(3R,4S,5R)-5,6-(isopropylidene)dioxy-4-[(4-methoxyphenyl)methoxy]-3-methyl-1-hexene

Base Information

Chemical Name:(3R,4S,5R)-5,6-(isopropylidene)dioxy-4-[(4-methoxyphenyl)methoxy]-3-methyl-1-hexene
CAS No.:377750-95-3
Molecular Formula:C₁₈H₂₆O₄
Molecular Weight:306.402
Hs Code.:

Synonyms:(3R,4S,5R)-5,6-(isopropylidene)dioxy-4-[(4-methoxyphenyl)methoxy]-3-methyl-1-hexene

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Chemical Property of (3R,4S,5R)-5,6-(isopropylidene)dioxy-4-[(4-methoxyphenyl)methoxy]-3-methyl-1-hexene

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Technology Process of (3R,4S,5R)-5,6-(isopropylidene)dioxy-4-[(4-methoxyphenyl)methoxy]-3-methyl-1-hexene

There total 1 articles about (3R,4S,5R)-5,6-(isopropylidene)dioxy-4-[(4-methoxyphenyl)methoxy]-3-methyl-1-hexene 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%

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

: 824-94-2
p-methoxybenzyl chloride

: 377750-95-3
(3R,4S,5R)-5,6-(isopropylidene)dioxy-4-[(4-methoxyphenyl)methoxy]-3-methyl-1-hexene

Guidance literature:: 2,3-O-isopropylidene-1-C-<(1R)-1-methylprop-2-enyl>-D-erythro-glycerol; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;

p-methoxybenzyl chloride; In N,N-dimethyl-formamide; at 0 ℃; for 2h; Further stages.;
DOI:10.1021/ol016449u

Reference yield: 77.0%

: 377750-95-3
(3R,4S,5R)-5,6-(isopropylidene)dioxy-4-[(4-methoxyphenyl)methoxy]-3-methyl-1-hexene

: (3R,4S)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-(4-methoxy-benzyloxy)-3-methyl-butan-2-ol

: 377750-96-4
(3R,4S,5R)-5,6-(isopropylidene)dioxy-4-[(4-methoxyphenyl)methoxy]-3-methyl-1-hexanol

Guidance literature:: (3R,4S,5R)-5,6-(isopropylidene)dioxy-4-[(4-methoxyphenyl)methoxy]-3-methyl-1-hexene; With dimethylsulfide borane complex; In tetrahydrofuran; for 2h;

With sodium hydroxide; dihydrogen peroxide; In tetrahydrofuran; ethanol; for 3.5h; Further stages.;
DOI:10.1021/ol016449u

Reference yield:

: 377750-95-3
(3R,4S,5R)-5,6-(isopropylidene)dioxy-4-[(4-methoxyphenyl)methoxy]-3-methyl-1-hexene

: 377751-14-9
(2E,5R,6S,7Z,9E)-6-[(4-methoxyphenyl)methoxy]-5-methyl-12-(triphenylmethoxy)-2,7,9-dodecatrien-1-ol

Guidance literature:: Multi-step reaction with 14 steps

1.1: BH₃*SMe₂ / tetrahydrofuran / 2 h

1.2: 77 percent / aq. H₂O₂; NaOH / tetrahydrofuran; ethanol / 3.5 h

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

3.1: 616 mg / benzene / 14 h / 20 °C

4.1: 97 percent / DIBALH / CH₂Cl₂; toluene / 1 h / -78 °C

5.1: 97 percent / Et₃N / pyridine / 2 h / 0 °C

6.1: 95 percent / aq. AcOH / tetrahydrofuran / 18 h / 40 °C

7.1: NaIO₄ / methanol; H₂O / 0.5 h / 0 °C

8.1: 302 mg / Ph₃P / CH₂Cl₂ / 1 h / -78 °C

9.1: 97 percent / DIBALH / CH₂Cl₂; toluene / 0.5 h / -78 °C

10.1: 97 percent / imidazole / dimethylformamide / 1.5 h

11.1: 80 percent / BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

12.1: 91 percent / Pd(PPh₃)4; CuI; Et₃N / 2.5 h / 20 °C

13.1: 66 percent / H₂; 1-hexene; quinoline / Lindlar catalyst / 2 h / 20 °C

14.1: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h / 0 °C

With 1H-imidazole; quinoline; sodium periodate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; 1-hexene; oxalyl dichloride; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene; 2.1: Swern oxidation / 3.1: Wittig reaction / 8.1: Corey-Fuchs homologation / 12.1: Sonogashira coupling;
DOI:10.1021/ol016449u