(1R)-1-[(2R,4S,5R)-4-allyl-5-methyl-2-phenyl-1,3-dioxan-5-yl]but-3-en-1-ol

Base Information

Chemical Name:(1R)-1-[(2R,4S,5R)-4-allyl-5-methyl-2-phenyl-1,3-dioxan-5-yl]but-3-en-1-ol
CAS No.:635727-02-5
Molecular Formula:C₁₈H₂₄O₃
Molecular Weight:288.387
Hs Code.:

Synonyms:(1R)-1-[(2R,4S,5R)-4-allyl-5-methyl-2-phenyl-1,3-dioxan-5-yl]but-3-en-1-ol

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Chemical Property of (1R)-1-[(2R,4S,5R)-4-allyl-5-methyl-2-phenyl-1,3-dioxan-5-yl]but-3-en-1-ol

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Technology Process of (1R)-1-[(2R,4S,5R)-4-allyl-5-methyl-2-phenyl-1,3-dioxan-5-yl]but-3-en-1-ol

There total 7 articles about (1R)-1-[(2R,4S,5R)-4-allyl-5-methyl-2-phenyl-1,3-dioxan-5-yl]but-3-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:

: 99493-25-1
diisopropyl 2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylate (tartrate allylboronate)

: (2R,4S,5S)-4-Allyl-5-methyl-2-phenyl-[1,3]dioxane-5-carbaldehyde

: 635727-02-5
(1R)-1-[(2R,4S,5R)-4-allyl-5-methyl-2-phenyl-1,3-dioxan-5-yl]but-3-en-1-ol

Guidance literature:: diisopropyl 2-allyl-1,3,2-dioxaborolane-4,5-dicarboxylate (tartrate allylboronate); (2R,4S,5S)-4-Allyl-5-methyl-2-phenyl-[1,3]dioxane-5-carbaldehyde; With 4 A molecular sieve; In toluene; at -78 - 20 ℃;

With sodium hydroxide; at 0 ℃;
DOI:10.1002/anie.200352016

Reference yield:

: 635727-00-3
{(2R,4S,5S)-4-allyl-5-methyl-2-phenyl-1,3-dioxan-5-yl}methanol

: 635727-02-5
(1R)-1-[(2R,4S,5R)-4-allyl-5-methyl-2-phenyl-1,3-dioxan-5-yl]but-3-en-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 - 0 °C

2: 4 Angstroem molecular sieves / toluene / 10 h / -78 - 20 °C

With oxalyl dichloride; 4 A molecular sieve; dimethyl sulfoxide; triethylamine; In dichloromethane; toluene; 1: Swern oxidation;
DOI:10.1055/s-2004-822340

Reference yield:

: 3663-46-5
5-hydroxymethyl-2,2,5-trimethyl-1,3-dioxane

: 635727-02-5
(1R)-1-[(2R,4S,5R)-4-allyl-5-methyl-2-phenyl-1,3-dioxan-5-yl]but-3-en-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: (COCl)2; dimethyl sulfoxide; Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: 4-Angstroem molecular sieves / toluene / -78 - 20 °C

2.2: aq. NaOH / 0 °C

3.1: trifluoroacetic acid / toluene / -20 - 0 °C

4.1: (COCl)2; dimethyl sulfoxide; Et₃N / CH₂Cl₂ / -78 - 0 °C

5.1: 4-Angstroem molecular sieves / toluene / -78 - 20 °C

5.2: aq. NaOH / 0 °C

With oxalyl dichloride; 4 A molecular sieve; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In dichloromethane; toluene; 1.1: Swern oxidation / 4.1: Swern oxidation;
DOI:10.1002/anie.200352016