(4R,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-propyl]-tetrahydro-pyran-2,4-diol

Base Information

• Chemical Name: (4R,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-propyl]-tetrahydro-pyran-2,4-diol
• CAS No.: 130014-41-4
• Molecular Formula: C₂₄H₃₄O₄Si
• Molecular Weight: 414.617
• Mol file: 130014-41-4.mol

Synonyms:(4R,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-propyl]-tetrahydro-pyran-2,4-diol

Chemical Property of (4R,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-propyl]-tetrahydro-pyran-2,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-propyl]-tetrahydro-pyran-2,4-diol

There total 10 articles about (4R,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-propyl]-tetrahydro-pyran-2,4-diol 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: 99.0%

(2R,4R,6R,8R)-8-(t-butyldiphenylsiloxy)nonan-1,2,4,6-tetraol (129987-24-2) → (4R,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-propyl]-tetrahydro-pyran-2,4-diol (130014-41-4)

Guidance literature:

With sodium periodate; In methanol; water; for 0.333333h; Ambient temperature;

Reference yield:

1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-propan-2-one (120342-04-3) → (4R,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-propyl]-tetrahydro-pyran-2,4-diol (130014-41-4)

Guidance literature:

Multi-step reaction with 10 steps

1: LiI, LiAlH₄ / diethyl ether / 0.5 h / -78 °C

2: 92 percent / imidazole / dimethylformamide / 13 h / Ambient temperature

3: 77 percent / pyridinium toluene-p-sulphonate / methanol / 4 h / 50 °C

4: 89 percent / pyridine / 4.5 h / 0 °C

5: 97 percent / KH, MeOH / diethyl ether / 1 h / 0 °C

6: 1) BuLi / 1) THF, hexane, -30 deg C, 2 h, 2) THF, -20 deg C, 40 h

7: 68 percent / NBS, AgNO₃, 2,6-lutidine / acetonitrile; H₂O / 0.12 h

8: LiI, LiAlH₄ / diethyl ether / 0.5 h / -100 °C

9: 91 percent / pyridinium toluene-p-sulphonate / methanol / 4 h / 50 °C

10: 99 percent / NaIO₄ / methanol; H₂O / 0.33 h / Ambient temperature

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; methanol; sodium periodate; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; pyridinium p-toluenesulfonate; potassium hydride; silver nitrate; lithium iodide; In methanol; diethyl ether; water; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

(2R,4R)-4-(t-butyldiphenylsiloxy)-1,2-epoxypentane (130192-71-1) → (4R,6S)-6-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-propyl]-tetrahydro-pyran-2,4-diol (130014-41-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) BuLi / 1) THF, hexane, -30 deg C, 2 h, 2) THF, -20 deg C, 40 h

2: 68 percent / NBS, AgNO₃, 2,6-lutidine / acetonitrile; H₂O / 0.12 h

3: LiI, LiAlH₄ / diethyl ether / 0.5 h / -100 °C

4: 91 percent / pyridinium toluene-p-sulphonate / methanol / 4 h / 50 °C

5: 99 percent / NaIO₄ / methanol; H₂O / 0.33 h / Ambient temperature

With 2,6-dimethylpyridine; sodium periodate; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; pyridinium p-toluenesulfonate; silver nitrate; lithium iodide; In methanol; diethyl ether; water; acetonitrile;

upstream raw materials:

(2R,4R,6R,8R)-8-(t-butyldiphenylsiloxy)nonan-1,2,4,6-tetraol

1-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-propan-2-one

(2R,4R)-4-(t-butyldiphenylsiloxy)-1,2-epoxypentane

(2R,4R)-4-((tert-butyldiphenylsilyl)oxy)pentane-1,2-diol

Downstream raw materials:

(3R,5R,7R)-7-(t-butyldiphenylsiloxy)-3,5-dihydroxyoctanoic acid δ-lactone

(R)-1-methyl-2-[(S)-6-oxo-3,6-dihydro-2H-pyran-2-yl]ethyl 3-(3,4-dihydroxyphenyl)propanoate

(-)-<5(S),7(R)>-7-<5-(oct-2-enolide)-3',4'-bis-(t-butyldimethylsilyloxy)>-dihydrocinnamate

3-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionic acid (2R,4R)-2-((R)-2-{3-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionyloxy}-propyl)-6-oxo-tetrahydro-pyran-4-yl ester