(1S,2R,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(2-methoxycarbonyl-ethyl)-1-methyl-cyclohexanecarboxylic acid methyl ester

Base Information

Chemical Name:(1S,2R,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(2-methoxycarbonyl-ethyl)-1-methyl-cyclohexanecarboxylic acid methyl ester
CAS No.:312584-32-0
Molecular Formula:C₂₉H₄₀O₅Si
Molecular Weight:496.719
Hs Code.:

Synonyms:(1S,2R,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(2-methoxycarbonyl-ethyl)-1-methyl-cyclohexanecarboxylic acid methyl ester

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Chemical Property of (1S,2R,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(2-methoxycarbonyl-ethyl)-1-methyl-cyclohexanecarboxylic acid methyl ester

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Technology Process of (1S,2R,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(2-methoxycarbonyl-ethyl)-1-methyl-cyclohexanecarboxylic acid methyl ester

There total 13 articles about (1S,2R,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(2-methoxycarbonyl-ethyl)-1-methyl-cyclohexanecarboxylic acid methyl ester 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: 85.0%

: 67-56-1
methanol

: 312584-26-2
(1S,2R,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-2-(3-oxo-propyl)-cyclohexanecarboxylic acid methyl ester

: 312584-32-0
(1S,2R,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(2-methoxycarbonyl-ethyl)-1-methyl-cyclohexanecarboxylic acid methyl ester

Guidance literature:: With ozone; In dichloromethane; at -78 ℃;
DOI:10.1002/1099-0690(200010)2000:20<3427::aid-ejoc3427>3.3.co;2-o

Reference yield:

: 145632-33-3
(S)-7a′-methyl-2′,3′,7′,7a′-tetrahydrospiro[[1,3]dithiolane-2,5′-inden]-1′(6′H)-one

: 312584-32-0
(1S,2R,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(2-methoxycarbonyl-ethyl)-1-methyl-cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: 5.33 g / p-TsOH / toluene / 12 h / Heating; Dean-Stark apparatus

2.1: Na; liq. NH₃ / 1 h

3.1: BH₃*THF / 15 h / 0 - 20 °C

3.2: 83 percent / NaOH (3N); H₂O₂ (30 percent) / tetrahydrofuran / 4 h

4.1: 96 percent / mol. sieves; NMO; TPAP / CH₂Cl₂ / 3 h / 20 °C

5.1: 85 percent / NaOMe / methanol / 24 h / 20 °C

6.1: Li; liq. NH₃ / methanol / 2 h / -78 °C

7.1: p-TsOH; H₂O; Me₂CO / 10 h / 20 °C

8.1: 98 percent / imidazole / dimethylformamide / 48 h / 20 °C

9.1: Et₃N; NaI / acetonitrile / 12 h / 20 °C

10.1: mCPBA (70 percent) / pentane / 0.42 h / 0 °C

10.2: HCl (12N) / methanol / 0.08 h / 0 °C

11.1: Pb(OAc)4 / CH₂Cl₂ / 0.5 h / 0 °C

12.1: 85 percent / ozone / CH₂Cl₂ / -78 °C

With 1H-imidazole; lead(IV) acetate; N-methyl-2-indolinone; molecular sieve; tetrapropylammonium perruthennate; borane-THF; ammonia; water; sodium methylate; sodium; lithium; toluene-4-sulfonic acid; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid; acetone; sodium iodide; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; pentane; 1.1: Etherification / 2.1: Reduction / 3.1: Addition / 3.2: Oxidation / 4.1: Oxidation / 5.1: Isomerization / 6.1: Reduction / 7.1: Hydrolysis / 8.1: Substitution / 9.1: Substitution / 10.1: Oxidation / 10.2: Hydrolysis / 11.1: Ring cleavage / 12.1: Oxidation;
DOI:10.1002/1099-0690(200010)2000:20<3427::aid-ejoc3427>3.3.co;2-o

Reference yield:

: 312584-15-9
(8aS)-(1,1-ethylenedioxy)-8a-methyl-1,2,3,4,6,7,8,8a-octahydronaphthalene

: 312584-32-0
(1S,2R,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(2-methoxycarbonyl-ethyl)-1-methyl-cyclohexanecarboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: BH₃*THF / 15 h / 0 - 20 °C

1.2: 83 percent / NaOH (3N); H₂O₂ (30 percent) / tetrahydrofuran / 4 h

2.1: 96 percent / mol. sieves; NMO; TPAP / CH₂Cl₂ / 3 h / 20 °C

3.1: 85 percent / NaOMe / methanol / 24 h / 20 °C

4.1: Li; liq. NH₃ / methanol / 2 h / -78 °C

5.1: p-TsOH; H₂O; Me₂CO / 10 h / 20 °C

6.1: 98 percent / imidazole / dimethylformamide / 48 h / 20 °C

7.1: Et₃N; NaI / acetonitrile / 12 h / 20 °C

8.1: mCPBA (70 percent) / pentane / 0.42 h / 0 °C

8.2: HCl (12N) / methanol / 0.08 h / 0 °C

9.1: Pb(OAc)4 / CH₂Cl₂ / 0.5 h / 0 °C

10.1: 85 percent / ozone / CH₂Cl₂ / -78 °C

With 1H-imidazole; lead(IV) acetate; N-methyl-2-indolinone; molecular sieve; tetrapropylammonium perruthennate; borane-THF; ammonia; water; sodium methylate; lithium; toluene-4-sulfonic acid; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid; acetone; sodium iodide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; pentane; 1.1: Addition / 1.2: Oxidation / 2.1: Oxidation / 3.1: Isomerization / 4.1: Reduction / 5.1: Hydrolysis / 6.1: Substitution / 7.1: Substitution / 8.1: Oxidation / 8.2: Hydrolysis / 9.1: Ring cleavage / 10.1: Oxidation;
DOI:10.1002/1099-0690(200010)2000:20<3427::aid-ejoc3427>3.3.co;2-o