(1'R,5'S,6'S,9'S,10'S,13'R)-5'-Methyl-6'-prop-1-ynylspiro[1,3-dioxolane-2,15'-18-oxapentacyclo[11.4.1.01,13.02,10.05,9]octadec-2-ene]-6'-ol

Base Information

• Chemical Name: (1'R,5'S,6'S,9'S,10'S,13'R)-5'-Methyl-6'-prop-1-ynylspiro[1,3-dioxolane-2,15'-18-oxapentacyclo[11.4.1.01,13.02,10.05,9]octadec-2-ene]-6'-ol
• CAS No.: 84371-57-3
• Molecular Formula: C23H30O4
• Molecular Weight: 370.489
• UNII: JM7HCL46CC
• DSSTox Substance ID: DTXSID30441604
• Nikkaji Number: J697.341H
• Wikidata: Q82258423
• Mol file: 84371-57-3.mol

Synonyms:84371-57-3;(1'R,5'S,6'S,9'S,10'S,13'R)-5'-Methyl-6'-prop-1-ynylspiro[1,3-dioxolane-2,15'-18-oxapentacyclo[11.4.1.01,13.02,10.05,9]octadec-2-ene]-6'-ol;ZINC04073589;JM7HCL46CC;SCHEMBL10877775;DTXSID30441604;NRUIWWWJNIPUBD-XZJZWBLTSA-N;(5|A,10|A,17|A)-5,10-Epoxy-17-hydroxy-17-(1-propyn-1-yl)-estr-9(11)-en-3-one Cyclic 1,2-Ethanediyl Acetal;5,10alpha-Epoxy-3,3-(ethylenebisoxy)-17-(1-propynyl)-5alpha-estr-9(11)-en-17beta-ol;(5?,10?,17?)-5,10-Epoxy-17-hydroxy-17-(1-propyn-1-yl)-estr-9(11)-en-3-one Cyclic 1,2-Ethanediyl Acetal;5alpha,10alpha-Epoxy-3,3-(ethylenedioxy)-17beta-hydroxy-17alpha-(1-propynyl)-9(11)-estrene;Estr-9(11)-en-3-one, 5,10-epoxy-17-hydroxy-17-(1-propyn-1-yl)-, cyclic 1,2-ethanediyl acetal, (5alpha,10alpha,17beta)-

Chemical Property of (1'R,5'S,6'S,9'S,10'S,13'R)-5'-Methyl-6'-prop-1-ynylspiro[1,3-dioxolane-2,15'-18-oxapentacyclo[11.4.1.01,13.02,10.05,9]octadec-2-ene]-6'-ol

Chemical Property:

• Melting Point: 122-125°C
• PSA: 51.22000
• LogP: 3.33200
• Storage Temp.: Refrigerator
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 370.21440943
• Heavy Atom Count: 27
• Complexity: 798

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC#CC1(CCC2C1(CC=C3C2CCC45C3(O4)CCC6(C5)OCCO6)C)O
• Isomeric SMILES: CC#C[C@@]1(CC[C@@H]2[C@@]1(CC=C3[C@H]2CC[C@@]45[C@@]3(O4)CCC6(C5)OCCO6)C)O
• Uses: Intermediate in the preparation of Mifepristone derivatives.

Technology Process of (1'R,5'S,6'S,9'S,10'S,13'R)-5'-Methyl-6'-prop-1-ynylspiro[1,3-dioxolane-2,15'-18-oxapentacyclo[11.4.1.01,13.02,10.05,9]octadec-2-ene]-6'-ol

There total 7 articles about (1'R,5'S,6'S,9'S,10'S,13'R)-5'-Methyl-6'-prop-1-ynylspiro[1,3-dioxolane-2,15'-18-oxapentacyclo[11.4.1.01,13.02,10.05,9]octadec-2-ene]-6'-ol 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: 100.0%

1-propynylmagnesium bromide (16466-97-0,13254-27-8) + (5'R,10'R,13'S)-13'-methyl-1',2',6',7',8',12',13',14',15',16'-decahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one (39931-88-9,116003-08-8,39931-87-8) → (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3)

Guidance literature:

1-propynylmagnesium bromide; (5'R,10'R,13'S)-13'-methyl-1',2',6',7',8',12',13',14',15',16'-decahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one; In tetrahydrofuran; at 0 ℃; for 2h;

With ammonium chloride; In water;

Reference yield: 35.0%

(8S,13S,14S,17S)-13-methyl-17-(prop-1-yn-1-yl)-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol (84371-69-7) → (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1016/j.bmcl.2006.10.003

Reference yield: 29.0%

(5'R,10'R,13'S,16'R)-13',16'-dimethyl-1',2',6',7',8',12',13',14',15'-nonahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one (639520-94-8) + 1-propynylmagnesium bromide (16466-97-0,13254-27-8) → (5'R,8'S,10'R,13'S,14'S,17'S)-13'-methyl-17'-(prop-1-yn-1-yl)-1',2',7',8',12',13',14',15',16',17'-decahydro-4'H,6'H-spiro[[1,3]dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-ol (84371-57-3)

Guidance literature:

(5'R,10'R,13'S,16'R)-13',16'-dimethyl-1',2',6',7',8',12',13',14',15'-nonahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one; 1-propynylmagnesium bromide; In tetrahydrofuran; at 0 ℃; for 2.5h;

With ammonium chloride; In tetrahydrofuran; water;

upstream raw materials:

1-propynyl lithium

(5'R,10'R,13'S)-13'-methyl-1',2',6',7',8',12',13',14',15',16'-decahydro-17'H-spiro[1,3-dioxolane-2,3'-[5,10]epoxycyclopenta[a]phenanthren]-17'-one

(8S,13S,14S,17S)-13-methyl-17-(prop-1-yn-1-yl)-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol

ethylene deltenone

Downstream raw materials:

tert-butyl 4-((5R,11R,13S,17S)-5,17-dihydroxy-13-methyl-17-prop-1-ynyl-1,2,4,5,6,7,8,11,12,13,14,15,16,17-tetradecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-11-yl)phenyl(methyl)carbamate

(8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-11-(4-phenoxyphenyl)-17-(prop-1-yn-1-yl)-6,7,8,11,12,13,14,15,16,17-decahydro-7H-cyclopenta[a]phenanthrone-3(2H)-one