(2S,3R,5S,6S)-6-[(1S,2R,3S)-2-(3,4-Dimethoxy-benzyloxy)-1,3-dimethyl-pent-4-enyl]-3,5-dimethyl-tetrahydro-pyran-2-ol

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Chemical Name:(2S,3R,5S,6S)-6-[(1S,2R,3S)-2-(3,4-Dimethoxy-benzyloxy)-1,3-dimethyl-pent-4-enyl]-3,5-dimethyl-tetrahydro-pyran-2-ol
CAS No.:113956-91-5
Molecular Formula:C₂₃H₃₆O₅
Molecular Weight:392.536
Hs Code.:

Synonyms:(2S,3R,5S,6S)-6-[(1S,2R,3S)-2-(3,4-Dimethoxy-benzyloxy)-1,3-dimethyl-pent-4-enyl]-3,5-dimethyl-tetrahydro-pyran-2-ol

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Chemical Property of (2S,3R,5S,6S)-6-[(1S,2R,3S)-2-(3,4-Dimethoxy-benzyloxy)-1,3-dimethyl-pent-4-enyl]-3,5-dimethyl-tetrahydro-pyran-2-ol

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Technology Process of (2S,3R,5S,6S)-6-[(1S,2R,3S)-2-(3,4-Dimethoxy-benzyloxy)-1,3-dimethyl-pent-4-enyl]-3,5-dimethyl-tetrahydro-pyran-2-ol

There total 4 articles about (2S,3R,5S,6S)-6-[(1S,2R,3S)-2-(3,4-Dimethoxy-benzyloxy)-1,3-dimethyl-pent-4-enyl]-3,5-dimethyl-tetrahydro-pyran-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: 87.0%

: 102851-97-8
(3S,4R,5S)-4-(3,4-dimethoxybenzyloxy)-5-<2(S)-isopropyloxy-3(R),5(S)-dimethyl-6(S)-tetrahydroxypyranyl>-3-methylhexane

: 113956-91-5
(2S,3R,5S,6S)-6-[(1S,2R,3S)-2-(3,4-Dimethoxy-benzyloxy)-1,3-dimethyl-pent-4-enyl]-3,5-dimethyl-tetrahydro-pyran-2-ol

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; at 50 ℃; for 12h;
DOI:10.1248/cpb.35.2228

Reference yield:

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

: 113956-91-5
(2S,3R,5S,6S)-6-[(1S,2R,3S)-2-(3,4-Dimethoxy-benzyloxy)-1,3-dimethyl-pent-4-enyl]-3,5-dimethyl-tetrahydro-pyran-2-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) oxalyl chloride/DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -70 deg C, 40 min; 2.) CH₂Cl₂, -70 deg C to room temp., 1 h

2: 94 percent / BF₃*Et₂O / CH₂Cl₂ / 0.42 h / -90 °C

3: 91 percent / KH/DMSO / 0.08 h

4: 87 percent / 1 N HCl / tetrahydrofuran / 12 h / 50 °C

With hydrogenchloride; oxalyl dichloride; boron trifluoride diethyl etherate; potassium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane;
DOI:10.1248/cpb.35.2228

Reference yield:

: 102851-95-6
(R)-2-((2S,3S,5R,6S)-6-Isopropoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-propionaldehyde

: 113956-91-5
(2S,3R,5S,6S)-6-[(1S,2R,3S)-2-(3,4-Dimethoxy-benzyloxy)-1,3-dimethyl-pent-4-enyl]-3,5-dimethyl-tetrahydro-pyran-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 94 percent / BF₃*Et₂O / CH₂Cl₂ / 0.42 h / -90 °C

2: 91 percent / KH/DMSO / 0.08 h

3: 87 percent / 1 N HCl / tetrahydrofuran / 12 h / 50 °C

With hydrogenchloride; boron trifluoride diethyl etherate; potassium hydride; dimethyl sulfoxide; In tetrahydrofuran; dichloromethane;
DOI:10.1248/cpb.35.2228