(2S,3S,5R)-2-(3-Benzyloxy-2-methyl-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

Base Information

Chemical Name:(2S,3S,5R)-2-(3-Benzyloxy-2-methyl-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol
CAS No.:338799-47-6
Molecular Formula:C₃₂H₄₂O₄Si
Molecular Weight:518.769
Hs Code.:

Synonyms:(2S,3S,5R)-2-(3-Benzyloxy-2-methyl-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

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Chemical Property of (2S,3S,5R)-2-(3-Benzyloxy-2-methyl-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

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Technology Process of (2S,3S,5R)-2-(3-Benzyloxy-2-methyl-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

There total 7 articles about (2S,3S,5R)-2-(3-Benzyloxy-2-methyl-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-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: 80.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 338799-32-9
(2S,3S,5R)-2-[(RS)-3-(1-benzyloxy-2-methyl)]propyl-3-hydroxy-5-(hydroxy)methyltetrahydrofuran

: 338799-47-6
(2S,3S,5R)-2-(3-Benzyloxy-2-methyl-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

Guidance literature:: With 1H-imidazole; dmap; In dichloromethane; for 8h;
DOI:10.5555/ol015570y

Reference yield:

: 100-39-0
benzyl bromide

: 338799-47-6
(2S,3S,5R)-2-(3-Benzyloxy-2-methyl-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran; various solvent(s) / 1 h / 0 - 20 °C

1.2: 90 percent / TBAI / tetrahydrofuran; various solvent(s) / 15 h / 20 °C

2.1: AD-mix α; CH3SO2NH2 / H2O; 2-methyl-propan-2-ol / 13 h / 0 °C

3.1: KHMDS; N-triisopropylsulfonylimidazole / tetrahydrofuran / 0 - 20 °C

3.2: 50 percent / KHMDS / tetrahydrofuran / 0 - 20 °C

4.1: 80 percent / imidazole; 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 8 h

With 1H-imidazole; dmap; AD-mix-α; methanesulfonamide; N-triisopropylsulfonylimidazole; potassium hexamethylsilazane; sodium hydride; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 2.1: Sharpless asymmetric dihydroxylation;
DOI:10.5555/ol015570y

Reference yield:

: 338799-45-4
(+/-)-(E)-2-methyl-4,7-octadien-1-ol

: 338799-47-6
(2S,3S,5R)-2-(3-Benzyloxy-2-methyl-propyl)-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran; various solvent(s) / 1 h / 0 - 20 °C

1.2: 90 percent / TBAI / tetrahydrofuran; various solvent(s) / 15 h / 20 °C

2.1: AD-mix α; CH3SO2NH2 / H2O; 2-methyl-propan-2-ol / 13 h / 0 °C

3.1: KHMDS; N-triisopropylsulfonylimidazole / tetrahydrofuran / 0 - 20 °C

3.2: 50 percent / KHMDS / tetrahydrofuran / 0 - 20 °C

4.1: 80 percent / imidazole; 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 8 h

With 1H-imidazole; dmap; AD-mix-α; methanesulfonamide; N-triisopropylsulfonylimidazole; potassium hexamethylsilazane; sodium hydride; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 2.1: Sharpless asymmetric dihydroxylation;
DOI:10.5555/ol015570y