(2R,3S,4R,5R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3,5,6-hexanetriol

Base Information

Chemical Name:(2R,3S,4R,5R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3,5,6-hexanetriol
CAS No.:209251-15-0
Molecular Formula:C₂₄H₃₆O₄Si
Molecular Weight:416.633
Hs Code.:

Synonyms:(2R,3S,4R,5R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3,5,6-hexanetriol

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Chemical Property of (2R,3S,4R,5R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3,5,6-hexanetriol

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Technology Process of (2R,3S,4R,5R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3,5,6-hexanetriol

There total 10 articles about (2R,3S,4R,5R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3,5,6-hexanetriol 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:

: (2R,3S,4R)-1-(tert-Butyl-diphenyl-silanyloxy)-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-pentan-3-ol

: 209251-15-0
(2R,3S,4R,5R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3,5,6-hexanetriol

Guidance literature:: With water; acetic acid; at 23 ℃;
DOI:10.1016/S0040-4039(00)61370-9

Reference yield:

: 74243-89-3
*R^*)>-α,2,2-trimethyl-1,3-dioxolane-4-ethanol

: 209251-15-0
(2R,3S,4R,5R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3,5,6-hexanetriol

Guidance literature:: Multi-step reaction with 9 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.83 h / -78 - 20 °C

2.1: Ph₃P / CH₂Cl₂ / 1 h / 0 °C

2.2: 533 mg / CH₂Cl₂ / 0.67 h / 0 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

3.2: 70 percent / tetrahydrofuran; hexane / 0.67 h / -78 - 20 °C

4.1: 90 percent / quinoline; H₂ / Lindlar catalyst / hexane / 0.25 h / 20 °C

5.1: 88 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1.17 h / -78 °C

6.1: 35 percent / tert-butyl hydroperoxide; Ti(OiPr)4; (+)-diethyl tartrate / 4 Angstroem molecular sieves / CH₂Cl₂; toluene / 2 h / -23 °C

7.1: CuI / diethyl ether / 0.5 h / -23 °C

7.2: 68 percent / diethyl ether / 1.75 h / -40 - -23 °C

8.1: imidazole / dimethylformamide / 1 h / 0 °C

9.1: acetic acid / H₂O / 3.7 h / 20 °C

With 1H-imidazole; quinoline; titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; n-butyllithium; oxalyl dichloride; hydrogen; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; (+)-Weinsaeure-diethylester; triethylamine; triphenylphosphine; Lindlar's catalyst; 4 A molecular sieve; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Swern oxidation;
DOI:10.1016/j.tet.2007.02.011

Reference yield:

: 114925-44-9
*S^*)>-α,2,2-trimethyl-1,3-dioxolane-4-acetaldehyde

: 209251-15-0
(2R,3S,4R,5R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3,5,6-hexanetriol

Guidance literature:: Multi-step reaction with 8 steps

1.1: Ph₃P / CH₂Cl₂ / 1 h / 0 °C

1.2: 533 mg / CH₂Cl₂ / 0.67 h / 0 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C

2.2: 70 percent / tetrahydrofuran; hexane / 0.67 h / -78 - 20 °C

3.1: 90 percent / quinoline; H₂ / Lindlar catalyst / hexane / 0.25 h / 20 °C

4.1: 88 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1.17 h / -78 °C

5.1: 35 percent / tert-butyl hydroperoxide; Ti(OiPr)4; (+)-diethyl tartrate / 4 Angstroem molecular sieves / CH₂Cl₂; toluene / 2 h / -23 °C

6.1: CuI / diethyl ether / 0.5 h / -23 °C

6.2: 68 percent / diethyl ether / 1.75 h / -40 - -23 °C

7.1: imidazole / dimethylformamide / 1 h / 0 °C

8.1: acetic acid / H₂O / 3.7 h / 20 °C

With 1H-imidazole; quinoline; titanium(IV) isopropylate; tert.-butylhydroperoxide; copper(l) iodide; n-butyllithium; hydrogen; diisobutylaluminium hydride; acetic acid; (+)-Weinsaeure-diethylester; triphenylphosphine; Lindlar's catalyst; 4 A molecular sieve; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tet.2007.02.011