2-{[(2R,3R)-3-(benzyloxy)-tetrahydro-2H-pyran-2-yl]methoxy}ethyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: 2-{[(2R,3R)-3-(benzyloxy)-tetrahydro-2H-pyran-2-yl]methoxy}ethyl 4-methylbenzenesulfonate
• CAS No.: 864719-83-5
• Molecular Formula: C₂₂H₂₈O₆S
• Molecular Weight: 420.527
• Mol file: 864719-83-5.mol

Synonyms:2-{[(2R,3R)-3-(benzyloxy)-tetrahydro-2H-pyran-2-yl]methoxy}ethyl 4-methylbenzenesulfonate

Chemical Property of 2-{[(2R,3R)-3-(benzyloxy)-tetrahydro-2H-pyran-2-yl]methoxy}ethyl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{[(2R,3R)-3-(benzyloxy)-tetrahydro-2H-pyran-2-yl]methoxy}ethyl 4-methylbenzenesulfonate

There total 5 articles about 2-{[(2R,3R)-3-(benzyloxy)-tetrahydro-2H-pyran-2-yl]methoxy}ethyl 4-methylbenzenesulfonate 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: 90.0%

2-((2R,3R)-3-Benzyloxy-tetrahydro-pyran-2-ylmethoxy)-ethanol + p-toluenesulfonyl chloride (98-59-9) → 2-{[(2R,3R)-3-(benzyloxy)-tetrahydro-2H-pyran-2-yl]methoxy}ethyl 4-methylbenzenesulfonate (864719-83-5)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; at 20 ℃; for 7h;

DOI:10.1016/j.tet.2005.06.034

Reference yield:

(4aR,8aR)-2-Phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine → 2-{[(2R,3R)-3-(benzyloxy)-tetrahydro-2H-pyran-2-yl]methoxy}ethyl 4-methylbenzenesulfonate (864719-83-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 3.03 g / DIBAL-H / CH₂Cl₂; hexane / 0.5 h / 0 °C

2: 92 percent / tetrabutylammonium hydrogen sulphate; aq. NaOH / 24 h / 65 °C

3: 99 percent / aq. HCl / methanol / 1 h / 20 °C

4: 90 percent / aq. KOH / tetrahydrofuran / 7 h / 20 °C

With hydrogenchloride; potassium hydroxide; sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; diisobutylaluminium hydride; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1016/j.tet.2005.06.034

Reference yield:

[(2R,3R)-3-(phenylmethoxy)-tetrahydro-2H-pyran-2-yl]methan-1-ol (864719-80-2) → 2-{[(2R,3R)-3-(benzyloxy)-tetrahydro-2H-pyran-2-yl]methoxy}ethyl 4-methylbenzenesulfonate (864719-83-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / tetrabutylammonium hydrogen sulphate; aq. NaOH / 24 h / 65 °C

2: 99 percent / aq. HCl / methanol / 1 h / 20 °C

3: 90 percent / aq. KOH / tetrahydrofuran / 7 h / 20 °C

With hydrogenchloride; potassium hydroxide; sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran; methanol;

DOI:10.1016/j.tet.2005.06.034

upstream raw materials:

p-toluenesulfonyl chloride

[(2R,3R)-3-(phenylmethoxy)-tetrahydro-2H-pyran-2-yl]methan-1-ol

[2-(tetrahydro-2H-pyran-2-yloxy)ethoxy][(2R,3R)-3-(phenylmethoxy)(tetrahydro-2H-pyran-2-yl)]methane

benzaldehyde dimethyl acetal

Downstream raw materials:

2-{[(2R,3R)-3-(2-{[(2R,3R)-3-(phenylmethoxy)(tetrahydro-2H-pyran-2-yl)]methoxy}ethoxy)-tetrahydro-2H-pyran-2-yl]methoxy}ethyl 4-methylbenzenesulfonate

2-[((2R,3R)-3-{2-[((2R,3R)-3-hydroxy(tetrahydro-2H-pyran-2-yl))methoxy]ethoxy}-tetrahydro-2H-pyran-2-yl)methoxy]ethyl 4-methylbenzenesulfonate

2-{[(2R,3R)-3-(2-{[(2R,3R)-3-(benzyloxy)-tetrahydro-2H-pyran-2-yl]methoxy}ethoxy)-tetrahydro-2H-pyran-2-yl]methoxy}ethanol