(Z)-(S)-4-((2R,4aR,6R,8aS)-7-Methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-pent-2-en-1-ol

Base Information

Chemical Name:(Z)-(S)-4-((2R,4aR,6R,8aS)-7-Methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-pent-2-en-1-ol
CAS No.:150019-03-7
Molecular Formula:C₁₉H₂₄O₄
Molecular Weight:316.397
Hs Code.:

Synonyms:(Z)-(S)-4-((2R,4aR,6R,8aS)-7-Methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-pent-2-en-1-ol

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Chemical Property of (Z)-(S)-4-((2R,4aR,6R,8aS)-7-Methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-pent-2-en-1-ol

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Technology Process of (Z)-(S)-4-((2R,4aR,6R,8aS)-7-Methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-pent-2-en-1-ol

There total 7 articles about (Z)-(S)-4-((2R,4aR,6R,8aS)-7-Methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-pent-2-en-1-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: 91.0%

: (Z)-(S)-4-((2R,4aR,6R,8aS)-7-Methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-pent-2-enoic acid methyl ester

: 150019-03-7
(Z)-(S)-4-((2R,4aR,6R,8aS)-7-Methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-pent-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride;
DOI:10.1021/ja00069a013

Reference yield:

: 150196-68-2
4,6-O-Benzyliden-1,2-didehydro-1,2-dideoxy-2-methyl-D-ribo-hexopyranose

: 150019-03-7
(Z)-(S)-4-((2R,4aR,6R,8aS)-7-Methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-pent-2-en-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 96 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

2: 1.) hexamethyldisilazane, n-BuLi, 2.) HMPA / 1.) THF, -100 deg C, 30 min, 2.) THF, from -100 deg C to RT, 90 min, 3.) benzene, reflux, 19 h

3: 2 N aq. NaOH / tetrahydrofuran / 3 h

4: 87 percent / LiAlH₄ / diethyl ether / 3 h / 0 °C

5: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, a) -78 deg C, 40 min, b) from -78 deg C to 0 deg C, 2 h

7: 91 percent / DIBAL

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja00069a013

Reference yield:

: 2-((2R,4aR,6R,8aS)-7-Methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-propionic acid

: 150019-03-7
(Z)-(S)-4-((2R,4aR,6R,8aS)-7-Methyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-pent-2-en-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 87 percent / LiAlH₄ / diethyl ether / 3 h / 0 °C

2: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) CH₂Cl₂, a) -78 deg C, 40 min, b) from -78 deg C to 0 deg C, 2 h

4: 91 percent / DIBAL

With lithium aluminium tetrahydride; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In diethyl ether;
DOI:10.1021/ja00069a013