(S)-4-[(2S,4S)-2,4-Bis-(4-methoxy-benzyloxy)-8-phenyl-octyl]-2,2-dimethyl-[1,3]dioxolane

Base Information

Chemical Name:(S)-4-[(2S,4S)-2,4-Bis-(4-methoxy-benzyloxy)-8-phenyl-octyl]-2,2-dimethyl-[1,3]dioxolane
CAS No.:868566-36-3
Molecular Formula:C₃₅H₄₆O₆
Molecular Weight:562.747
Hs Code.:

Synonyms:(S)-4-[(2S,4S)-2,4-Bis-(4-methoxy-benzyloxy)-8-phenyl-octyl]-2,2-dimethyl-[1,3]dioxolane

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Chemical Property of (S)-4-[(2S,4S)-2,4-Bis-(4-methoxy-benzyloxy)-8-phenyl-octyl]-2,2-dimethyl-[1,3]dioxolane

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Technology Process of (S)-4-[(2S,4S)-2,4-Bis-(4-methoxy-benzyloxy)-8-phenyl-octyl]-2,2-dimethyl-[1,3]dioxolane

There total 11 articles about (S)-4-[(2S,4S)-2,4-Bis-(4-methoxy-benzyloxy)-8-phenyl-octyl]-2,2-dimethyl-[1,3]dioxolane 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: 91.0%

: 868566-21-6
(2S,4S)-1-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-8-phenyl-octane-2,4-diol

: 824-94-2
p-methoxybenzyl chloride

: 868566-36-3
(S)-4-[(2S,4S)-2,4-Bis-(4-methoxy-benzyloxy)-8-phenyl-octyl]-2,2-dimethyl-[1,3]dioxolane

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 6h;
DOI:10.1021/jo050972v

Reference yield:

: 868566-22-7
2-O-benzyl-3,5-dideoxy-6,7-O-isopropylidene-D-xyloheptoic-γ-lactone

: 868566-36-3
(S)-4-[(2S,4S)-2,4-Bis-(4-methoxy-benzyloxy)-8-phenyl-octyl]-2,2-dimethyl-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 6 steps

1.1: 97 percent / DIBAL-H / CH₂Cl₂; toluene / 0.5 h / -78 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 20 °C

2.2: 96 percent / tetrahydrofuran; hexane / 12 h / 20 °C

3.1: 69 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 0 °C

4.1: 96 percent / H₂ / Raney nickel / ethanol / 12 h / 1034.3 Torr

5.1: 95 percent / Na / methanol / 2 h / 20 °C

6.1: 91 percent / NaH / dimethylformamide / 6 h / 20 °C

With n-butyllithium; hydrogen; sodium; sodium hydride; diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; nickel; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 2.2: Wittig olefination reaction / 3.1: Mitsunobu reaction;
DOI:10.1021/jo050972v

Reference yield:

: (3R,5S)-3-Benzyloxy-5-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetrahydro-furan-2-ol

: 868566-36-3
(S)-4-[(2S,4S)-2,4-Bis-(4-methoxy-benzyloxy)-8-phenyl-octyl]-2,2-dimethyl-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 20 °C

1.2: 96 percent / tetrahydrofuran; hexane / 12 h / 20 °C

2.1: 69 percent / diethyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 2 h / 0 °C

3.1: 96 percent / H₂ / Raney nickel / ethanol / 12 h / 1034.3 Torr

4.1: 95 percent / Na / methanol / 2 h / 20 °C

5.1: 91 percent / NaH / dimethylformamide / 6 h / 20 °C

With n-butyllithium; hydrogen; sodium; sodium hydride; triphenylphosphine; diethylazodicarboxylate; nickel; In tetrahydrofuran; methanol; ethanol; hexane; N,N-dimethyl-formamide; 1.2: Wittig olefination reaction / 2.1: Mitsunobu reaction;
DOI:10.1021/jo050972v