / CH2Cl2; toluene / 0.5 h / -78 °C
3: 1.) Bu2BOTf, Et3N / 1.) CH2Cl2, from 0 to 5 deg C, 20 min, 2.) CH2Cl2, from -78 to 0 deg C, 3 h
4: 1.41 g / DMAP / CH2Cl2 / 144 h / Ambient temperature
5: 30percent aq. H2O2, LiOH / H2O; tetrahydrofuran; dimethylformamide / 0 °C
6: oxalyl chloride / dimethylformamide; hexane / 0.75 h / Ambient temperature
7: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
8: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
9: Jones reagent / acetone / 1.5 h / 0 °C
10: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
11: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
12: 63 percent / methanolic K2CO3 / 48 h / Heating
13: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
14: 91 percent / 49percent aq. HF / acetonitrile / 24 h
15: AgOTf3 / CH2Cl2 / 3 h
View Scheme
155189-82-5

13,14β-Dihydro A83543A aglycon 9α,17α-bis-O-(TBDMS) ether

131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 19 steps
1: t-BuOOH, Triton B / methanol; H2O; tetrahydrofuran / 120 h / Ambient temperature
2: diethyl ether / 0 °C
3: 87 percent / LiAlH4 / diethyl ether / 1 h / Ambient temperature
4: 85 percent / NaIO4 / tetrahydrofuran; H2O / Ambient temperature
5: 1.) KHMDS / 1.) THF, toluene, a) -78 deg C, 15 min, b) RT, 1.5 h, 2.) THF, toluene, from 0 to 20 deg C, 2 h
6: 1.) MCPBA, NaHCO3, 2.) TBAF, 3.) NaIO4
7: 90 percent / pyridine, DMAP
8: MeOH / 168 h / Heating
9: camphorsulfonic acid / CH2Cl2 / 24 h
10: 1.) KHMDS / 1.) toluene, THF, -78 deg C, 30 min, 2.) toluene, THF, from -78 deg C to RT, 4 h
11: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
12: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
13: Jones reagent / acetone / 1.5 h / 0 °C
14: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
15: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
16: 63 percent / methanolic K2CO3 / 48 h / Heating
17: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
18: 91 percent / 49percent aq. HF / acetonitrile / 24 h
19: AgOTf3 / CH2Cl2 / 3 h
View Scheme
204381-35-1

(S)-5-(tert-butyldimethylsiloxy)heptanal

131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 1.) Bu2BOTf, Et3N / 1.) CH2Cl2, from 0 to 5 deg C, 20 min, 2.) CH2Cl2, from -78 to 0 deg C, 3 h
2: 1.41 g / DMAP / CH2Cl2 / 144 h / Ambient temperature
3: 30percent aq. H2O2, LiOH / H2O; tetrahydrofuran; dimethylformamide / 0 °C
4: oxalyl chloride / dimethylformamide; hexane / 0.75 h / Ambient temperature
5: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
6: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
7: Jones reagent / acetone / 1.5 h / 0 °C
8: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
9: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
10: 63 percent / methanolic K2CO3 / 48 h / Heating
11: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
12: 91 percent / 49percent aq. HF / acetonitrile / 24 h
13: AgOTf3 / CH2Cl2 / 3 h
View Scheme
204381-34-0

(S)-5-(tert-Butyl-dimethyl-silanyloxy)-heptanoic acid methyl ester

131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 14 steps
1: 94 percent / DIBAL-H / CH2Cl2; toluene / 0.5 h / -78 °C
2: 1.) Bu2BOTf, Et3N / 1.) CH2Cl2, from 0 to 5 deg C, 20 min, 2.) CH2Cl2, from -78 to 0 deg C, 3 h
3: 1.41 g / DMAP / CH2Cl2 / 144 h / Ambient temperature
4: 30percent aq. H2O2, LiOH / H2O; tetrahydrofuran; dimethylformamide / 0 °C
5: oxalyl chloride / dimethylformamide; hexane / 0.75 h / Ambient temperature
6: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
7: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
8: Jones reagent / acetone / 1.5 h / 0 °C
9: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
10: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
11: 63 percent / methanolic K2CO3 / 48 h / Heating
12: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
13: 91 percent / 49percent aq. HF / acetonitrile / 24 h
14: AgOTf3 / CH2Cl2 / 3 h
View Scheme
204381-32-8

Formic acid 2-((3S,3aR,5aS,7R,8aR,8bS)-7-hydroxy-2-oxo-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-3-yl)-ethyl ester

131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: 90 percent / pyridine, DMAP
2: MeOH / 168 h / Heating
3: camphorsulfonic acid / CH2Cl2 / 24 h
4: 1.) KHMDS / 1.) toluene, THF, -78 deg C, 30 min, 2.) toluene, THF, from -78 deg C to RT, 4 h
5: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
6: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
7: Jones reagent / acetone / 1.5 h / 0 °C
8: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
9: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
10: 63 percent / methanolic K2CO3 / 48 h / Heating
11: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
12: 91 percent / 49percent aq. HF / acetonitrile / 24 h
13: AgOTf3 / CH2Cl2 / 3 h
View Scheme
204381-30-6

(2R,3aS,5aR,5bS,10aS,10bR)-2-(tert-Butyl-dimethyl-silanyloxy)-2,3,3a,5a,5b,6,7,9,9a,10,10a,10b-dodecahydro-1H-8-oxa-cyclopenta[a]fluoren-9-ol

131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 15 steps
1: 1.) KHMDS / 1.) THF, toluene, a) -78 deg C, 15 min, b) RT, 1.5 h, 2.) THF, toluene, from 0 to 20 deg C, 2 h
2: 1.) MCPBA, NaHCO3, 2.) TBAF, 3.) NaIO4
3: 90 percent / pyridine, DMAP
4: MeOH / 168 h / Heating
5: camphorsulfonic acid / CH2Cl2 / 24 h
6: 1.) KHMDS / 1.) toluene, THF, -78 deg C, 30 min, 2.) toluene, THF, from -78 deg C to RT, 4 h
7: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
8: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
9: Jones reagent / acetone / 1.5 h / 0 °C
10: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
11: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
12: 63 percent / methanolic K2CO3 / 48 h / Heating
13: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
14: 91 percent / 49percent aq. HF / acetonitrile / 24 h
15: AgOTf3 / CH2Cl2 / 3 h
View Scheme

2,2-Dimethyl-propionic acid (2R,3aS,5aR,6S,8aS,8bR)-6-(2-hydroxy-ethyl)-7-oxo-1,2,3,3a,5a,6,7,8,8a,8b-decahydro-as-indacen-2-yl ester

131929-60-7

spinosyn A

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: camphorsulfonic acid / CH2Cl2 / 24 h
2: 1.) KHMDS / 1.) toluene, THF, -78 deg C, 30 min, 2.) toluene, THF, from -78 deg C to RT, 4 h
3: 1.) Me3SnSnMe3, (Ph3P)4Pd, LiCl, 2.) Pd2(dba)3*CHCl3, (i-Pr)2NEt / 1.) THF, 60 deg C, 2 d, 2.) benzene, RT, 6 h
4: DDQ, phosphate buffer / CH2Cl2 / 2 h / 0 °C
5: Jones reagent / acetone / 1.5 h / 0 °C
6: aq. AcOH / tetrahydrofuran / 24 h / 0 - 20 °C
7: 2,4,6-trichlorobenzoyl chlorie, DMAP, Et3N / benzene
8: 63 percent / methanolic K2CO3 / 48 h / Heating
9: 85 percent / trityl perchlorate / toluene / 3.17 h / 0 - 20 °C
10: 91 percent / 49percent aq. HF / acetonitrile / 24 h
11: AgOTf3 / CH2Cl2 / 3 h
View Scheme
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  • 131929-60-7 C41H65NO10 SPINOSAD

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Chemistry

 Lepicidin A with CAS NO. of  131929-60-7 is also called for Spinosyn A ; (2R,3aS,5aR,5bS,9S,13S,14R,16aS,16bR)-2-((6-Deoxy-2,3,4-tri-O-methyl-alpha-L-mannopyranosyl)oxy)-13-(((2R,5S,6R)-5-(dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl)oxy)-9-ethyl-14-methyl-2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-tetradecahydro-1H-as-indaceno(3,2-d)oxacyclododecin-7,15-dione ; A 83543A ; CCRIS 8937 ; HSDB 7006 ; LY-232105 ; PP-105 ; Spinosad factor A ; UNII-OY0L59V61N ; 1H-as-Indaceno(3,2-d)oxacyclododecin-7,15-dione, 2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-tetradecahydro-2-((6-deoxy-2,3,4-tri-O-methyl-alpha-L-mannopyranosyl)oxy)- 13-((5-dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl)oxy)-9-ethyl-14-methyl-, (2R-(2R*,3aS*,5aR*,5bS*,9S*,13S*(2R*,5S*,6R*),14R*,16aS*,16bR*))- ; 1H-as-Indaceno(3,2-d)oxacyclododecin-7,15-dione, 2-((6-deoxy-2,3,4-tri-O-methyl-alpha-L-mannopyranosyl)oxy)-13-(((2R,5S,6R)-5-(dimethylamino)tetrahydro-6-methyl-2H-pyran-2-yl)oxy)-9-ethyl-2,3,3a,5a,5b,6,9,10,11,12,13,14,16a,16b-tetradecahydro-14-methyl-,(2R,3aS,5aR,5bS,9S,13S, 14R ,16aS, 16bR) -  and so on.
Molecular Formula: C41H65NO10
Molecular Weight: 731.96
ACD/LogP: 4.80  
ACD/LogD (pH 5.5): 1.99 
ACD/LogD (pH 7.4): 3.56 
ACD/BCF (pH 5.5): 4.06 
ACD/BCF (pH 7.4): 151.13 
ACD/KOC (pH 5.5): 15.11 
ACD/KOC (pH 7.4): 562.62 
H bond acceptors: 11 
H bond donors: 0 
Freely Rotating Bonds: 9
Heavy Atom Count: 52
Formal Charge: 0
Complexity: 1290
Isotope Atom Count: 0
Defined Atom StereoCenter Count: 16
Undefined Atom StereoCenter Count: 1
Defined Bond StereoCenter Count: 0
Undefined Bond StereoCenter Count: 0
Covalently-Bonded Unit Count: 1
Index of Refraction: 1.54 
Molar Refractivity: 196.9 cm3 
Molar Volume: 627.2 cm3 
Surface Tension: 45.8 dyne/cm 
Density: 1.16 g/cm3 
Flash Point: 438.5°C 
Enthalpy of Vaporization: 116.54 kJ/mol 
Boiling Point: 801.5°C at 760 mmHg 
Vapour Pressure: 1.04E-25 mmHg at 25°C 
The molecular structure of Lepicidin A with CAS NO. of  131929-60-7:

Uses

 Lepicidin A with CAS NO. of  131929-60-7 is used as pediculicide.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD oral > 400mg/kg (400mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING National Technical Information Service. Vol. OTS0543604,
mouse LDLo oral 500mg/kg (500mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) National Technical Information Service. Vol. OTS0543562,
rat LC50 inhalation > 499mg/m3/4H (499mg/m3) SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER		 National Technical Information Service. Vol. OTS0534564,
rat LD oral > 2gm/kg (2000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER		 National Technical Information Service. Vol. OTS0543570,

Safety Profile

Moderately toxic by ingestion and inhalation. When heated to decomposition it emits toxic vapors of NOx.
RIDADR:  3077
HazardClass:  9
PackingGroup:  III
Hazardous Substances Data: 131929-60-7(Hazardous Substances Data)