2-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-methoxymethoxy-7-methyl-chroman-2-yl}-propan-2-ol

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Chemical Name:2-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-methoxymethoxy-7-methyl-chroman-2-yl}-propan-2-ol
CAS No.:656240-47-0
Molecular Formula:C₃₃H₄₄O₅Si
Molecular Weight:548.795
Hs Code.:

Synonyms:2-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-methoxymethoxy-7-methyl-chroman-2-yl}-propan-2-ol

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Chemical Property of 2-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-methoxymethoxy-7-methyl-chroman-2-yl}-propan-2-ol

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Technology Process of 2-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-methoxymethoxy-7-methyl-chroman-2-yl}-propan-2-ol

There total 14 articles about 2-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-methoxymethoxy-7-methyl-chroman-2-yl}-propan-2-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: 49.0%

: 656240-46-9
(3R,5S)-5-(2-Bromo-5-methoxymethoxy-4-methyl-phenyl)-7-(tert-butyl-diphenyl-silanyloxy)-2-methyl-heptane-2,3-diol

: 7-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-5-(3-methoxymethoxy-4-methyl-phenyl)-2-methyl-heptan-3-one

: 656240-47-0
2-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-methoxymethoxy-7-methyl-chroman-2-yl}-propan-2-ol

Guidance literature:: With (Ra)-(2'-methoxy-[1,1']-binaphthalenyl-2-yl)-diphenylphosphine; caesium carbonate; palladium diacetate; In toluene; at 90 ℃; for 21h;
DOI:10.1055/s-2003-42097

Reference yield:

: 656240-38-9
3-(3-methoxymethoxy-4-methyl-phenyl)-pentane-1,5-diol

: 656240-47-0
2-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-methoxymethoxy-7-methyl-chroman-2-yl}-propan-2-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 53 percent / lipase AK / benzene / 17 h / 25 °C

2: 100 percent / imidazole; 4-DMAP / CH₂Cl₂ / 0.33 h / 25 °C

3: 100 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / 25 °C

4: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 25 °C

5: 76 percent / t-BuOK / tetrahydrofuran / 1 h / 25 °C

6: 79 percent / AD-mix-β; aq. MeSO2NH2 / 2-methyl-propan-2-ol / 45 h / 0 °C

7: 85 percent / NBS / dimethylformamide / 2 h / 25 °C

8: 49 percent / Cs₂CO₃; (R)-(+)-2-(diphenylphosphino)-2'-methoxy-1,1'-binaphthyl / Pd(OAc)2 / toluene / 21 h / 90 °C

With (Ra)-(2'-methoxy-[1,1']-binaphthalenyl-2-yl)-diphenylphosphine; 1H-imidazole; dmap; N-Bromosuccinimide; lithium aluminium tetrahydride; lipase AK; methanesulfonamide; AD-mix-β; potassium tert-butylate; caesium carbonate; Dess-Martin periodane; palladium diacetate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene; 5: Wittig olefination;
DOI:10.1055/s-2003-42097

Reference yield:

: 183803-06-7
3-hydroxy-4-methyliodobenzene

: 656240-47-0
2-{(2R,4S)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-methoxymethoxy-7-methyl-chroman-2-yl}-propan-2-ol

Guidance literature:: Multi-step reaction with 14 steps

1.1: 88 percent / NaH / dimethylformamide / 0.17 h / 25 °C

2.1: 97 percent / Et₃N; CuI / (PPh₃)2PdCl₂ / benzene / 1 h / 25 °C

3.1: 91 percent / LiAlH₄ / tetrahydrofuran / 1 h / 25 °C

4.1: 100 percent / Hg(OCOCF₃)2 / 19 h / Heating

5.1: 87 percent / i-Bu₃Al / CH₂Cl₂ / 0.5 h / 25 °C

6.1: BH₃*SMe₂ / tetrahydrofuran / 25 °C

6.2: 91 percent / aq. NaOH; H₂O₂ / 2 h / 25 °C

7.1: 53 percent / lipase AK / benzene / 17 h / 25 °C

8.1: 100 percent / imidazole; 4-DMAP / CH₂Cl₂ / 0.33 h / 25 °C

9.1: 100 percent / LiAlH₄ / tetrahydrofuran / 0.17 h / 25 °C

10.1: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h / 25 °C

11.1: 76 percent / t-BuOK / tetrahydrofuran / 1 h / 25 °C

12.1: 79 percent / AD-mix-β; aq. MeSO2NH2 / 2-methyl-propan-2-ol / 45 h / 0 °C

13.1: 85 percent / NBS / dimethylformamide / 2 h / 25 °C

14.1: 49 percent / Cs₂CO₃; (R)-(+)-2-(diphenylphosphino)-2'-methoxy-1,1'-binaphthyl / Pd(OAc)2 / toluene / 21 h / 90 °C

With (Ra)-(2'-methoxy-[1,1']-binaphthalenyl-2-yl)-diphenylphosphine; 1H-imidazole; dmap; N-Bromosuccinimide; copper(l) iodide; lithium aluminium tetrahydride; lipase AK; methanesulfonamide; dimethylsulfide borane complex; AD-mix-β; potassium tert-butylate; triisobutylaluminum; mercury(II) trifluoroacetate; sodium hydride; caesium carbonate; Dess-Martin periodane; triethylamine; bis-triphenylphosphine-palladium(II) chloride; palladium diacetate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; benzene; 2.1: Sonogashira coupling / 5.1: Claisen rearrangement / 11.1: Wittig olefination;
DOI:10.1055/s-2003-42097