(4S,5R)-4-{[(4-methoxybenzyl)oxy]methyl}-2,2-dimethyl-5-(prop-1-yn-1-yl)-1,3-dioxolane

Base Information

Chemical Name:(4S,5R)-4-{[(4-methoxybenzyl)oxy]methyl}-2,2-dimethyl-5-(prop-1-yn-1-yl)-1,3-dioxolane
CAS No.:1610971-47-5
Molecular Formula:C₁₇H₂₂O₄
Molecular Weight:290.359
Hs Code.:

Synonyms:(4S,5R)-4-{[(4-methoxybenzyl)oxy]methyl}-2,2-dimethyl-5-(prop-1-yn-1-yl)-1,3-dioxolane

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Chemical Property of (4S,5R)-4-{[(4-methoxybenzyl)oxy]methyl}-2,2-dimethyl-5-(prop-1-yn-1-yl)-1,3-dioxolane

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Technology Process of (4S,5R)-4-{[(4-methoxybenzyl)oxy]methyl}-2,2-dimethyl-5-(prop-1-yn-1-yl)-1,3-dioxolane

There total 6 articles about (4S,5R)-4-{[(4-methoxybenzyl)oxy]methyl}-2,2-dimethyl-5-(prop-1-yn-1-yl)-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: 99.0%

: 1610971-46-4
C₁₆H₂₀O₄

: 74-88-4
methyl iodide

: 1610971-47-5
(4S,5R)-4-{[(4-methoxybenzyl)oxy]methyl}-2,2-dimethyl-5-(prop-1-yn-1-yl)-1,3-dioxolane

Guidance literature:: C₁₆H₂₀O₄; With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; hexane; at -78 - 20 ℃; Inert atmosphere;
DOI:10.1002/ejoc.201301487 DOI:10.1002/ejoc.201301487

Reference yield:

: 213767-09-0
2,3-O-isopropylidene-L-erythrofuranose

: 1610971-47-5
(4S,5R)-4-{[(4-methoxybenzyl)oxy]methyl}-2,2-dimethyl-5-(prop-1-yn-1-yl)-1,3-dioxolane

Guidance literature:: Multi-step reaction with 3 steps

1.1: diazomethyl-trimethyl-silane; lithium diisopropyl amide / tetrahydrofuran / -78 - 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

2.2: 3 h / 0 - 20 °C / Inert atmosphere

3.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; sodium hydride; lithium diisopropyl amide; diazomethyl-trimethyl-silane; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; 1.1: |Colvin Alkyne Synthesis;
DOI:10.1002/ejoc.201301487

Reference yield:

: 127305-55-9
[(4S,5R)-5-ethynyl-2,2-dimethyl-1,3-dioxolan-4-yl]methanol

: 1610971-47-5
(4S,5R)-4-{[(4-methoxybenzyl)oxy]methyl}-2,2-dimethyl-5-(prop-1-yn-1-yl)-1,3-dioxolane

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

1.2: 3 h / 0 - 20 °C / Inert atmosphere

2.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; sodium hydride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201301487 DOI:10.1002/ejoc.201301487