2,3,3a,6,7,7a-Hexahydro-5',7a-diMethyl-4-hydroxy-indene-(1R)-1'-pentanoic Acid Methyl Ester 4-O-TrifluoroMethanesulfonate

Base Information

• Chemical Name: 2,3,3a,6,7,7a-Hexahydro-5',7a-diMethyl-4-hydroxy-indene-(1R)-1'-pentanoic Acid Methyl Ester 4-O-TrifluoroMethanesulfonate
• CAS No.: 145372-34-5
• Molecular Formula: C18H27F3O5S
• Molecular Weight: 412.471
• Mol file: 145372-34-5.mol

Synonyms:2,3,3a,6,7,7a-Hexahydro-5',7a-diMethyl-4-hydroxy-indene-(1R)-1'-pentanoic Acid Methyl Ester 4-O-TrifluoroMethanesulfonate;(δR,1R,3aR,7aR)-2,3,3a,6,7,7a-Hexahydro-δ,7a-diMethyl-4-[[(trifluoroMethyl)sulfonyl]oxy]-1H-indene-1-pentanoic Acid Methyl Ester

Chemical Property of 2,3,3a,6,7,7a-Hexahydro-5',7a-diMethyl-4-hydroxy-indene-(1R)-1'-pentanoic Acid Methyl Ester 4-O-TrifluoroMethanesulfonate

Chemical Property:

• PSA: 78.05000
• LogP: 5.62300

Purity/Quality:

95% ^*data from raw suppliers

2,3,3a,6,7,7a-Hexahydro-5’,7a-dimethyl-4-hydroxy-indene-(1R)-1’-pentanoicAcidMethylEster4-O-Trifluoromethanesulfonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate in the preparation of Dihydroxyvitamin D3 and associated metabolites.

Technology Process of 2,3,3a,6,7,7a-Hexahydro-5',7a-diMethyl-4-hydroxy-indene-(1R)-1'-pentanoic Acid Methyl Ester 4-O-TrifluoroMethanesulfonate

There total 4 articles about 2,3,3a,6,7,7a-Hexahydro-5',7a-diMethyl-4-hydroxy-indene-(1R)-1'-pentanoic Acid Methyl Ester 4-O-TrifluoroMethanesulfonate 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: 65.0%

des-A,B-22-iodo-23,24-dinorchol-8-enyl trifluoromethanesulfonate (145372-33-4) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → Trifluoro-methanesulfonic acid (1R,3aR,7aR)-1-isopropyl-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl ester + methyl-des-A,B-8-<(trifluoromethanesulfonyl)oxy>chol-8-ene-24-carboxylate (145372-34-5)

Guidance literature:

With copper(l) iodide; zinc; In ethanol; water; for 0.666667h; sonication;

DOI:10.1021/jo00053a023

Reference yield:

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol (64190-52-9) → methyl-des-A,B-8-<(trifluoromethanesulfonyl)oxy>chol-8-ene-24-carboxylate (145372-34-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / Ph₃P, imidazole, I₂ / tetrahydrofuran / -20 deg C, 15 min then RT, 1.5 h

2: 90 percent / PDC / CH₂Cl₂ / 6 h / Ambient temperature

3: 92 percent / LDA / tetrahydrofuran / 2 h / -78 °C

4: 65 percent / CuI, Zn / ethanol; H₂O / 0.67 h / sonication

With 1H-imidazole; copper(l) iodide; dipyridinium dichromate; iodine; triphenylphosphine; zinc; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; water;

DOI:10.1021/jo00053a023

Reference yield:

(1R,3aR,4S,7aR)-octahydro-1-[(S)-1-iodopropan-2-yl]-7a-methyl-1H-inden-4-ol (116535-65-0) → methyl-des-A,B-8-<(trifluoromethanesulfonyl)oxy>chol-8-ene-24-carboxylate (145372-34-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / PDC / CH₂Cl₂ / 6 h / Ambient temperature

2: 92 percent / LDA / tetrahydrofuran / 2 h / -78 °C

3: 65 percent / CuI, Zn / ethanol; H₂O / 0.67 h / sonication

With copper(l) iodide; dipyridinium dichromate; zinc; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; water;

DOI:10.1021/jo00053a023

upstream raw materials:

des-A,B-22-iodo-23,24-dinorchol-8-enyl trifluoromethanesulfonate

acrylic acid methyl ester

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol

(1R,3aR,4S,7aR)-octahydro-1-[(S)-1-iodopropan-2-yl]-7a-methyl-1H-inden-4-ol

Downstream raw materials:

1α-[(tert-butyldimethylsilyl)oxy]-24-(methoxycarbonyl)-25,26,27-trisnorvitamin D3 tert-butyldimethylsilyl ether

(1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol

calcitriol

1α-<(tert-butyldimethylsilyl)-oxy>-6,7-didehydro-24-(methoxycarbonyl)-25,26,27-trisnorprevitamin D₃ tert-butyldimethylsilyl ether