(2R,3R,4S,5S,6S)-2,6-diallyl-4-(benzyloxy)-5-(4-methoxybenzyloxy)-tetrahydro-2H-pyran-3-ol

Base Information

• Chemical Name: (2R,3R,4S,5S,6S)-2,6-diallyl-4-(benzyloxy)-5-(4-methoxybenzyloxy)-tetrahydro-2H-pyran-3-ol
• CAS No.: 1093240-28-8
• Molecular Formula: C₂₆H₃₂O₅
• Molecular Weight: 424.537

Synonyms:(2R,3R,4S,5S,6S)-2,6-diallyl-4-(benzyloxy)-5-(4-methoxybenzyloxy)-tetrahydro-2H-pyran-3-ol

Chemical Property of (2R,3R,4S,5S,6S)-2,6-diallyl-4-(benzyloxy)-5-(4-methoxybenzyloxy)-tetrahydro-2H-pyran-3-ol

Chemical Property:

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Technology Process of (2R,3R,4S,5S,6S)-2,6-diallyl-4-(benzyloxy)-5-(4-methoxybenzyloxy)-tetrahydro-2H-pyran-3-ol

There total 1 articles about (2R,3R,4S,5S,6S)-2,6-diallyl-4-(benzyloxy)-5-(4-methoxybenzyloxy)-tetrahydro-2H-pyran-3-ol 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%

(2R,3R,4S,5S,6S)-6-allyl-4-(benzyloxy)-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)-tetrahydro-2H-pyran-3-ol (1093240-27-7) → (2R,3R,4S,5S,6S)-2,6-diallyl-4-(benzyloxy)-5-(4-methoxybenzyloxy)-tetrahydro-2H-pyran-3-ol (1093240-28-8)

Guidance literature:

With quinoline; Lindlar's catalyst; hydrogen; In ethyl acetate; for 2h; under 760.051 Torr;

DOI:10.1021/ol8025439

Reference yield: 98.0%

(2R,3R,4S,5S,6S)-2,6-diallyl-4-(benzyloxy)-5-(4-methoxybenzyloxy)-tetrahydro-2H-pyran-3-ol (1093240-28-8) + 5,5-dimethoxy-1-oxopentanoic acid (6719-33-1) → (2R,3R,4R,5S,6S)-2,6-diallyl-4-(benzyloxy)-5-(4-methoxybenzyloxy)-tetrahydro-2H-pyran-3-yl 5,5-dimethoxypentanoate (1093240-29-9)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ol8025439

Reference yield:

(2R,3R,4S,5S,6S)-2,6-diallyl-4-(benzyloxy)-5-(4-methoxybenzyloxy)-tetrahydro-2H-pyran-3-ol (1093240-28-8) + C42H47Cl3O8Si → (2R,3R,4R,5S,6S)-2,6-diallyl-4-(benzyloxy)-5-(4-methoxybenzyloxy)-tetrahydro-2H-pyran-3-yl 2-((2S,3S,4S,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-(tert-butyldimethylsilyloxy)-tetrahydro-2H-pyran-2-yl)acetate (1093240-42-6)

Guidance literature:

With dmap; In toluene; at 40 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ol8025439

upstream raw materials:

(2R,3R,4S,5S,6S)-6-allyl-4-(benzyloxy)-5-(4-methoxybenzyloxy)-2-(prop-2-ynyl)-tetrahydro-2H-pyran-3-ol

Downstream raw materials:

(2R,3R,4R,5S,6S)-2,6-diallyl-4-(benzyloxy)-5-(4-methoxybenzyloxy)-tetrahydro-2H-pyran-3-yl 2-((2S,3S,4S,5R,6R)-4,5-bis(benzyloxy)-6-(benzyloxymethyl)-3-(tert-butyldimethylsilyloxy)-tetrahydro-2H-pyran-2-yl)acetate

(2R,3R,4R,5S,6S)-2,6-diallyl-4-(benzyloxy)-5-(4-methoxybenzyloxy)-tetrahydro-2H-pyran-3-yl 5,5-dimethoxypentanoate

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