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

Base Information

• Chemical Name: (2R,4aR,6S,8aR)-6-Methoxy-2-phenyl-7-prop-(E)-ylidene-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one
• CAS No.: 114047-68-6
• Molecular Formula: C₁₇H₂₀O₅
• Molecular Weight: 304.343

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

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

Chemical Property:

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

There total 3 articles about (2R,4aR,6S,8aR)-6-Methoxy-2-phenyl-7-prop-(E)-ylidene-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one 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: 75.0%

(2R,4aR,6S,7R,8aR)-7-(1-Hydroxy-propyl)-6-methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one → (2R,4aR,6S,8aR)-6-Methoxy-2-phenyl-7-prop-(E)-ylidene-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one (114047-68-6)

Guidance literature:

With methanesulfonyl chloride; In pyridine; Ambient temperature;

DOI:10.1039/c39870000884

Reference yield:

methyl 2,3:4,6-di-O-benzylidene-α-D-mannopyranoside (194149-26-3) → (2R,4aR,6S,8aR)-6-Methoxy-2-phenyl-7-prop-(E)-ylidene-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one (114047-68-6)

Guidance literature:

Multi-step reaction with 3 steps

1: BuLi / tetrahydrofuran / -30 °C

2: -30 °C

3: 75 percent / methanesulphonyl chloride / pyridine / Ambient temperature

With n-butyllithium; methanesulfonyl chloride; In tetrahydrofuran; pyridine;

DOI:10.1039/c39870000884

Reference yield:

Lithium; (2R,4aR,6S,8aR)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-olate → (2R,4aR,6S,8aR)-6-Methoxy-2-phenyl-7-prop-(E)-ylidene-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-one (114047-68-6)

Guidance literature:

Multi-step reaction with 2 steps

1: -30 °C

2: 75 percent / methanesulphonyl chloride / pyridine / Ambient temperature

With methanesulfonyl chloride; In pyridine;

DOI:10.1039/c39870000884

upstream raw materials:

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

Downstream raw materials:

Bromomethyl-[(2R,4aR,6S,8S,8aR)-6-methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-dimethyl-silane

Bromomethyl-[(2R,4aR,6S,8R,8aR)-6-methoxy-2-phenyl-7-prop-(Z)-ylidene-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-dimethyl-silane

Chloro-acetic acid (R)-1-((2R,4aR,6S,8aS)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-propyl ester

Chloro-acetic acid (S)-1-((2R,4aR,6S,8aS)-6-methoxy-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-propyl ester

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