(3S,4S,5R)-4-(Methoxymethoxy)-3,5-dimethyl-8-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-1-octanol

Base Information

Chemical Name:(3S,4S,5R)-4-(Methoxymethoxy)-3,5-dimethyl-8-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-1-octanol
CAS No.:165961-50-2
Molecular Formula:C₂₈H₄₄O₄Si
Molecular Weight:472.74
Hs Code.:

Synonyms:(3S,4S,5R)-4-(Methoxymethoxy)-3,5-dimethyl-8-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-1-octanol

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Chemical Property of (3S,4S,5R)-4-(Methoxymethoxy)-3,5-dimethyl-8-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-1-octanol

Chemical Property:

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Technology Process of (3S,4S,5R)-4-(Methoxymethoxy)-3,5-dimethyl-8-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-1-octanol

There total 8 articles about (3S,4S,5R)-4-(Methoxymethoxy)-3,5-dimethyl-8-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-1-octanol 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:

: Ethyl (4R)-5-(tetrahydropyran-2-yloxy)-4-methyl-2-pentenoate

: 165961-50-2
(3S,4S,5R)-4-(Methoxymethoxy)-3,5-dimethyl-8-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-1-octanol

Guidance literature:: Multi-step reaction with 8 steps

1: H₂ / 10percent Pd/C / ethyl acetate / 6 h / 25 °C

2: LiAlH₄ / diethyl ether / 0.5 h / 25 °C

3: 99 percent / imidazole / dimethylformamide / 18 h / 25 °C

4: 80 percent / p-TsOH*H₂O / methanol / 0.83 h / 25 °C

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) 25 deg C, 30 min

6: BF₃*Et₂O / CH₂Cl₂ / 1.) -86 deg C, 15 min; -86 to -70 deg C, 45 min, 2.) 0 deg C, 1 h

7: 100 percent / i-Pr₂NEt / CH₂Cl₂ / 18 h / 25 °C

8: 1.) 9-BBN, 2.) 3 N aq. NaOH, 31percent aq. H₂O₂ / 1.) THF, 25 deg C, 17 h, 2.) 25 deg C, 7 h

With 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo00121a026

Reference yield:

: 123595-52-8
(2R)-2-Methyl-5-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-1-pentanol

: 165961-50-2
(3S,4S,5R)-4-(Methoxymethoxy)-3,5-dimethyl-8-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-1-octanol

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) 25 deg C, 30 min

2: BF₃*Et₂O / CH₂Cl₂ / 1.) -86 deg C, 15 min; -86 to -70 deg C, 45 min, 2.) 0 deg C, 1 h

3: 100 percent / i-Pr₂NEt / CH₂Cl₂ / 18 h / 25 °C

4: 1.) 9-BBN, 2.) 3 N aq. NaOH, 31percent aq. H₂O₂ / 1.) THF, 25 deg C, 17 h, 2.) 25 deg C, 7 h

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; boron trifluoride diethyl etherate; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1021/jo00121a026

Reference yield:

: 152033-12-0
(4R)-5-(Tetrahydropyran-2-yloxy)-4-methyl-1-pentanol

: 165961-50-2
(3S,4S,5R)-4-(Methoxymethoxy)-3,5-dimethyl-8-<<(1,1-dimethylethyl)diphenylsilyl>oxy>-1-octanol

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / imidazole / dimethylformamide / 18 h / 25 °C

2: 80 percent / p-TsOH*H₂O / methanol / 0.83 h / 25 °C

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) 25 deg C, 30 min

4: BF₃*Et₂O / CH₂Cl₂ / 1.) -86 deg C, 15 min; -86 to -70 deg C, 45 min, 2.) 0 deg C, 1 h

5: 100 percent / i-Pr₂NEt / CH₂Cl₂ / 18 h / 25 °C

6: 1.) 9-BBN, 2.) 3 N aq. NaOH, 31percent aq. H₂O₂ / 1.) THF, 25 deg C, 17 h, 2.) 25 deg C, 7 h

With 1H-imidazole; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; boron trifluoride diethyl etherate; dihydrogen peroxide; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00121a026