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

Base Information

• Chemical Name: (2R,3R,4S,5R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3,5,6-hexanetriol
• CAS No.: 209251-09-2
• Molecular Formula: C₂₄H₃₆O₄Si
• Molecular Weight: 416.633
• Mol file: 209251-09-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (2R,3R,4S,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,4S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-pentan-3-ol → (2R,3R,4S,5R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3,5,6-hexanetriol (209251-09-2)

Guidance literature:

With water; acetic acid; at 23 ℃;

DOI:10.1016/S0040-4039(00)61370-9

Reference yield:

(2S,4'R)-(+)-2-(2,2-Dimethyl-1,3-dioxolan-4-yl)-1-propanol (71565-21-4) → (2R,3R,4S,5R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3,5,6-hexanetriol (209251-09-2)

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: 387 mg / CH₂Cl₂ / 0.67 h / 0 °C

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

3.2: 89 percent / tetrahydrofuran; hexane / 0.67 h / -78 - 20 °C

4.1: 70 percent / quinoline; H₂ / Lindlar catalyst / hexane / 0.25 h / 20 °C

5.1: 98 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1.17 h / -78 °C

6.1: 49 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 4 h / -10 - 0 °C

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

7.2: 62 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; copper(l) iodide; n-butyllithium; oxalyl dichloride; hydrogen; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; 1.1: Swern oxidation;

DOI:10.1016/j.tet.2007.02.011

Reference yield:

(2R)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]propanal (77398-87-9) → (2R,3R,4S,5R)-1-[(tert-butyldiphenylsilyl)oxy]-2,4-dimethyl-3,5,6-hexanetriol (209251-09-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Ph₃P / CH₂Cl₂ / 1 h / 0 °C

1.2: 387 mg / CH₂Cl₂ / 0.67 h / 0 °C

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

2.2: 89 percent / tetrahydrofuran; hexane / 0.67 h / -78 - 20 °C

3.1: 70 percent / quinoline; H₂ / Lindlar catalyst / hexane / 0.25 h / 20 °C

4.1: 98 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1.17 h / -78 °C

5.1: 49 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 4 h / -10 - 0 °C

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

6.2: 62 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; copper(l) iodide; n-butyllithium; hydrogen; diisobutylaluminium hydride; acetic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2007.02.011

upstream raw materials:

(3R,4R,5R)-3,5-dimethyl-6-[tert-butyldiphenylsilyloxy]-hex-1-en-4-ol

(2S,4'R)-(+)-2-(2,2-Dimethyl-1,3-dioxolan-4-yl)-1-propanol

{(2S,3R)-3-[(R)-1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-oxiranyl}-methanol

(2R,3S,4S)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2-methyl-pentane-1,3-diol