(2S,3S,4S,5S)-4-Allyl-5-(4-methoxy-benzyloxy)-2-methoxymethoxy-2-methyl-decane-1,3-diol

Base Information

Chemical Name:(2S,3S,4S,5S)-4-Allyl-5-(4-methoxy-benzyloxy)-2-methoxymethoxy-2-methyl-decane-1,3-diol
CAS No.:327165-26-4
Molecular Formula:C₂₄H₄₀O₆
Molecular Weight:424.578
Hs Code.:

Synonyms:(2S,3S,4S,5S)-4-Allyl-5-(4-methoxy-benzyloxy)-2-methoxymethoxy-2-methyl-decane-1,3-diol

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Chemical Property of (2S,3S,4S,5S)-4-Allyl-5-(4-methoxy-benzyloxy)-2-methoxymethoxy-2-methyl-decane-1,3-diol

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Technology Process of (2S,3S,4S,5S)-4-Allyl-5-(4-methoxy-benzyloxy)-2-methoxymethoxy-2-methyl-decane-1,3-diol

There total 9 articles about (2S,3S,4S,5S)-4-Allyl-5-(4-methoxy-benzyloxy)-2-methoxymethoxy-2-methyl-decane-1,3-diol 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%

: 2-methoxymethoxy-propionic acid 2,6-di-tert-butyl-4-methyl-phenyl ester

: 327165-22-0
(2R,3S)-2-Allyl-3-(4-methoxy-benzyloxy)-octanal

: 327165-26-4
(2S,3S,4S,5S)-4-Allyl-5-(4-methoxy-benzyloxy)-2-methoxymethoxy-2-methyl-decane-1,3-diol

: 327165-27-5
(2R,3R,4S,5S)-4-Allyl-5-(4-methoxy-benzyloxy)-2-methoxymethoxy-2-methyl-decane-1,3-diol

Guidance literature:: 2-methoxymethoxy-propionic acid 2,6-di-tert-butyl-4-methyl-phenyl ester; With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

(2R,3S)-2-Allyl-3-(4-methoxy-benzyloxy)-octanal; In tetrahydrofuran;

With lithium aluminium tetrahydride; In tetrahydrofuran; at 23 ℃; Further stages.;
DOI:10.1021/ol0069610

Reference yield:

: 123-11-5
4-methoxy-benzaldehyde

: 327165-26-4
(2S,3S,4S,5S)-4-Allyl-5-(4-methoxy-benzyloxy)-2-methoxymethoxy-2-methyl-decane-1,3-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: PPTS / benzene / Heating

2.1: DIBAL-H / toluene / 23 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

4.1: LDA / tetrahydrofuran / -78 °C

4.2: tetrahydrofuran

4.3: 75 percent / LiAlH₄ / tetrahydrofuran / 23 °C

With oxalyl dichloride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene; benzene; 3.1: Swern oxidation;
DOI:10.1021/ol0069610

Reference yield:

: 66-25-1
hexanal

: 327165-26-4
(2S,3S,4S,5S)-4-Allyl-5-(4-methoxy-benzyloxy)-2-methoxymethoxy-2-methyl-decane-1,3-diol

Guidance literature:: Multi-step reaction with 7 steps

1.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 °C

2.1: Me₃Al / tetrahydrofuran; CH₂Cl₂ / 0 °C

3.1: LiAlH₄ / tetrahydrofuran / 23 °C

4.1: PPTS / benzene / Heating

5.1: DIBAL-H / toluene / 23 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

7.1: LDA / tetrahydrofuran / -78 °C

7.2: tetrahydrofuran

7.3: 75 percent / LiAlH₄ / tetrahydrofuran / 23 °C

With lithium aluminium tetrahydride; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; trimethylaluminum; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; toluene; benzene; 6.1: Swern oxidation;
DOI:10.1021/ol0069610