(2R,3R,4S,5R,6R)-6-Allyl-2-ethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3,4-diol

Base Information

• Chemical Name: (2R,3R,4S,5R,6R)-6-Allyl-2-ethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3,4-diol
• CAS No.: 867344-76-1
• Molecular Formula: C₁₈H₂₆O₅
• Molecular Weight: 322.401
• Mol file: 867344-76-1.mol

Synonyms:(2R,3R,4S,5R,6R)-6-Allyl-2-ethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3,4-diol

Chemical Property of (2R,3R,4S,5R,6R)-6-Allyl-2-ethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R,6R)-6-Allyl-2-ethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3,4-diol

There total 5 articles about (2R,3R,4S,5R,6R)-6-Allyl-2-ethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3,4-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:

[(3aS,4R,6R,7S,7aR)-6-Allyl-7-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-methanol (867344-64-7) → (2R,3R,4S,5R,6R)-6-Allyl-2-ethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3,4-diol (867344-76-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 °C

2: CuI / tetrahydrofuran; diethyl ether / 38 h / 4 °C

3: 100 percent / HCl / tetrahydrofuran; H₂O / 9 h / 22 °C

With 2,6-dimethylpyridine; hydrogenchloride; copper(l) iodide; In tetrahydrofuran; diethyl ether; dichloromethane; water;

DOI:10.1016/j.tetlet.2005.08.024

Reference yield:

Trifluoro-methanesulfonic acid (3aS,4R,6R,7S,7aR)-6-allyl-7-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester (867344-65-8) → (2R,3R,4S,5R,6R)-6-Allyl-2-ethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3,4-diol (867344-76-1)

Guidance literature:

Multi-step reaction with 2 steps

1: CuI / tetrahydrofuran; diethyl ether / 38 h / 4 °C

2: 100 percent / HCl / tetrahydrofuran; H₂O / 9 h / 22 °C

With hydrogenchloride; copper(l) iodide; In tetrahydrofuran; diethyl ether; water;

DOI:10.1016/j.tetlet.2005.08.024

Reference yield:

[(3aS,4R,6R,7S,7aR)-6-Allyl-7-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethoxy]-tert-butyl-diphenyl-silane (867344-63-6) → (2R,3R,4S,5R,6R)-6-Allyl-2-ethyl-5-(4-methoxy-benzyloxy)-tetrahydro-pyran-3,4-diol (867344-76-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / Bu₄NF / tetrahydrofuran / 3.5 h / 25 °C

2: 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 °C

3: CuI / tetrahydrofuran; diethyl ether / 38 h / 4 °C

4: 100 percent / HCl / tetrahydrofuran; H₂O / 9 h / 22 °C

With 2,6-dimethylpyridine; hydrogenchloride; copper(l) iodide; tetrabutyl ammonium fluoride; In tetrahydrofuran; diethyl ether; dichloromethane; water;

DOI:10.1016/j.tetlet.2005.08.024

upstream raw materials:

[(3aS,4R,6R,7S,7aR)-6-Allyl-7-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-methanol

Trifluoro-methanesulfonic acid (3aS,4R,6R,7S,7aR)-6-allyl-7-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester

[(3aS,4R,6R,7S,7aR)-6-Allyl-7-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethoxy]-tert-butyl-diphenyl-silane

p-Methoxybenzyl bromide

Downstream raw materials:

(2R,3R)-3-((R)-1-Hydroxymethyl-propoxy)-2-(4-methoxy-benzyloxy)-hex-5-en-1-ol