(2S,3S,4R,5R,6R)-2-Allyl-3,4-bis-benzyloxy-6-(3,3-dibromo-allyl)-5-(1-ethoxy-ethoxy)-tetrahydro-pyran

Base Information

Chemical Name:(2S,3S,4R,5R,6R)-2-Allyl-3,4-bis-benzyloxy-6-(3,3-dibromo-allyl)-5-(1-ethoxy-ethoxy)-tetrahydro-pyran
CAS No.:474832-12-7
Molecular Formula:C₂₉H₃₆Br₂O₅
Molecular Weight:624.41
Hs Code.:

Synonyms:(2S,3S,4R,5R,6R)-2-Allyl-3,4-bis-benzyloxy-6-(3,3-dibromo-allyl)-5-(1-ethoxy-ethoxy)-tetrahydro-pyran

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Chemical Property of (2S,3S,4R,5R,6R)-2-Allyl-3,4-bis-benzyloxy-6-(3,3-dibromo-allyl)-5-(1-ethoxy-ethoxy)-tetrahydro-pyran

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Technology Process of (2S,3S,4R,5R,6R)-2-Allyl-3,4-bis-benzyloxy-6-(3,3-dibromo-allyl)-5-(1-ethoxy-ethoxy)-tetrahydro-pyran

There total 1 articles about (2S,3S,4R,5R,6R)-2-Allyl-3,4-bis-benzyloxy-6-(3,3-dibromo-allyl)-5-(1-ethoxy-ethoxy)-tetrahydro-pyran 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: 82.0%

: 558-13-4
carbon tetrabromide

: 109-92-2,25104-37-4
ethyl vinyl ether

: [(2R,3R,4R,5S,6S)-6-Allyl-4,5-bis-benzyloxy-3-(1-ethoxy-ethoxy)-tetrahydro-pyran-2-yl]-acetaldehyde

: 474832-12-7
(2S,3S,4R,5R,6R)-2-Allyl-3,4-bis-benzyloxy-6-(3,3-dibromo-allyl)-5-(1-ethoxy-ethoxy)-tetrahydro-pyran

Guidance literature:: carbon tetrabromide; [(2R,3R,4R,5S,6S)-6-Allyl-4,5-bis-benzyloxy-3-(1-ethoxy-ethoxy)-tetrahydro-pyran-2-yl]-acetaldehyde; With triphenylphosphine; In dichloromethane; at 0 ℃; for 0.5h;

ethyl vinyl ether; With pyridinium p-toluenesulfonate; In dichloromethane; at 20 ℃; for 6h;
DOI:10.1016/S0040-4020(02)00659-2

Reference yield:

: 104-53-0
3-phenyl-propionaldehyde

: 474832-12-7
(2S,3S,4R,5R,6R)-2-Allyl-3,4-bis-benzyloxy-6-(3,3-dibromo-allyl)-5-(1-ethoxy-ethoxy)-tetrahydro-pyran

: 6-[(2R,3R,4R,5S,6S)-6-Allyl-4,5-bis-benzyloxy-3-(1-ethoxy-ethoxy)-tetrahydro-pyran-2-yl]-1-phenyl-hex-4-yn-3-ol

Guidance literature:: (2S,3S,4R,5R,6R)-2-Allyl-3,4-bis-benzyloxy-6-(3,3-dibromo-allyl)-5-(1-ethoxy-ethoxy)-tetrahydro-pyran; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h;

3-phenyl-propionaldehyde; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 1h;
DOI:10.1016/S0040-4020(02)00659-2

Reference yield:

: 474832-12-7
(2S,3S,4R,5R,6R)-2-Allyl-3,4-bis-benzyloxy-6-(3,3-dibromo-allyl)-5-(1-ethoxy-ethoxy)-tetrahydro-pyran

: (2R,3R,4S,5S,6S)-6-Allyl-4,5-bis-benzyloxy-2-(4-hydroxy-6-phenyl-hex-2-ynyl)-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / -78 °C

1.2: tetrahydrofuran; hexane / 1 h / -78 - 0 °C

2.1: 0.82 g / MeOH; Amberlyst-15E / 1.5 h / 20 °C

With methanol; n-butyllithium; Amberlyst-15E; In tetrahydrofuran; hexane;
DOI:10.1016/S0040-4020(02)00659-2