((2S,4S,5R,6S)-6-(2-(benzyloxy)ethyl)-4-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate

Base Information

• Chemical Name: ((2S,4S,5R,6S)-6-(2-(benzyloxy)ethyl)-4-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate
• CAS No.: 1350818-14-2
• Molecular Formula: C₂₃H₃₀O₆S
• Molecular Weight: 434.554

Synonyms:((2S,4S,5R,6S)-6-(2-(benzyloxy)ethyl)-4-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate

Chemical Property of ((2S,4S,5R,6S)-6-(2-(benzyloxy)ethyl)-4-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

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Technology Process of ((2S,4S,5R,6S)-6-(2-(benzyloxy)ethyl)-4-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate

There total 4 articles about ((2S,4S,5R,6S)-6-(2-(benzyloxy)ethyl)-4-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)methyl-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: 95.0%

(2S,3R,4S,6S)-2-(2-(benzyloxy)ethyl)-6-(hydroxymethyl)-3-methyltetrahydro-2H-pyran-4-ol (1350818-12-0) + p-toluenesulfonyl chloride (98-59-9) → ((2S,4S,5R,6S)-6-(2-(benzyloxy)ethyl)-4-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate (1350818-14-2)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 25 ℃; for 3h;

DOI:10.1016/j.tetlet.2014.11.097

Reference yield:

C6H12O2 (955044-11-8) → ((2S,4S,5R,6S)-6-(2-(benzyloxy)ethyl)-4-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate (1350818-14-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C

1.2: 2 h / 20 °C

2.1: triethylamine / dichloromethane / 8 h / 0 - 20 °C

With triethylamine; trifluoroacetic acid; In dichloromethane; 1.1: Prins reaction;

DOI:10.1016/j.tetlet.2011.09.134

Reference yield:

3-Benzyloxypropanal (19790-60-4) → ((2S,4S,5R,6S)-6-(2-(benzyloxy)ethyl)-4-hydroxy-5-methyltetrahydro-2H-pyran-2-yl)methyl-4-methylbenzenesulfonate (1350818-14-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trifluoroacetic acid / dichloromethane / 4 h / 0 - 20 °C

1.2: 2 h / 20 °C

2.1: triethylamine / dichloromethane / 8 h / 0 - 20 °C

With triethylamine; trifluoroacetic acid; In dichloromethane; 1.1: Prins reaction;

DOI:10.1016/j.tetlet.2011.09.134

upstream raw materials:

C₆H₁₂O₂

(2S,3R,4S,6S)-2-(2-(benzyloxy)ethyl)-6-(hydroxymethyl)-3-methyltetrahydro-2H-pyran-4-ol

p-toluenesulfonyl chloride

3-Benzyloxypropanal

Downstream raw materials:

(2S,3S)-2-[(4R,5R)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]hex-5-en-3-ol

C₁₈H₂₇IO₄

C₁₈H₂₆O₄

C₂₄H₃₂O₆

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