2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-4-allyl-3-hydroxy-5-(4-methoxy-benzyloxy)-2-methoxymethoxy-2-methyl-decyl ester

Base Information

Chemical Name:2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-4-allyl-3-hydroxy-5-(4-methoxy-benzyloxy)-2-methoxymethoxy-2-methyl-decyl ester
CAS No.:327165-28-6
Molecular Formula:C₂₉H₄₈O₇
Molecular Weight:508.696
Hs Code.:

Synonyms:2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-4-allyl-3-hydroxy-5-(4-methoxy-benzyloxy)-2-methoxymethoxy-2-methyl-decyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-4-allyl-3-hydroxy-5-(4-methoxy-benzyloxy)-2-methoxymethoxy-2-methyl-decyl ester

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Technology Process of 2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-4-allyl-3-hydroxy-5-(4-methoxy-benzyloxy)-2-methoxymethoxy-2-methyl-decyl ester

There total 10 articles about 2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-4-allyl-3-hydroxy-5-(4-methoxy-benzyloxy)-2-methoxymethoxy-2-methyl-decyl ester 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: 93.0%

: 3282-30-2
pivaloyl chloride

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

: 327165-28-6
2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-4-allyl-3-hydroxy-5-(4-methoxy-benzyloxy)-2-methoxymethoxy-2-methyl-decyl ester

Guidance literature:: With pyridine; In dichloromethane; at 23 ℃;
DOI:10.1021/ol0069610

Reference yield:

: 123-11-5
4-methoxy-benzaldehyde

: 327165-28-6
2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-4-allyl-3-hydroxy-5-(4-methoxy-benzyloxy)-2-methoxymethoxy-2-methyl-decyl ester

Guidance literature:: Multi-step reaction with 5 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

5.1: 93 percent / pyridine / CH₂Cl₂ / 23 °C

With pyridine; 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

: 327165-28-6
2,2-Dimethyl-propionic acid (2S,3S,4S,5S)-4-allyl-3-hydroxy-5-(4-methoxy-benzyloxy)-2-methoxymethoxy-2-methyl-decyl ester

Guidance literature:: Multi-step reaction with 8 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

8.1: 93 percent / pyridine / CH₂Cl₂ / 23 °C

With pyridine; 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