(2R,3S,4R,6E)-3-[(4-methoxyphenyl)methoxy]-4-methyl-8-pivaloyloxy-6-octene-1,2-diol

Base Information

Chemical Name:(2R,3S,4R,6E)-3-[(4-methoxyphenyl)methoxy]-4-methyl-8-pivaloyloxy-6-octene-1,2-diol
CAS No.:377751-00-3
Molecular Formula:C₂₂H₃₄O₆
Molecular Weight:394.508
Hs Code.:

Synonyms:(2R,3S,4R,6E)-3-[(4-methoxyphenyl)methoxy]-4-methyl-8-pivaloyloxy-6-octene-1,2-diol

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Chemical Property of (2R,3S,4R,6E)-3-[(4-methoxyphenyl)methoxy]-4-methyl-8-pivaloyloxy-6-octene-1,2-diol

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Technology Process of (2R,3S,4R,6E)-3-[(4-methoxyphenyl)methoxy]-4-methyl-8-pivaloyloxy-6-octene-1,2-diol

There total 9 articles about (2R,3S,4R,6E)-3-[(4-methoxyphenyl)methoxy]-4-methyl-8-pivaloyloxy-6-octene-1,2-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: 95.0%

: 377750-99-7
(2E,5R,6S,7R)-7,8-(isopropylidene)dioxy-6-[(4-methoxyphenyl)methoxy]-5-methyl-1-pivaloyloxy-2-octene

: 377751-00-3
(2R,3S,4R,6E)-3-[(4-methoxyphenyl)methoxy]-4-methyl-8-pivaloyloxy-6-octene-1,2-diol

Guidance literature:: With acetic acid; In tetrahydrofuran; at 40 ℃; for 18h;
DOI:10.1021/ol016449u

Reference yield:

: 88406-01-3
2,3-O-isopropylidene-1-C-<(1R)-1-methylprop-2-enyl>-D-erythro-glycerol

: 377751-00-3
(2R,3S,4R,6E)-3-[(4-methoxyphenyl)methoxy]-4-methyl-8-pivaloyloxy-6-octene-1,2-diol

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

1.2: 93 percent / dimethylformamide / 2 h / 0 °C

2.1: BH₃*SMe₂ / tetrahydrofuran / 2 h

2.2: 77 percent / aq. H₂O₂; NaOH / tetrahydrofuran; ethanol / 3.5 h

3.1: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / 0.5 h / 20 °C

4.1: 616 mg / benzene / 14 h / 20 °C

5.1: 97 percent / DIBALH / CH₂Cl₂; toluene / 1 h / -78 °C

6.1: 97 percent / Et₃N / pyridine / 2 h / 0 °C

7.1: 95 percent / aq. AcOH / tetrahydrofuran / 18 h / 40 °C

With oxalyl dichloride; dimethylsulfide borane complex; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 3.1: Swern oxidation / 4.1: Wittig reaction;
DOI:10.1021/ol016449u

Reference yield:

: 3282-30-2
pivaloyl chloride

: 377751-00-3
(2R,3S,4R,6E)-3-[(4-methoxyphenyl)methoxy]-4-methyl-8-pivaloyloxy-6-octene-1,2-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 97 percent / Et₃N / pyridine / 2 h / 0 °C

2: 95 percent / aq. AcOH / tetrahydrofuran / 18 h / 40 °C

With acetic acid; triethylamine; In tetrahydrofuran; pyridine;
DOI:10.1021/ol016449u