1-[(2R,4aR,6S,8aS)-6-Methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8Z)-ylidene]-propan-2-ol

Base Information

• Chemical Name: 1-[(2R,4aR,6S,8aS)-6-Methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8Z)-ylidene]-propan-2-ol
• CAS No.: 122592-24-9
• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.359

Synonyms:1-[(2R,4aR,6S,8aS)-6-Methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8Z)-ylidene]-propan-2-ol

Chemical Property of 1-[(2R,4aR,6S,8aS)-6-Methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8Z)-ylidene]-propan-2-ol

Chemical Property:

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Technology Process of 1-[(2R,4aR,6S,8aS)-6-Methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8Z)-ylidene]-propan-2-ol

There total 2 articles about 1-[(2R,4aR,6S,8aS)-6-Methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8Z)-ylidene]-propan-2-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:

1-[(2R,4aR,6S,8aS)-6-Methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8Z)-ylidene]-propan-2-one (122592-23-8) → 1-[(2R,4aR,6S,8aS)-6-Methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8Z)-ylidene]-propan-2-ol (122592-24-9)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; Yield given;

DOI:10.1021/jo00283a034

Reference yield:

methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose (63598-31-2) → 1-[(2R,4aR,6S,8aS)-6-Methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8Z)-ylidene]-propan-2-ol (122592-24-9)

Guidance literature:

Multi-step reaction with 2 steps

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

2: DIBAL / CH₂Cl₂

With sodium hydride; diisobutylaluminium hydride; In dichloromethane;

DOI:10.1021/jo00283a034

Reference yield: 60.0%

N,N-dimethylacetamide dimethyl acetal (18871-66-4) + 1-[(2R,4aR,6S,8aS)-6-Methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8Z)-ylidene]-propan-2-ol (122592-24-9) → methyl 4,6-O-benzylidene-2,3-dideoxy-3-C-((N,N-dimethylcarbamoyl)methyl)-3-C-((E)-1-propenyl)-α-D-ribo- and arabinopyranoside

Guidance literature:

With 4 A molecular sieve; In toluene; Heating;

DOI:10.1021/jo00283a034

upstream raw materials:

1-[(2R,4aR,6S,8aS)-6-Methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-(8Z)-ylidene]-propan-2-one

methyl 4,6-O-(R)-benzylidene-2-deoxy-α-D-erythrohexopyranosid-3-ulose

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