CAS No.61228-92-0,PERIPLANONEB Suppliers

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Basic Information

Molecular Structure:
CAS No.:	61228-92-0
Name:	PERIPLANONEB
Article Data:	6

Formula:	C15H20 O3
Molecular Weight:	248.322
Synonyms:	Spiro[11-oxabicyclo[8.1.0]undec-6-ene-2,2'-oxiran]-3-one,8-methylene-5-(1-methylethyl)-, [1R-(1R,2R,5S,6E,10R)]-; (-)-Periplanone B;Periplanone B
Melting Point:	47-50°
PSA:	42.13000
LogP:	2.27030

Synthetic route

: 70800-65-6, 70831-70-8, 70831-72-0, 70831-75-3, 84236-08-8
(1S,3S,4E,8R,9R,10S)-8,9-epoxy-10,10-epoxymethano-3-isopropyl-6-methylene-4-cyclodecen-1-ol

: 61228-92-0
(3S,8R,9R,10S)-(-)-periplanone-B

Conditions

Conditions	Yield
With dipyridinium dichromate In N,N-dimethyl-formamide for 2h; Ambient temperature;	92%
With dipyridinium dichromate In N,N-dimethyl-formamide	92%
With 3 A molecular sieve; pyridinium chlorochromate In dichloromethane for 1h; Ambient temperature;	88%

: 6814-64-8, 40651-06-7
methylenedimethyl sulfurane

: 105930-41-4
(E)-(1R,5S,10R)-5-Isopropyl-8-methylene-11-oxa-bicyclo[8.1.0]undec-6-ene-2,3-dione

: 61228-92-0
(3S,8R,9R,10S)-(-)-periplanone-B

Conditions

Conditions	Yield
In tetrahydrofuran; dimethyl sulfoxide at 0℃; for 0.166667h;

: 105930-39-0
(4S,5E,9R,10R)-9,10-epoxy-7-methylene-4-(1-methylethyl)-5-cyclodecene-1-one

: 61228-92-0
(3S,8R,9R,10S)-(-)-periplanone-B

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 86 percent / LiN(TMS)2, MoO5HMPAPy / tetrahydrofuran 2: imidazole / dimethylformamide 3: n-BuLi / tetrahydrofuran 4: n-Bu4NF / tetrahydrofuran 5: 92 percent / PDC / dimethylformamide View Scheme
Multi-step reaction with 5 steps 1: 1.) LiN(TMS)2; 2.) MoO5HMPAC5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min 2: dimethylformamide / 16 h / 40 °C 3: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min 4: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature 5: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 1) LiN(TMS)2, 2) MoO5HMPAPy / 1) THF, 30 min, 2) -70 degC, 5 min 2: PCC / CH2Cl2 / 5 h / Ambient temperature; Molecular sieves 3A 3: tetrahydrofuran; dimethylsulfoxide / 0.17 h / 0 °C View Scheme
Multi-step reaction with 5 steps 1: 1) LiN(TMS)2, 2) MoO5HMPApy / 1) -78 deg C, 1 h, THF, 2) -20 deg C, 25 min 2: imidazole / dimethylformamide / 17 h / Ambient temperature 3: 1) n-BuLi / 1) THF, hexane, 10 min, 2a) THF, -15 deg C, 10 min, 2b) 20 min, 0 deg C 4: (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature 5: 92 percent / PDC / dimethylformamide / 2 h / Ambient temperature View Scheme

: 113666-35-6
(2S,4S,5E,9R,10R)-2-t-butyldimethylsilyloxy-9,10-epoxy-7-methylene-4-(1-methylethyl)-5-cyclodecene-1-one

: 61228-92-0
(3S,8R,9R,10S)-(-)-periplanone-B

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: n-BuLi / tetrahydrofuran 2: n-Bu4NF / tetrahydrofuran 3: 92 percent / PDC / dimethylformamide View Scheme
Multi-step reaction with 3 steps 1: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min 2: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature 3: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 1) n-BuLi / 1) THF, hexane, 10 min, 2a) THF, -15 deg C, 10 min, 2b) 20 min, 0 deg C 2: (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature 3: 92 percent / PDC / dimethylformamide / 2 h / Ambient temperature View Scheme

: 70552-76-0, 70614-01-6, 113666-36-7
(1S,3S,4E,8R,9R,10R)-1-t-butyldimethylsilyloxy-8,9-epoxy-6-methylene-10,10-methylenoxy-3-(1-methylethyl)-4-cyclodecene

: 61228-92-0
(3S,8R,9R,10S)-(-)-periplanone-B

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: n-Bu4NF / tetrahydrofuran 2: 92 percent / PDC / dimethylformamide View Scheme
Multi-step reaction with 2 steps 1: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature 2: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature 2: 92 percent / PDC / dimethylformamide / 2 h / Ambient temperature View Scheme

: 123536-67-4
(4S,5E,7S,9R,10R)-9,10-epoxy-7-hydroxymethyl-4-isopropyl-5-cyclodecen-1-one

: 61228-92-0
(3S,8R,9R,10S)-(-)-periplanone-B

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 99 percent / n-Bu3P / tetrahydrofuran 2: 90 percent / H2O2 / tetrahydrofuran 3: 86 percent / LiN(TMS)2, MoO5HMPAPy / tetrahydrofuran 4: imidazole / dimethylformamide 5: n-BuLi / tetrahydrofuran 6: n-Bu4NF / tetrahydrofuran 7: 92 percent / PDC / dimethylformamide View Scheme
Multi-step reaction with 7 steps 1: 99 percent / (n-Bu)3P / tetrahydrofuran / 0.83 h / Ambient temperature 2: 90 percent / 35percent H2O2 / tetrahydrofuran / 13 h / Ambient temperature 3: 1) LiN(TMS)2, 2) MoO5HMPApy / 1) -78 deg C, 1 h, THF, 2) -20 deg C, 25 min 4: imidazole / dimethylformamide / 17 h / Ambient temperature 5: 1) n-BuLi / 1) THF, hexane, 10 min, 2a) THF, -15 deg C, 10 min, 2b) 20 min, 0 deg C 6: (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature 7: 92 percent / PDC / dimethylformamide / 2 h / Ambient temperature View Scheme

Yield

Multi-step reaction with 7 steps
1: 99 percent / n-Bu3P / tetrahydrofuran
2: 90 percent / H2O2 / tetrahydrofuran
3: 86 percent / LiN(TMS)2, MoO5*HMPA*Py / tetrahydrofuran
4: imidazole / dimethylformamide
5: n-BuLi / tetrahydrofuran
6: n-Bu4NF / tetrahydrofuran
7: 92 percent / PDC / dimethylformamide
View Scheme

Multi-step reaction with 7 steps
1: 99 percent / (n-Bu)3P / tetrahydrofuran / 0.83 h / Ambient temperature
2: 90 percent / 35percent H2O2 / tetrahydrofuran / 13 h / Ambient temperature
3: 1) LiN(TMS)2, 2) MoO5*HMPA*py / 1) -78 deg C, 1 h, THF, 2) -20 deg C, 25 min
4: imidazole / dimethylformamide / 17 h / Ambient temperature
5: 1) n-BuLi / 1) THF, hexane, 10 min, 2a) THF, -15 deg C, 10 min, 2b) 20 min, 0 deg C
6: (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature
7: 92 percent / PDC / dimethylformamide / 2 h / Ambient temperature
View Scheme

: 113666-34-5
(2S,4S,5E,9R,10R)-9,10-epoxy-2-hydroxy-7-methylene-4-(1-methylethyl)-5-cyclodecene-1-one

: 61228-92-0
(3S,8R,9R,10S)-(-)-periplanone-B

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: imidazole / dimethylformamide 2: n-BuLi / tetrahydrofuran 3: n-Bu4NF / tetrahydrofuran 4: 92 percent / PDC / dimethylformamide View Scheme
Multi-step reaction with 4 steps 1: dimethylformamide / 16 h / 40 °C 2: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min 3: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature 4: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: imidazole / dimethylformamide / 17 h / Ambient temperature 2: 1) n-BuLi / 1) THF, hexane, 10 min, 2a) THF, -15 deg C, 10 min, 2b) 20 min, 0 deg C 3: (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature 4: 92 percent / PDC / dimethylformamide / 2 h / Ambient temperature View Scheme

: (1S,5S,6R)-5-(2-Ethoxy-ethoxymethyl)-6-((Z)-3-methyl-but-1-enyl)-1-vinyl-cyclohex-2-enol

: 61228-92-0
(3S,8R,9R,10S)-(-)-periplanone-B

Conditions

Conditions	Yield
Multi-step reaction with 10 steps 1: 74 percent / KH, 18-crown-6 / 1,2-dimethoxy-ethane 2: KH, t-BuOOH / tetrahydrofuran 3: PPTS / ethanol 4: 99 percent / n-Bu3P / tetrahydrofuran 5: 90 percent / H2O2 / tetrahydrofuran 6: 86 percent / LiN(TMS)2, MoO5HMPAPy / tetrahydrofuran 7: imidazole / dimethylformamide 8: n-BuLi / tetrahydrofuran 9: n-Bu4NF / tetrahydrofuran 10: 92 percent / PDC / dimethylformamide View Scheme

Yield

Multi-step reaction with 10 steps
1: 74 percent / KH, 18-crown-6 / 1,2-dimethoxy-ethane
2: KH, t-BuOOH / tetrahydrofuran
3: PPTS / ethanol
4: 99 percent / n-Bu3P / tetrahydrofuran
5: 90 percent / H2O2 / tetrahydrofuran
6: 86 percent / LiN(TMS)2, MoO5*HMPA*Py / tetrahydrofuran
7: imidazole / dimethylformamide
8: n-BuLi / tetrahydrofuran
9: n-Bu4NF / tetrahydrofuran
10: 92 percent / PDC / dimethylformamide
View Scheme

: (2Z,6E)-(5S,8S)-5-(2-Ethoxy-ethoxymethyl)-8-isopropyl-cyclodeca-2,6-dienone

: 61228-92-0
(3S,8R,9R,10S)-(-)-periplanone-B

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: KH, t-BuOOH / tetrahydrofuran 2: PPTS / ethanol 3: 99 percent / n-Bu3P / tetrahydrofuran 4: 90 percent / H2O2 / tetrahydrofuran 5: 86 percent / LiN(TMS)2, MoO5HMPAPy / tetrahydrofuran 6: imidazole / dimethylformamide 7: n-BuLi / tetrahydrofuran 8: n-Bu4NF / tetrahydrofuran 9: 92 percent / PDC / dimethylformamide View Scheme

: (E)-(1R,5S,8S,10R)-8-(2-Ethoxy-ethoxymethyl)-5-isopropyl-11-oxa-bicyclo[8.1.0]undec-6-en-2-one

: 61228-92-0
(3S,8R,9R,10S)-(-)-periplanone-B

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1: PPTS / ethanol 2: 99 percent / n-Bu3P / tetrahydrofuran 3: 90 percent / H2O2 / tetrahydrofuran 4: 86 percent / LiN(TMS)2, MoO5HMPAPy / tetrahydrofuran 5: imidazole / dimethylformamide 6: n-BuLi / tetrahydrofuran 7: n-Bu4NF / tetrahydrofuran 8: 92 percent / PDC / dimethylformamide View Scheme

Conditions	Yield
Multi-step reaction with 5 steps 1: 86 percent / LiN(TMS)2, MoO5HMPAPy / tetrahydrofuran 2: imidazole / dimethylformamide 3: n-BuLi / tetrahydrofuran 4: n-Bu4NF / tetrahydrofuran 5: 92 percent / PDC / dimethylformamide View Scheme
Multi-step reaction with 5 steps 1: 1.) LiN(TMS)2; 2.) MoO5HMPAC5H5N / 1.) THF, -70 deg C, 1 h; 2.) -22 deg C, 15 min 2: dimethylformamide / 16 h / 40 °C 3: 1.) n-BuLi / 1. THF, n-hexane, RT, 10 min; 2.) THF, -5 deg C, 10 min 4: n-Bu4NF / tetrahydrofuran / 0.17 h / Ambient temperature 5: 88 percent / PCC, molecular sieves 3A / CH2Cl2 / 1 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: 1) LiN(TMS)2, 2) MoO5HMPAPy / 1) THF, 30 min, 2) -70 degC, 5 min 2: PCC / CH2Cl2 / 5 h / Ambient temperature; Molecular sieves 3A 3: tetrahydrofuran; dimethylsulfoxide / 0.17 h / 0 °C View Scheme
Multi-step reaction with 5 steps 1: 1) LiN(TMS)2, 2) MoO5HMPApy / 1) -78 deg C, 1 h, THF, 2) -20 deg C, 25 min 2: imidazole / dimethylformamide / 17 h / Ambient temperature 3: 1) n-BuLi / 1) THF, hexane, 10 min, 2a) THF, -15 deg C, 10 min, 2b) 20 min, 0 deg C 4: (n-Bu)4NF / tetrahydrofuran / 0.17 h / Ambient temperature 5: 92 percent / PDC / dimethylformamide / 2 h / Ambient temperature View Scheme