[(2R,4aR,6S,7R,8aS)-6-Methoxy-2-phenyl-7-prop-2-ynyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8E)-ylidene]-acetaldehyde

Base Information

Chemical Name:[(2R,4aR,6S,7R,8aS)-6-Methoxy-2-phenyl-7-prop-2-ynyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8E)-ylidene]-acetaldehyde
CAS No.:122592-26-1
Molecular Formula:C₁₉H₂₀O₅
Molecular Weight:328.365
Hs Code.:

Synonyms:[(2R,4aR,6S,7R,8aS)-6-Methoxy-2-phenyl-7-prop-2-ynyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8E)-ylidene]-acetaldehyde

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Chemical Property of [(2R,4aR,6S,7R,8aS)-6-Methoxy-2-phenyl-7-prop-2-ynyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8E)-ylidene]-acetaldehyde

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Technology Process of [(2R,4aR,6S,7R,8aS)-6-Methoxy-2-phenyl-7-prop-2-ynyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8E)-ylidene]-acetaldehyde

There total 4 articles about [(2R,4aR,6S,7R,8aS)-6-Methoxy-2-phenyl-7-prop-2-ynyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8E)-ylidene]-acetaldehyde 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: 90.0%

: 122592-07-8
2-[(2R,4aR,6S,7R,8aS)-6-Methoxy-2-phenyl-7-prop-2-ynyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8E)-ylidene]-ethanol

: 122592-26-1
[(2R,4aR,6S,7R,8aS)-6-Methoxy-2-phenyl-7-prop-2-ynyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8E)-ylidene]-acetaldehyde

Guidance literature:: With florisil; Celite; sodium acetate; pyridinium chlorochromate; In dichloromethane; Ambient temperature;
DOI:10.1021/jo00283a034

Reference yield:

: 122674-58-2
methyl 4,6-O-benzylidene-2-deoxy-2-C-propynyl-α-D-ribo-hexopyranosid-3-ulose

: 122592-26-1
[(2R,4aR,6S,7R,8aS)-6-Methoxy-2-phenyl-7-prop-2-ynyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8E)-ylidene]-acetaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) NaH / 1.) THF, 0 deg C, 0.5 h, 2.) THF, RT

2: DIBAL / toluene

3: 90 percent / PCC, Celite, sodium acetate, Florisil / CH₂Cl₂ / Ambient temperature

With florisil; Celite; sodium acetate; sodium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; In dichloromethane; toluene;
DOI:10.1021/jo00283a034

Reference yield:

: 194149-26-3
methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside

: 122592-26-1
[(2R,4aR,6S,7R,8aS)-6-Methoxy-2-phenyl-7-prop-2-ynyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8E)-ylidene]-acetaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) n-BuLi, 2.) hexamethylphosphoramide / 1.) THF, from -40 deg C to -30 deg C, 30 min, 2.) THF, from -35 deg C to -30 deg C

2: 1.) NaH / 1.) THF, 0 deg C, 0.5 h, 2.) THF, RT

3: DIBAL / toluene

4: 90 percent / PCC, Celite, sodium acetate, Florisil / CH₂Cl₂ / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; florisil; n-butyllithium; Celite; sodium acetate; sodium hydride; diisobutylaluminium hydride; pyridinium chlorochromate; In dichloromethane; toluene;
DOI:10.1021/jo00283a034