(2R,3R,5S,6S)-6-<(2S)-1-benzyloxyprop-2-yl>-3,5-dimethyl-2-hydroxy-2-(prop-1-en-3-yl)tetrahydropyran

Base Information

Chemical Name:(2R,3R,5S,6S)-6-<(2S)-1-benzyloxyprop-2-yl>-3,5-dimethyl-2-hydroxy-2-(prop-1-en-3-yl)tetrahydropyran
CAS No.:172995-84-5
Molecular Formula:C₂₀H₃₀O₃
Molecular Weight:318.456
Hs Code.:

Synonyms:(2R,3R,5S,6S)-6-<(2S)-1-benzyloxyprop-2-yl>-3,5-dimethyl-2-hydroxy-2-(prop-1-en-3-yl)tetrahydropyran

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Chemical Property of (2R,3R,5S,6S)-6-<(2S)-1-benzyloxyprop-2-yl>-3,5-dimethyl-2-hydroxy-2-(prop-1-en-3-yl)tetrahydropyran

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Technology Process of (2R,3R,5S,6S)-6-<(2S)-1-benzyloxyprop-2-yl>-3,5-dimethyl-2-hydroxy-2-(prop-1-en-3-yl)tetrahydropyran

There total 5 articles about (2R,3R,5S,6S)-6-<(2S)-1-benzyloxyprop-2-yl>-3,5-dimethyl-2-hydroxy-2-(prop-1-en-3-yl)tetrahydropyran 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%

: 144606-47-3
(2R,4S,5S,6S)-7-benzyloxy-5-hydroxy-2,4,6-trimethylheptanoic acid δ-lactone

: 1730-25-2
allylmagnesium bromide

: 172995-84-5
(2R,3R,5S,6S)-6-<(2S)-1-benzyloxyprop-2-yl>-3,5-dimethyl-2-hydroxy-2-(prop-1-en-3-yl)tetrahydropyran

Guidance literature:: In diethyl ether; at -80 ℃; for 2h;
DOI:10.1016/0040-4020(95)00905-1

Reference yield:

: 90093-98-4
(2S,3R,5S,6S)-2-isopropyloxy-3,5-dimethyl-6-<1(S)-methyl-2-hydroxyethyl>tetrahydropyran

: 172995-84-5
(2R,3R,5S,6S)-6-<(2S)-1-benzyloxyprop-2-yl>-3,5-dimethyl-2-hydroxy-2-(prop-1-en-3-yl)tetrahydropyran

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, 17 h

2: 76 percent / 1N aq. H₂SO₄ / dioxane / 3.5 h / 50 °C

3: 92 percent / PCC, 3A molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

4: 90 percent / diethyl ether / 2 h / -80 °C

With 3 A molecular sieve; sulfuric acid; sodium hydride; pyridinium chlorochromate; In 1,4-dioxane; diethyl ether; dichloromethane;
DOI:10.1016/0040-4020(95)00905-1

Reference yield:

: 100-44-7
benzyl chloride

: 172995-84-5
(2R,3R,5S,6S)-6-<(2S)-1-benzyloxyprop-2-yl>-3,5-dimethyl-2-hydroxy-2-(prop-1-en-3-yl)tetrahydropyran

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) NaH / 1.) THF, RT, 1 h, 2.) THF, 17 h

2: 76 percent / 1N aq. H₂SO₄ / dioxane / 3.5 h / 50 °C

3: 92 percent / PCC, 3A molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

4: 90 percent / diethyl ether / 2 h / -80 °C

With 3 A molecular sieve; sulfuric acid; sodium hydride; pyridinium chlorochromate; In 1,4-dioxane; diethyl ether; dichloromethane;
DOI:10.1016/0040-4020(95)00905-1