Product Name

  • Name

    Brassinolide

  • EINECS
  • CAS No. 72962-43-7
  • Article Data18
  • CAS DataBase
  • Density 1.142 g/cm3
  • Solubility soluble in methanol, ethanol, acetone and tetrahydrofuran
  • Melting Point 200-204 °C
  • Formula C28H48O6
  • Boiling Point 633.716 °C at 760 mmHg
  • Molecular Weight 480.686
  • Flash Point 202.262 °C
  • Transport Information
  • Appearance Off-White Solid
  • Safety 24/25
  • Risk Codes
  • Molecular Structure Molecular Structure of 72962-43-7 (Brassinolide)
  • Hazard Symbols
  • Synonyms B-Homo-7-oxaergostan-6-one,2,3,22,23-tetrahydroxy-, (2a,3a,5a,22R,23R,24S)-;6H-Benz[c]indeno[5,4-e]oxepin-6-one,1-(2,3-dihydroxy-1,4,5-trimethylhexyl)hexadecahydro-8,9-dihydroxy-10a,12a-dimethyl-,[1R-[1a(1S*,2R*,3R*,4S*),3ab,3ba,6ab,8b,9b,10aa,10bb,12aa]]-;Brassinolide (BR);Brassinolide;
  • PSA 107.22000
  • LogP 3.39000

Synthetic route

2α,3α-22R,23R-tetraacetoxy-B-homo-7-oxa-24S-methyl-5α-cholestan-6-one
76987-58-1

2α,3α-22R,23R-tetraacetoxy-B-homo-7-oxa-24S-methyl-5α-cholestan-6-one

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
With potassium hydroxide In methanol for 1h; Heating;94%
With sodium hydroxide In methanol; water for 3h; Heating;57%
With hydrogenchloride; methanol; potassium hydroxide 1.) reflux, 1 h, 2.) room temperature, 1 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps
1: NaOH
2: HCl
View Scheme
(2R,3S,5S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4R,5R)-5-((S)-1,2-Dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-2,3-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-one
83066-72-2

(2R,3S,5S,8S,9S,10R,13S,14S,17R)-17-{(S)-1-[(4R,5R)-5-((S)-1,2-Dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-2,3-dihydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-6-one

A

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

B

(22R,23R,24S)-2α,3α,22,23-tetrahydroxy-6-oxa-7a-homo-5α-campestan-7-one
146205-07-4

(22R,23R,24S)-2α,3α,22,23-tetrahydroxy-6-oxa-7a-homo-5α-campestan-7-one

Conditions
ConditionsYield
With trifluoroacetyl peroxide In dichloromethane at 22℃; for 1h;A 74%
B n/a
(2R,3S,5α,22R,23R,24S)-6,6-Ethylenedioxy-2,3-isopropylidenedioxyergostane-22,23-diol
91708-76-8

(2R,3S,5α,22R,23R,24S)-6,6-Ethylenedioxy-2,3-isopropylidenedioxyergostane-22,23-diol

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
With trifluoroacetyl peroxide; trifluoroacetic acid In chloroform for 3h; Ambient temperature;53%
Multi-step reaction with 3 steps
1: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C
2: pyridine, N,N-dimethylaminopyridine
View Scheme
3-dehydroteasterone
124853-28-7

3-dehydroteasterone

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
With amalgamated zinc; osmium(VIII) oxide; chloro-trimethyl-silane; trifluoroacetyl peroxide; 4-methylmorpholine N-oxide 1.) THF, rt., 12 h; 2.) THF, aq. t-BuOH; 3.) CH2Cl2; Yield given. Multistep reaction;
castasterone
80736-41-0

castasterone

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Yield given. Multistep reaction;
Multi-step reaction with 2 steps
1: pyridine, N,N-dimethylaminopyridine
View Scheme
2,3,22,23-tetra-O-acetylcastasterone
77027-48-6

2,3,22,23-tetra-O-acetylcastasterone

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Yield given. Multistep reaction;
Acetic acid (1R,2R,3S)-2-acetoxy-1-[(S)-1-((1R,3aS,3bS,6aS,8S,9R,10aR,10bS,12aS)-8,9-dihydroxy-10a,12a-dimethyl-6-oxo-hexadecahydro-5-oxa-benzo[3,4]cyclohepta[1,2-e]inden-1-yl)-ethyl]-3,4-dimethyl-pentyl ester
106315-18-8

Acetic acid (1R,2R,3S)-2-acetoxy-1-[(S)-1-((1R,3aS,3bS,6aS,8S,9R,10aR,10bS,12aS)-8,9-dihydroxy-10a,12a-dimethyl-6-oxo-hexadecahydro-5-oxa-benzo[3,4]cyclohepta[1,2-e]inden-1-yl)-ethyl]-3,4-dimethyl-pentyl ester

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
With sodium hydroxide In methanol for 3h; Heating;1.79 g
(1S,2R,4R,5S)-2-[(1R,3aS,4S,5S,7aS)-1-((1S,2R,3R,4S)-2,3-Dihydroxy-1,4,5-trimethyl-hexyl)-4-hydroxymethyl-7a-methyl-octahydro-inden-5-yl]-4,5-dihydroxy-2-methyl-cyclohexanecarboxylic acid

(1S,2R,4R,5S)-2-[(1R,3aS,4S,5S,7aS)-1-((1S,2R,3R,4S)-2,3-Dihydroxy-1,4,5-trimethyl-hexyl)-4-hydroxymethyl-7a-methyl-octahydro-inden-5-yl]-4,5-dihydroxy-2-methyl-cyclohexanecarboxylic acid

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
With hydrogenchloride
(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-{(S)-1-[(4R,5R)-5-((S)-1,2-Dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one
111118-49-1

(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-{(S)-1-[(4R,5R)-5-((S)-1,2-Dimethyl-propyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-ethyl}-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one

A

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

B

(22R,23R,24S)-2α,3α,22,23-tetrahydroxy-6-oxa-7a-homo-5α-campestan-7-one
146205-07-4

(22R,23R,24S)-2α,3α,22,23-tetrahydroxy-6-oxa-7a-homo-5α-campestan-7-one

Conditions
ConditionsYield
Yield given. Multistep reaction. Yields of byproduct given;
(20S)-6,6-ethylenedioxy-2α,3α-isopropylidenedioxy-5α-pregnane-20-carbaldehyde
81481-15-4

(20S)-6,6-ethylenedioxy-2α,3α-isopropylidenedioxy-5α-pregnane-20-carbaldehyde

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1.) n-BuLi, 2.) 30percent H2O2 / 1.) THF, -78 deg C, 3 h, 2.) acetic acid, room temperature, 15 h
2: 85 percent / Ti(O-iPr)4, (+)-L-diethyl tartrate, cumene hydroperoxide, 4 Angstroem MS / CH2Cl2 / 144 h / -25 °C
3: 82 percent / CuCN / diethyl ether / 1.) -78 deg C, 2 h, 2.) 0 deg C, 3 h
4: 53 percent / CF3CO3H, CF3CO2H / CHCl3 / 3 h / Ambient temperature
View Scheme
Multi-step reaction with 8 steps
1: n-BuLi / tetrahydrofuran; hexane / -50 to -60 deg C; -40 deg C, 1 h; -68 to - 65 deg C, 1 h; 0 deg C
2: 74.6 percent / 1.) triphenylphosphine, benzoic acid, diethyl azodicarboxylate; 2.) K2CO3 / 1.) THF, 5-10 deg C, 30 min; 2.) THF/methanol, reflux, 3 h
3: 44.3 g / H2, 1M NaBH4, ethylenediamine, nickel acetate / aq. ethanol / 5 h
4: 93 percent / m-chloroperbenzoic acid, Na2HPO4 / CH2Cl2 / 20 h / 5 °C
5: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h
6: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C
7: pyridine, N,N-dimethylaminopyridine
View Scheme
Multi-step reaction with 7 steps
1: 26.93 g / n-BuLi / tetrahydrofuran; hexane / -50 to -60 deg C; -40 deg C, 1 h; -68 to - 65 deg C, 1 h; 0 deg C
2: 44.3 g / H2, 1M NaBH4, ethylenediamine, nickel acetate / aq. ethanol / 5 h
3: 93 percent / m-chloroperbenzoic acid, Na2HPO4 / CH2Cl2 / 20 h / 5 °C
4: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h
5: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C
6: pyridine, N,N-dimethylaminopyridine
View Scheme
(2α,3α,5α,22S,23E)-6,6-ethylenedioxy-2,3-isopropylidenedioxy-26,27-dinorcholest-23-en-22-ol
148705-11-7

(2α,3α,5α,22S,23E)-6,6-ethylenedioxy-2,3-isopropylidenedioxy-26,27-dinorcholest-23-en-22-ol

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 85 percent / Ti(O-iPr)4, (+)-L-diethyl tartrate, cumene hydroperoxide, 4 Angstroem MS / CH2Cl2 / 144 h / -25 °C
2: 82 percent / CuCN / diethyl ether / 1.) -78 deg C, 2 h, 2.) 0 deg C, 3 h
3: 53 percent / CF3CO3H, CF3CO2H / CHCl3 / 3 h / Ambient temperature
View Scheme
(2R,3S,5α,22R)-23,24-epoxy-6,6-(ethylenedioxy)-2,3-(isopropylidenedioxy)-26,27-dinorcholestan-22-ol
223117-11-1

(2R,3S,5α,22R)-23,24-epoxy-6,6-(ethylenedioxy)-2,3-(isopropylidenedioxy)-26,27-dinorcholestan-22-ol

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 82 percent / CuCN / diethyl ether / 1.) -78 deg C, 2 h, 2.) 0 deg C, 3 h
2: 53 percent / CF3CO3H, CF3CO2H / CHCl3 / 3 h / Ambient temperature
View Scheme
3-methyl-butan-2-one
563-80-4

3-methyl-butan-2-one

ethyl halide

ethyl halide

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: Br2 / methanol
2: acetone / 18 h / Heating
3: NaH / tetrahydrofuran / 0.5 h / 25 °C
4: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
5: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
6: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
7: 96 percent / CSA / 24 h / Ambient temperature
8: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
9: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
Multi-step reaction with 10 steps
1: Br2 / methanol
2: acetone / 18 h / Heating
3: 1.) NaH, triethylphosphonoacetate, 2.) aq. KOH / 1.) THF, 25 deg C, 30 min, 2.) 25 deg C, 24 h
4: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
5: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
6: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
7: 96 percent / CSA / 24 h / Ambient temperature
8: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
9: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
4-(1-methylethyl)furan-2(5H)-one
10547-89-4

4-(1-methylethyl)furan-2(5H)-one

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
2: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
3: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
4: 96 percent / CSA / 24 h / Ambient temperature
5: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
6: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
1-(acetyloxy)-3-methyl-2-butanone
36960-07-3

1-(acetyloxy)-3-methyl-2-butanone

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: NaH / tetrahydrofuran / 0.5 h / 25 °C
2: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
3: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
4: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
5: 96 percent / CSA / 24 h / Ambient temperature
6: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
7: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
Multi-step reaction with 8 steps
1: 1.) NaH, triethylphosphonoacetate, 2.) aq. KOH / 1.) THF, 25 deg C, 30 min, 2.) 25 deg C, 24 h
2: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
3: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
4: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
5: 96 percent / CSA / 24 h / Ambient temperature
6: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
7: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(22E)-stigmasta-2,22-dien-6-one
74174-45-1

(22E)-stigmasta-2,22-dien-6-one

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 72 percent / OsO4, NMO, H2O / acetone; 2-methyl-propan-2-ol / 12 h / Ambient temperature
2: 98 percent / CSA / acetonitrile; CH2Cl2 / 1 h / Ambient temperature
3: OsO4, NMO, aq. NaHCO3, MeSO2NH2 / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 40 °C
4: 82 percent / pyridine, NaHCO3, H5IO6 / tetrahydrofuran / 24 h / Ambient temperature
5: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
6: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
7: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
8: 96 percent / CSA / 24 h / Ambient temperature
9: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
10: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(22E,24S)-3β,5-cyclo-24-ethylcholest-22-en-6-one
74174-49-5

(22E,24S)-3β,5-cyclo-24-ethylcholest-22-en-6-one

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 80 percent / pyridine hydrochloride, LiBr / N,N-dimethyl-acetamide / 4 h / 160 °C
2: 72 percent / OsO4, NMO, H2O / acetone; 2-methyl-propan-2-ol / 12 h / Ambient temperature
3: 98 percent / CSA / acetonitrile; CH2Cl2 / 1 h / Ambient temperature
4: OsO4, NMO, aq. NaHCO3, MeSO2NH2 / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 40 °C
5: 82 percent / pyridine, NaHCO3, H5IO6 / tetrahydrofuran / 24 h / Ambient temperature
6: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
7: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
8: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
9: 96 percent / CSA / 24 h / Ambient temperature
10: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
11: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(22E,24S)-2α,3α-dihydroxy-5α-stigmast-22-en-6-one
81481-12-1

(22E,24S)-2α,3α-dihydroxy-5α-stigmast-22-en-6-one

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 98 percent / CSA / acetonitrile; CH2Cl2 / 1 h / Ambient temperature
2: OsO4, NMO, aq. NaHCO3, MeSO2NH2 / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 40 °C
3: 82 percent / pyridine, NaHCO3, H5IO6 / tetrahydrofuran / 24 h / Ambient temperature
4: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
5: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
6: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
7: 96 percent / CSA / 24 h / Ambient temperature
8: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
9: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(22E,24S)-2α,3α-Dihydroxy-5α-stigmast-22-en-6-one 2,3-acetonide
81481-13-2

(22E,24S)-2α,3α-Dihydroxy-5α-stigmast-22-en-6-one 2,3-acetonide

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: OsO4, NMO, aq. NaHCO3, MeSO2NH2 / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 40 °C
2: 82 percent / pyridine, NaHCO3, H5IO6 / tetrahydrofuran / 24 h / Ambient temperature
3: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
4: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
5: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
6: 96 percent / CSA / 24 h / Ambient temperature
7: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
8: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
Multi-step reaction with 10 steps
1: 83.0 g / p-TsOH / 3 h / Heating
2: 30 g / ozone, NaHCO3 / methanol; CH2Cl2 / 2 h / -60 - -50 °C
3: n-BuLi / tetrahydrofuran; hexane / -50 to -60 deg C; -40 deg C, 1 h; -68 to - 65 deg C, 1 h; 0 deg C
4: 74.6 percent / 1.) triphenylphosphine, benzoic acid, diethyl azodicarboxylate; 2.) K2CO3 / 1.) THF, 5-10 deg C, 30 min; 2.) THF/methanol, reflux, 3 h
5: 44.3 g / H2, 1M NaBH4, ethylenediamine, nickel acetate / aq. ethanol / 5 h
6: 93 percent / m-chloroperbenzoic acid, Na2HPO4 / CH2Cl2 / 20 h / 5 °C
7: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h
8: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C
9: pyridine, N,N-dimethylaminopyridine
View Scheme
Multi-step reaction with 9 steps
1: 83.0 g / p-TsOH / 3 h / Heating
2: 30 g / ozone, NaHCO3 / methanol; CH2Cl2 / 2 h / -60 - -50 °C
3: 26.93 g / n-BuLi / tetrahydrofuran; hexane / -50 to -60 deg C; -40 deg C, 1 h; -68 to - 65 deg C, 1 h; 0 deg C
4: 44.3 g / H2, 1M NaBH4, ethylenediamine, nickel acetate / aq. ethanol / 5 h
5: 93 percent / m-chloroperbenzoic acid, Na2HPO4 / CH2Cl2 / 20 h / 5 °C
6: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h
7: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C
8: pyridine, N,N-dimethylaminopyridine
View Scheme
(22E,24S)-24-ethyl-3α,5-cyclo-5α-cholest-22-en-6-ol
103881-47-6

(22E,24S)-24-ethyl-3α,5-cyclo-5α-cholest-22-en-6-ol

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 13 steps
1: CrO3, H2SO4 / acetone
2: 80 percent / pyridine hydrochloride, LiBr / N,N-dimethyl-acetamide / 4 h / 160 °C
3: 72 percent / OsO4, NMO, H2O / acetone; 2-methyl-propan-2-ol / 12 h / Ambient temperature
4: 98 percent / CSA / acetonitrile; CH2Cl2 / 1 h / Ambient temperature
5: OsO4, NMO, aq. NaHCO3, MeSO2NH2 / tetrahydrofuran; 2-methyl-propan-2-ol / 144 h / 40 °C
6: 82 percent / pyridine, NaHCO3, H5IO6 / tetrahydrofuran / 24 h / Ambient temperature
7: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
8: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
9: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
10: 96 percent / CSA / 24 h / Ambient temperature
11: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
12: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
1-bromo-3-methyl-2-butanone
19967-55-6

1-bromo-3-methyl-2-butanone

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: acetone / 18 h / Heating
2: NaH / tetrahydrofuran / 0.5 h / 25 °C
3: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
4: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
5: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
6: 96 percent / CSA / 24 h / Ambient temperature
7: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
8: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
Multi-step reaction with 9 steps
1: acetone / 18 h / Heating
2: 1.) NaH, triethylphosphonoacetate, 2.) aq. KOH / 1.) THF, 25 deg C, 30 min, 2.) 25 deg C, 24 h
3: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
4: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
5: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
6: 96 percent / CSA / 24 h / Ambient temperature
7: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
8: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(20S)-2α,3α-isopropylidenedioxy-5α-pregnan-6-one-20-carbaldehyde
174656-33-8

(20S)-2α,3α-isopropylidenedioxy-5α-pregnan-6-one-20-carbaldehyde

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
2: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
3: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
4: 96 percent / CSA / 24 h / Ambient temperature
5: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
6: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(3S,4R,5R,6S)-6-((1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-5-Hydroxy-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-1-yl)-3-isopropyl-heptane-1,4,5-triol

(3S,4R,5R,6S)-6-((1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-5-Hydroxy-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-1-yl)-3-isopropyl-heptane-1,4,5-triol

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 96 percent / CSA / 24 h / Ambient temperature
2: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
3: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-((S)-1-{(4R,5R)-5-[(S)-1-(2-Hydroxy-ethyl)-2-methyl-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl)-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-ol

(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-((S)-1-{(4R,5R)-5-[(S)-1-(2-Hydroxy-ethyl)-2-methyl-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-ethyl)-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-ol

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
2: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(S)-3-{(4R,5R)-2,2-Dimethyl-5-[(S)-1-((1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-8,8,10a,12a-tetramethyl-5-oxo-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-1-yl)-ethyl]-[1,3]dioxolan-4-yl}-4-methyl-pentanal
174656-38-3

(S)-3-{(4R,5R)-2,2-Dimethyl-5-[(S)-1-((1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-8,8,10a,12a-tetramethyl-5-oxo-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-1-yl)-ethyl]-[1,3]dioxolan-4-yl}-4-methyl-pentanal

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-((1S,2S,3S,4S)-4-Ethyl-2,3-dihydroxy-1,5-dimethyl-hexyl)-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one
123450-38-4

(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-((1S,2S,3S,4S)-4-Ethyl-2,3-dihydroxy-1,5-dimethyl-hexyl)-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 82 percent / pyridine, NaHCO3, H5IO6 / tetrahydrofuran / 24 h / Ambient temperature
2: 80 percent / LDA / tetrahydrofuran / 1.) -40 to -50 deg C, 30 min, 2.) -75 deg C, 14 h
3: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
4: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
5: 96 percent / CSA / 24 h / Ambient temperature
6: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
7: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-[(1S,2R)-2-Hydroxy-2-((2R,3S)-3-isopropyl-5-oxo-tetrahydro-furan-2-yl)-1-methyl-ethyl]-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one
174656-35-0

(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-[(1S,2R)-2-Hydroxy-2-((2R,3S)-3-isopropyl-5-oxo-tetrahydro-furan-2-yl)-1-methyl-ethyl]-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
2: 96 percent / CSA / 24 h / Ambient temperature
3: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
4: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-[(1S,2R)-2-Hydroxy-2-((R)-3-isopropyl-5-oxo-2,5-dihydro-furan-2-yl)-1-methyl-ethyl]-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one
174656-34-9

(1R,3aS,3bS,5aS,6aS,9aR,10aR,10bS,12aS)-1-[(1S,2R)-2-Hydroxy-2-((R)-3-isopropyl-5-oxo-2,5-dihydro-furan-2-yl)-1-methyl-ethyl]-8,8,10a,12a-tetramethyl-hexadecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 83 percent / H2, pyridine / 10percent Pd/C / ethanol; tetrahydrofuran / 14 h / 2585.7 Torr / Ambient temperature
2: 99 percent / LAH / tetrahydrofuran / 1.) r.t. 2 h, 2.) reflux, overnight
3: 96 percent / CSA / 24 h / Ambient temperature
4: 91 percent / CrO3, pyridine / CH2Cl2 / 48 h / Ambient temperature
5: 72 percent / <(C6H5)3P>3RhCl / benzene / 5 h / Heating
View Scheme
6,6-ethylenedioxy-2α,3α-isopropylidenedioxy-24S-ethyl-5α-cholest-22E-ene
81481-14-3

6,6-ethylenedioxy-2α,3α-isopropylidenedioxy-24S-ethyl-5α-cholest-22E-ene

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 30 g / ozone, NaHCO3 / methanol; CH2Cl2 / 2 h / -60 - -50 °C
2: n-BuLi / tetrahydrofuran; hexane / -50 to -60 deg C; -40 deg C, 1 h; -68 to - 65 deg C, 1 h; 0 deg C
3: 74.6 percent / 1.) triphenylphosphine, benzoic acid, diethyl azodicarboxylate; 2.) K2CO3 / 1.) THF, 5-10 deg C, 30 min; 2.) THF/methanol, reflux, 3 h
4: 44.3 g / H2, 1M NaBH4, ethylenediamine, nickel acetate / aq. ethanol / 5 h
5: 93 percent / m-chloroperbenzoic acid, Na2HPO4 / CH2Cl2 / 20 h / 5 °C
6: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h
7: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C
8: pyridine, N,N-dimethylaminopyridine
View Scheme
Multi-step reaction with 8 steps
1: 30 g / ozone, NaHCO3 / methanol; CH2Cl2 / 2 h / -60 - -50 °C
2: 26.93 g / n-BuLi / tetrahydrofuran; hexane / -50 to -60 deg C; -40 deg C, 1 h; -68 to - 65 deg C, 1 h; 0 deg C
3: 44.3 g / H2, 1M NaBH4, ethylenediamine, nickel acetate / aq. ethanol / 5 h
4: 93 percent / m-chloroperbenzoic acid, Na2HPO4 / CH2Cl2 / 20 h / 5 °C
5: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h
6: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C
7: pyridine, N,N-dimethylaminopyridine
View Scheme
(2R, 3S, 22R, 23S, 24R)-23,24-epoxy-6,6-ethylenedioxy-22-hydroxy-2,3-isopropylidenedioxy-5α-cholestane
86413-56-1

(2R, 3S, 22R, 23S, 24R)-23,24-epoxy-6,6-ethylenedioxy-22-hydroxy-2,3-isopropylidenedioxy-5α-cholestane

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: n-BuLi / hexane; cyclohexane / -70 deg C, 1 h; 10 deg C, 4 h
2: 7.62 g / 80percent AcOH / H2O / 1 h / 50 - 60 °C
3: pyridine, N,N-dimethylaminopyridine
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

acetic anhydride
108-24-7

acetic anhydride

2α,3α-22R,23R-tetraacetoxy-B-homo-7-oxa-24S-methyl-5α-cholestan-6-one
76987-58-1

2α,3α-22R,23R-tetraacetoxy-B-homo-7-oxa-24S-methyl-5α-cholestan-6-one

Conditions
ConditionsYield
With pyridine at 60℃; for 20h; Acetylation;95%
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

acetone
67-64-1

acetone

C34H56O6
220399-01-9

C34H56O6

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 8h; Ambient temperature;91%
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

C34H56O6

C34H56O6

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane Ambient temperature;82%
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

A

Brassinolide

Brassinolide

B

(1R,2R,4R,5S)-2-[(1R,3aS,4S,5S,7aS)-1-((1S,2R,3R,4S)-2,3-Dihydroxy-1,4,5-trimethyl-hexyl)-4-hydroxymethyl-7a-methyl-octahydro-inden-5-yl]-4-hydroxy-2-methyl-6-oxa-bicyclo[3.2.1]octan-7-one

(1R,2R,4R,5S)-2-[(1R,3aS,4S,5S,7aS)-1-((1S,2R,3R,4S)-2,3-Dihydroxy-1,4,5-trimethyl-hexyl)-4-hydroxymethyl-7a-methyl-octahydro-inden-5-yl]-4-hydroxy-2-methyl-6-oxa-bicyclo[3.2.1]octan-7-one

Conditions
ConditionsYield
With methanol; Dowex 50W resin (H(1+)-form); water; sodium methylate 1.) reflux, 5 h, 2.) MeOH, r.t., 3 h; Yield given. Multistep reaction. Yields of byproduct given;
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

2,3,22,33-tetra-O-acetyl-25-hydroxybrassinolide
180961-17-5

2,3,22,33-tetra-O-acetyl-25-hydroxybrassinolide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 61 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 5 h / -30 °C
View Scheme
Multi-step reaction with 2 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 48 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 3 h / 0 °C
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

25-hydroxybrassinolide

25-hydroxybrassinolide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 61 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 5 h / -30 °C
3: 86 percent / KOH / methanol; H2O / 1 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 61 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 5 h / -30 °C
3: 56 percent / KOH / methanol; H2O / 3 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 48 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 3 h / 0 °C
3: 86 percent / KOH / methanol; H2O / 1 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 48 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 3 h / 0 °C
3: 56 percent / KOH / methanol; H2O / 3 h / Heating
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

14α-hydroxybrassinolide

14α-hydroxybrassinolide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 6.5 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 3 h / 0 °C
3: 82 percent / KOH / methanol; H2O / 1 h / 20 °C
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

25-hydroxy-6(6α->3a)abeo-5-epi-brassinolide

25-hydroxy-6(6α->3a)abeo-5-epi-brassinolide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 61 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 5 h / -30 °C
3: 12 percent / KOH / methanol; H2O / 3 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 48 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 3 h / 0 °C
3: 12 percent / KOH / methanol; H2O / 3 h / Heating
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

5-epi-25-hydroxybrassinolide

5-epi-25-hydroxybrassinolide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 61 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 5 h / -30 °C
3: 22 percent / KOH / methanol; H2O / 3 h / Heating
View Scheme
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 48 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 3 h / 0 °C
3: 22 percent / KOH / methanol; H2O / 3 h / Heating
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

14α,25-dihydroxybrassinolide

14α,25-dihydroxybrassinolide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 18 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 3 h / 0 °C
3: 79 percent / KOH / methanol; H2O / 1 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 78 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 24 h / 20 °C
3: 79 percent / KOH / methanol; H2O / 1 h / 20 °C
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

2,3,22,33-tetra-O-acetyl-14α-hydroxybrassinolide

2,3,22,33-tetra-O-acetyl-14α-hydroxybrassinolide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 6.5 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 3 h / 0 °C
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

2,3,22,33-tetra-O-acetyl-25-hydroxy-15-oxo-brassinolide

2,3,22,33-tetra-O-acetyl-25-hydroxy-15-oxo-brassinolide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 3.6 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 3 h / 0 °C
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

2,3,22,33-tetra-O-acetyl-14α,25-dihydroxybrassinolide
215502-60-6

2,3,22,33-tetra-O-acetyl-14α,25-dihydroxybrassinolide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 18 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 3 h / 0 °C
View Scheme
Multi-step reaction with 2 steps
1: 95 percent / pyridine / 20 h / 60 °C
2: 78 percent / methyl(trifluoromethyl)dioxirane; 1,1,1-trifluoroacetone / CH2Cl2 / 24 h / 20 °C
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

(22R,23R,24S)-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergost-2-en-6-one
220398-86-7

(22R,23R,24S)-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergost-2-en-6-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 91 percent / p-TsOH / 8 h / Ambient temperature
2: 86 percent / aq. p-TsOH / dioxane / 4 h / 60 °C
3: 4-dimethylaminopyridine / CH2Cl2 / 2 h / 0 °C
4: triethyl phosphite / 5 h / Heating
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

(22R,23R,24S)-2α,3α-epoxy-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergostan-6-one
220399-03-1

(22R,23R,24S)-2α,3α-epoxy-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergostan-6-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 91 percent / p-TsOH / 8 h / Ambient temperature
2: 86 percent / aq. p-TsOH / dioxane / 4 h / 60 °C
3: 4-dimethylaminopyridine / CH2Cl2 / 2 h / 0 °C
4: triethyl phosphite / 5 h / Heating
5: 50 percent / m-CPBA / CH2Cl2 / 2 h / 0 °C
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

(22R,23R,24S)-2α,3α-dihydroxy-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergostan-6-one
220398-85-6

(22R,23R,24S)-2α,3α-dihydroxy-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergostan-6-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 91 percent / p-TsOH / 8 h / Ambient temperature
2: 86 percent / aq. p-TsOH / dioxane / 4 h / 60 °C
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

(22R,23R,24S)-2α,3β-dihydroxy-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergostan-6-one
220398-88-9

(22R,23R,24S)-2α,3β-dihydroxy-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergostan-6-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 91 percent / p-TsOH / 8 h / Ambient temperature
2: 86 percent / aq. p-TsOH / dioxane / 4 h / 60 °C
3: Et3N, DMAP / CH2Cl2 / 2 h / Ambient temperature
4: pyridinium dichromate, pyridine / 5 h / 70 °C
5: NaBH4 / tetrahydrofuran / 5 h / Ambient temperature
6: tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

(22R,23R,24S)-2β,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one
220401-52-5

(22R,23R,24S)-2β,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 91 percent / p-TsOH / 8 h / Ambient temperature
2: 86 percent / aq. p-TsOH / dioxane / 4 h / 60 °C
3: 4-dimethylaminopyridine / CH2Cl2 / 2 h / 0 °C
4: triethyl phosphite / 5 h / Heating
5: 50 percent / m-CPBA / CH2Cl2 / 2 h / 0 °C
6: 30 percent / aq. HClO4 / dioxane / 5 h / Ambient temperature
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

(22R,23R,24S)-2α,3β,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one

(22R,23R,24S)-2α,3β,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostan-6-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 91 percent / p-TsOH / 8 h / Ambient temperature
2: 86 percent / aq. p-TsOH / dioxane / 4 h / 60 °C
3: Et3N, DMAP / CH2Cl2 / 2 h / Ambient temperature
4: pyridinium dichromate, pyridine / 5 h / 70 °C
5: NaBH4 / tetrahydrofuran / 5 h / Ambient temperature
6: tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature
7: 85 percent / 80 percent aq. AcOH / 2 h / 100 °C
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

C32H50O6S

C32H50O6S

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 91 percent / p-TsOH / 8 h / Ambient temperature
2: 86 percent / aq. p-TsOH / dioxane / 4 h / 60 °C
3: 4-dimethylaminopyridine / CH2Cl2 / 2 h / 0 °C
View Scheme
(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one
72962-43-7

(3α,5α,6α,8β,9α,12β,13β,16α,17β)-10-[(2'α,3'β,4'β,5'β)-3,4-dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

(22R,23R,24S)-2α-t-butyldimethylsiloxy-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergostan-3,6-dione
220398-87-8

(22R,23R,24S)-2α-t-butyldimethylsiloxy-22,23-isopropylidenedioxy-B-homo-7-oxa-5α-ergostan-3,6-dione

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 91 percent / p-TsOH / 8 h / Ambient temperature
2: 86 percent / aq. p-TsOH / dioxane / 4 h / 60 °C
3: Et3N, DMAP / CH2Cl2 / 2 h / Ambient temperature
4: pyridinium dichromate, pyridine / 5 h / 70 °C
View Scheme

Brassinolide Specification

The Brassinolide, with the CAS registry number 72962-43-7, is also known as B-Homo-7-oxaergostan-6-one,2,3,22,23-tetrahydroxy-, (2a,3a,5a,22R,23R,24S)-. It belongs to the product categories of Bio-Pesticide; Intermediates & Fine Chemicals; Pharmaceuticals; Steroids. This chemical's molecular formula is C28H48O6 and molecular weight is 480.68. What's more, its systematic name is (3aS,5S,6R,7aR,7bS,9aS,10R,12aS,12bS)-10-[(2S,3R,4R,5S)-3,4-Dihydroxy-5,6-dimethyl-2-heptanyl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one. Its classification codes are: (1)Growth Substances; (2)Plant Growth Regulators. This chemical is a plant hormone. The first isolated brassinosteroid, it was discovered when it was shown that pollen from rapeseed (Brassica napus) could promote stem elongation and cell division. The biologically active component was isolated and named brassinolide.

Physical properties of Brassinolide are: (1)ACD/LogP: 3.471; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.47; (4)ACD/LogD (pH 7.4): 3.47; (5)ACD/BCF (pH 5.5): 255.94; (6)ACD/BCF (pH 7.4): 255.94; (7)ACD/KOC (pH 5.5): 1842.26; (8)ACD/KOC (pH 7.4): 1842.26; (9)#H bond acceptors: 6; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 107.22 Å2; (13)Index of Refraction: 1.536; (14)Molar Refractivity: 131.257 cm3; (15)Molar Volume: 421.056 cm3; (16)Polarizability: 52.035×10-24cm3; (17)Surface Tension: 45.8 dyne/cm; (18)Density: 1.142 g/cm3; (19)Flash Point: 202.262 °C; (20)Enthalpy of Vaporization: 107.343 kJ/mol; (21)Boiling Point: 633.716 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C3OC[C@H]2[C@@H]1CC[C@@H]([C@@]1(C)CC[C@@H]2[C@@]4(C)C[C@@H](O)[C@@H](O)C[C@H]34)[C@H](C)[C@@H](O)[C@H](O)[C@@H](C)C(C)C
(2)Std. InChI: InChI=1S/C28H48O6/c1-14(2)15(3)24(31)25(32)16(4)18-7-8-19-17-13-34-26(33)21-11-22(29)23(30)12-28(21,6)20(17)9-10-27(18,19)5/h14-25,29-32H,7-13H2,1-6H3/t15-,16-,17-,18+,19-,20-,21+,22-,23+,24+,25+,27+,28+/m0/s1
(3)Std. InChIKey: IXVMHGVQKLDRKH-KNBKMWSGSA-N

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