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Technology Process of (1R,2S,4S,5R,10R,11S)-5-hydroxy-16-[(1S)-1-[(1S,2R,4R,6S)-2-hydroxy-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-4-yl]ethyl]-10-methyl-3-oxapentacyclo[9.8.0.02,4.05,10.014,19]nonadeca-7,14(19),15,17-tetraen-9-one

(1R,2S,4S,5R,10R,11S)-5-hydroxy-16-[(1S)-1-[(1S,2R,4R,6S)-2-hydroxy-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-4-yl]ethyl]-10-methyl-3-oxapentacyclo[9.8.0.02,4.05,10.014,19]nonadeca-7,14(19),15,17-tetraen-9-one

Base Information
  • Chemical Name:(1R,2S,4S,5R,10R,11S)-5-hydroxy-16-[(1S)-1-[(1S,2R,4R,6S)-2-hydroxy-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-4-yl]ethyl]-10-methyl-3-oxapentacyclo[9.8.0.02,4.05,10.014,19]nonadeca-7,14(19),15,17-tetraen-9-one
  • CAS No.:40071-64-5
  • Molecular Formula:C28H34O6
  • Molecular Weight:466.57
  • Hs Code.:
  • DSSTox Substance ID:DTXSID60960530
  • Metabolomics Workbench ID:136466
(1R,2S,4S,5R,10R,11S)-5-hydroxy-16-[(1S)-1-[(1S,2R,4R,6S)-2-hydroxy-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-4-yl]ethyl]-10-methyl-3-oxapentacyclo[9.8.0.02,4.05,10.014,19]nonadeca-7,14(19),15,17-tetraen-9-one

Synonyms:nicandrenone

Suppliers and Price of (1R,2S,4S,5R,10R,11S)-5-hydroxy-16-[(1S)-1-[(1S,2R,4R,6S)-2-hydroxy-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-4-yl]ethyl]-10-methyl-3-oxapentacyclo[9.8.0.02,4.05,10.014,19]nonadeca-7,14(19),15,17-tetraen-9-one
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Chemical Property of (1R,2S,4S,5R,10R,11S)-5-hydroxy-16-[(1S)-1-[(1S,2R,4R,6S)-2-hydroxy-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-4-yl]ethyl]-10-methyl-3-oxapentacyclo[9.8.0.02,4.05,10.014,19]nonadeca-7,14(19),15,17-tetraen-9-one
Chemical Property:
  • Vapor Pressure:1.59E-16mmHg at 25°C 
  • Melting Point:119 °C(Solv: hexane (110-54-3)) 
  • Boiling Point:625.8°C at 760 mmHg 
  • PKA:12.51±0.70(Predicted) 
  • Flash Point:208.7°C 
  • PSA：91.82000 
  • Density:1.347g/cm3 
  • LogP:3.13840 
  • XLogP3:2.5
  • Hydrogen Bond Donor Count:2
  • Hydrogen Bond Acceptor Count:6
  • Rotatable Bond Count:2
  • Exact Mass:466.23553880
  • Heavy Atom Count:34
  • Complexity:949
Purity/Quality:
Safty Information:
  • Pictogram(s):  
  • Hazard Codes: 
MSDS Files:

SDS file from LookChem

Useful:
  • Canonical SMILES:CC(C1CC2(C(O2)(C(O1)O)C)C)C3=CC4=C(C=C3)C5C(CC4)C6(C(=O)C=CCC6(C7C5O7)O)C
  • Isomeric SMILES:C[C@H]([C@H]1C[C@]2([C@](O2)([C@@H](O1)O)C)C)C3=CC4=C(C=C3)[C@H]5[C@H](CC4)[C@]6(C(=O)C=CC[C@@]6([C@@H]7[C@H]5O7)O)C
Technology Process of (1R,2S,4S,5R,10R,11S)-5-hydroxy-16-[(1S)-1-[(1S,2R,4R,6S)-2-hydroxy-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-4-yl]ethyl]-10-methyl-3-oxapentacyclo[9.8.0.02,4.05,10.014,19]nonadeca-7,14(19),15,17-tetraen-9-one

There total 28 articles about (1R,2S,4S,5R,10R,11S)-5-hydroxy-16-[(1S)-1-[(1S,2R,4R,6S)-2-hydroxy-1,6-dimethyl-3,7-dioxabicyclo[4.1.0]heptan-4-yl]ethyl]-10-methyl-3-oxapentacyclo[9.8.0.02,4.05,10.014,19]nonadeca-7,14(19),15,17-tetraen-9-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

Acetic acid (1S,4R,6S)-4-[(S)-1-((1aS,1bR,5aR,5bS,11bR,11cS)-1b-hydroxy-5a-methyl-5-oxo-1a,1b,2,5,5a,5b,6,7,11b,11c-decahydro-1-oxa-cyclopropa[g]chrysen-9-yl)-ethyl]-1,6-dimethyl-3,7-dioxa-bicyclo[4.1.0]hept-2-yl ester

Acetic acid (1S,4R,6S)-4-[(S)-1-((1aS,1bR,5aR,5bS,11bR,11cS)-1b-hydroxy-5a-methyl-5-oxo-1a,1b,2,5,5a,5b,6,7,11b,11c-decahydro-1-oxa-cyclopropa[g]chrysen-9-yl)-ethyl]-1,6-dimethyl-3,7-dioxa-bicyclo[4.1.0]hept-2-yl ester

nicandrenone
40071-64-5

nicandrenone

Guidance literature:
With potassium carbonate; In methanol; water; at 25 ℃; for 0.25h;
DOI:10.1021/ja0024892

Reference yield:

(2R,4bR)-8-Allyloxy-2-(dimethyl-phenyl-silanyl)-4a-methyl-11-triethylsilanyloxy-2,3,4a,4b,5,6,12,12a-octahydro-1H-chrysen-4-one

(2R,4bR)-8-Allyloxy-2-(dimethyl-phenyl-silanyl)-4a-methyl-11-triethylsilanyloxy-2,3,4a,4b,5,6,12,12a-octahydro-1H-chrysen-4-one

nicandrenone
40071-64-5

nicandrenone

Guidance literature:
Multi-step reaction with 28 steps
1.1: 90 percent / LiAlH4 / diethyl ether / 0.5 h / -78 °C
2.1: 92 percent / i-Pr2NEt / CH2Cl2 / 46 h / 23 °C
3.1: 89 percent / p-TsOH / CH2Cl2; methanol / 0.08 h / 23 °C
4.1: LDA / tetrahydrofuran / 0.33 h / -78 °C
5.1: 856 mg / O2; Pd(OAc)2; 2,6-di-tert-butyl-4-methylpyridine / dimethylsulfoxide / 12 h / 25 °C
6.1: L-selectride / tetrahydrofuran / 0.33 h / -78 °C
7.1: 564 mg / t-BuOOH; VO(acac)2 / CH2Cl2; decane / 20 h / 0 °C
8.1: 97 percent / Et3N; DMAP / CH2Cl2 / 3 h / 25 °C
9.1: Pd(Ph3P)4; Et2NH / CH2Cl2 / 3 h / Heating
10.1: 690 mg / Et3N / CH2Cl2 / 18 h / 23 °C
11.1: H2; AcOH / Pd/C / ethyl acetate / 7 h / 23 °C / 760.05 Torr
12.1: 560 mg / Dess-Martin periodinane / CH2Cl2 / 2 h / 23 °C
13.1: 91 percent / K2CO3 / methanol; H2O; CH2Cl2 / 2.5 h / 25 °C
14.1: MgI2; NaI / CH2Cl2; acetonitrile / 0.17 h / 0 °C
15.1: CH2Cl2; acetonitrile / 0.17 h / 0 °C
15.2: 72 percent / methanesulfonyl chloride; Et3N / CH2Cl2 / 1.5 h / -66 - 25 °C
16.1: 76 percent / t-BuOOH; VO(acac)2 / CH2Cl2; decane / 44 h / 0 °C
17.1: 74 percent / LiCl; CuCl / Pd(PPh)3 / dimethylsulfoxide / 46 h / 20 - 60 °C
18.1: H2 / Rh(nbd)(dppb)BF4 / CH2Cl2 / 45 h / 0 °C / 760.05 Torr
19.1: 18 mg / t-BuOOH; VO(acac)2 / CH2Cl2; decane / 2 h / 0 °C
20.1: TBAF / tetrahydrofuran / 0.08 h / 0 °C
21.1: 6.0 mg / aq. NaOCl; TEMPO; KBr / CH2Cl2; H2O / 0.17 h / 0 °C
22.1: Hg(OAc)2; AcOOH; AcOH / 3 h / 25 °C
23.1: Et3N; DMAP / CH2Cl2 / 0.25 h
24.1: 7.0 mg / DBU / CH2Cl2 / 2.5 h / 25 °C
25.1: DIBAL / toluene / 0.08 h / -78 °C
26.1: Et3N; DMAP / CH2Cl2 / 0.75 h
27.1: Dess-Martin periodinane / CH2Cl2 / 14 h / Heating
28.1: K2CO3 / methanol; H2O / 0.25 h / 25 °C
With tert.-butylhydroperoxide; peracetic acid; dmap; palladium diacetate; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium(0); 2,6-di-tert-butyl-4-methylpyridine; bis(acetylacetonate)oxovanadium; mercury(II) diacetate; tetrabutyl ammonium fluoride; hydrogen; oxygen; L-Selectride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; copper(l) chloride; lithium chloride; potassium bromide; magnesium iodide; lithium diisopropyl amide; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium(0); {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF4; In tetrahydrofuran; methanol; diethyl ether; decane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; acetonitrile; 17.1: Stille reaction;
DOI:10.1021/ja0024892

Reference yield:

(4bR,8R,10S,10aR,10bS)-2-Allyloxy-10-benzyloxymethoxy-8-(dimethyl-phenyl-silanyl)-10a-methyl-7,8,9,10,10a,10b,11,12-octahydro-4bH-chrysen-5-one
303998-25-6

(4bR,8R,10S,10aR,10bS)-2-Allyloxy-10-benzyloxymethoxy-8-(dimethyl-phenyl-silanyl)-10a-methyl-7,8,9,10,10a,10b,11,12-octahydro-4bH-chrysen-5-one

nicandrenone
40071-64-5

nicandrenone

Guidance literature:
Multi-step reaction with 23 steps
1.1: L-selectride / tetrahydrofuran / 0.33 h / -78 °C
2.1: 564 mg / t-BuOOH; VO(acac)2 / CH2Cl2; decane / 20 h / 0 °C
3.1: 97 percent / Et3N; DMAP / CH2Cl2 / 3 h / 25 °C
4.1: Pd(Ph3P)4; Et2NH / CH2Cl2 / 3 h / Heating
5.1: 690 mg / Et3N / CH2Cl2 / 18 h / 23 °C
6.1: H2; AcOH / Pd/C / ethyl acetate / 7 h / 23 °C / 760.05 Torr
7.1: 560 mg / Dess-Martin periodinane / CH2Cl2 / 2 h / 23 °C
8.1: 91 percent / K2CO3 / methanol; H2O; CH2Cl2 / 2.5 h / 25 °C
9.1: MgI2; NaI / CH2Cl2; acetonitrile / 0.17 h / 0 °C
10.1: CH2Cl2; acetonitrile / 0.17 h / 0 °C
10.2: 72 percent / methanesulfonyl chloride; Et3N / CH2Cl2 / 1.5 h / -66 - 25 °C
11.1: 76 percent / t-BuOOH; VO(acac)2 / CH2Cl2; decane / 44 h / 0 °C
12.1: 74 percent / LiCl; CuCl / Pd(PPh)3 / dimethylsulfoxide / 46 h / 20 - 60 °C
13.1: H2 / Rh(nbd)(dppb)BF4 / CH2Cl2 / 45 h / 0 °C / 760.05 Torr
14.1: 18 mg / t-BuOOH; VO(acac)2 / CH2Cl2; decane / 2 h / 0 °C
15.1: TBAF / tetrahydrofuran / 0.08 h / 0 °C
16.1: 6.0 mg / aq. NaOCl; TEMPO; KBr / CH2Cl2; H2O / 0.17 h / 0 °C
17.1: Hg(OAc)2; AcOOH; AcOH / 3 h / 25 °C
18.1: Et3N; DMAP / CH2Cl2 / 0.25 h
19.1: 7.0 mg / DBU / CH2Cl2 / 2.5 h / 25 °C
20.1: DIBAL / toluene / 0.08 h / -78 °C
21.1: Et3N; DMAP / CH2Cl2 / 0.75 h
22.1: Dess-Martin periodinane / CH2Cl2 / 14 h / Heating
23.1: K2CO3 / methanol; H2O / 0.25 h / 25 °C
With tert.-butylhydroperoxide; peracetic acid; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; tetrakis(triphenylphosphine) palladium(0); bis(acetylacetonate)oxovanadium; mercury(II) diacetate; tetrabutyl ammonium fluoride; hydrogen; L-Selectride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; diethylamine; triethylamine; sodium iodide; copper(l) chloride; lithium chloride; potassium bromide; magnesium iodide; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium(0); {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF4; In tetrahydrofuran; methanol; decane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; acetonitrile; 12.1: Stille reaction;
DOI:10.1021/ja0024892
upstream raw materials:

NIC-1 lactone

(4bR,8R,10S,10aR,10bS)-2-Allyloxy-10-benzyloxymethoxy-8-(dimethyl-phenyl-silanyl)-10a-methyl-7,8,9,10,10a,10b,11,12-octahydro-4bH-chrysen-5-one

(4bR,6aR,8R,10S,10aS,10bS)-2-Allyloxy-10-benzyloxymethoxy-8-(dimethyl-phenyl-silanyl)-10a-methyl-6,6a,7,8,9,10,10a,10b,11,12-decahydro-4bH-chrysen-5-one

(2R,4S,4aS,4bR,12aR)-8-Allyloxy-2-(dimethyl-phenyl-silanyl)-4a-methyl-11-triethylsilanyloxy-1,2,3,4,4a,4b,5,6,12,12a-decahydro-chrysen-4-ol

Refernces

Enantioselective total synthesis of nicandrenones [10]

10.1021/ja0024892

The study presents the first enantioselective total synthesis of nicandrenones, a family of structurally complex, steroid-derived natural products found in Nicandra physaloides, a plant known for its insect repellent and antifeedant properties. The synthesis approach was both enantio- and diastereoselective, focusing on the creation of nicandrenones NIC-1 lactone (1), NIC-1 (2), and NIC-10 (3). Key chemicals used in the study included diene 55, chiral R,β-enone 46, methylaluminum dichloride for an exo-selective Diels-Alder reaction to generate the tetracyclic nicandrenone nucleus; LiAlH4 for reduction, BOM-Cl for ether formation, and Pd(OAc)2 for enone formation. Other reagents such as tBuOOH, VO(acac)2 for epoxidation, and various palladium catalysts for coupling reactions were also utilized. The purpose of these chemicals was to construct the complex molecular structure of nicandrenones through a series of reactions, including ring formation, functional group transformations, and selective reductions, ultimately achieving the total synthesis of the target compounds.

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