(2R,3R)-1-(tert-butyldiphenylsilyloxy)-3-(tetrahydropyran-2-yloxymethyl)pentan-2-ol

Base Information

Chemical Name:(2R,3R)-1-(tert-butyldiphenylsilyloxy)-3-(tetrahydropyran-2-yloxymethyl)pentan-2-ol
CAS No.:442202-34-8
Molecular Formula:C₂₇H₄₀O₄Si
Molecular Weight:456.698
Hs Code.:

Synonyms:(2R,3R)-1-(tert-butyldiphenylsilyloxy)-3-(tetrahydropyran-2-yloxymethyl)pentan-2-ol

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Chemical Property of (2R,3R)-1-(tert-butyldiphenylsilyloxy)-3-(tetrahydropyran-2-yloxymethyl)pentan-2-ol

Chemical Property:

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Technology Process of (2R,3R)-1-(tert-butyldiphenylsilyloxy)-3-(tetrahydropyran-2-yloxymethyl)pentan-2-ol

There total 8 articles about (2R,3R)-1-(tert-butyldiphenylsilyloxy)-3-(tetrahydropyran-2-yloxymethyl)pentan-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: 98.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 442202-33-7
(2R,3R)-3-(tetrahydropyran-2-yloxymethyl)pentane-1,2-diol

: 442202-34-8
(2R,3R)-1-(tert-butyldiphenylsilyloxy)-3-(tetrahydropyran-2-yloxymethyl)pentan-2-ol

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 20h;
DOI:10.1021/ol025775m DOI:10.1016/j.tet.2004.05.039

Reference yield:

: 117935-51-0
(R)-1-O-acetyl-2-ethyl-1,3-propanediol

: 442202-34-8
(2R,3R)-1-(tert-butyldiphenylsilyloxy)-3-(tetrahydropyran-2-yloxymethyl)pentan-2-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: PPTS / CH₂Cl₂ / 2 h / 20 °C

2.1: K₂CO₃ / methanol / 3 h / 20 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

4.2: 695 mg / tetrahydrofuran; hexane / 1.5 h / 20 °C

5.1: 80 percent / (DHQD)2PYR; K₂OsO₄*2H₂O; K₃Fe(CN)6 / K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

6.1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 20 h / 20 °C

With dmap; potassium osmate(VI); n-butyllithium; oxalyl dichloride; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; pyridinium p-toluenesulfonate; potassium carbonate; dimethyl sulfoxide; triethylamine; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; methanol; hexane; dichloromethane; water; tert-butyl alcohol; 3.1: Swern oxidation / 4.2: Wittig reaction;
DOI:10.1016/j.tet.2004.05.039

Reference yield:

: (R)-2-(Tetrahydro-pyran-2-yloxymethyl)-butyraldehyde

: 442202-34-8
(2R,3R)-1-(tert-butyldiphenylsilyloxy)-3-(tetrahydropyran-2-yloxymethyl)pentan-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

1.2: 695 mg / tetrahydrofuran; hexane / 1.5 h / 20 °C

2.1: 80 percent / (DHQD)2PYR; K₂OsO₄*2H₂O; K₃Fe(CN)6 / K₂CO₃ / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

3.1: 98 percent / Et₃N; DMAP / CH₂Cl₂ / 20 h / 20 °C

With dmap; potassium osmate(VI); n-butyllithium; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; triethylamine; potassium hexacyanoferrate(III); potassium carbonate; In tetrahydrofuran; hexane; dichloromethane; water; tert-butyl alcohol; 1.2: Wittig reaction;
DOI:10.1016/j.tet.2004.05.039