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

Base Information

• Chemical Name: (2S,3R,4S,5R,6R)-2,3-diallyl-4,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-3-ol
• CAS No.: 1152333-89-5
• Molecular Formula: C₃₃H₃₈O₅
• Molecular Weight: 514.662

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

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

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

There total 1 articles about (2S,3R,4S,5R,6R)-2,3-diallyl-4,5-bis(benzyloxy)-6-(benzyloxymethyl)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: 60.0%

allyl bromide (106-95-6) + 3-C-(3,4,6-tri-O-benzyl-β-D-arabino-hex-2-ulopyranosyl)propene (192929-31-0) → (2S,3S,4S,5R,6R)-2,3-diallyl-4,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-3-ol (1152333-90-8) + (2S,3R,4S,5R,6R)-2,3-diallyl-4,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-3-ol (1152333-89-5)

Guidance literature:

allyl bromide; With iodine; magnesium; In tetrahydrofuran; at 0 - 20 ℃;

3-C-(3,4,6-tri-O-benzyl-β-D-arabino-hex-2-ulopyranosyl)propene; In tetrahydrofuran; at -78 ℃; for 1h; optical yield given as %de;

DOI:10.1016/j.carres.2009.01.017

Reference yield: 89.0%

(2S,3R,4S,5R,6R)-2,3-diallyl-4,5-bis(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-3-ol (1152333-89-5) → (2R,3R,4S,4aR,8aS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4,4a,5,8,8a-hexahydro-2H-chromen-4a-ol (1152333-91-9)

Guidance literature:

With Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1016/j.carres.2009.01.017

upstream raw materials:

allyl bromide

3-C-(3,4,6-tri-O-benzyl-β-D-arabino-hex-2-ulopyranosyl)propene

Downstream raw materials:

(2R,3R,4S,4aR,8aS)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4,4a,5,8,8a-hexahydro-2H-chromen-4a-ol

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