(4S,5R)-4-[(4-methoxybenzyloxy)methyl]-2,2-dimethyl-5-(oct-2-ynyl)-1,3-dioxolane

Base Information

Chemical Name:(4S,5R)-4-[(4-methoxybenzyloxy)methyl]-2,2-dimethyl-5-(oct-2-ynyl)-1,3-dioxolane
CAS No.:1277164-63-2
Molecular Formula:C₂₂H₃₂O₄
Molecular Weight:360.494
Hs Code.:

Synonyms:(4S,5R)-4-[(4-methoxybenzyloxy)methyl]-2,2-dimethyl-5-(oct-2-ynyl)-1,3-dioxolane

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Chemical Property of (4S,5R)-4-[(4-methoxybenzyloxy)methyl]-2,2-dimethyl-5-(oct-2-ynyl)-1,3-dioxolane

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Technology Process of (4S,5R)-4-[(4-methoxybenzyloxy)methyl]-2,2-dimethyl-5-(oct-2-ynyl)-1,3-dioxolane

There total 6 articles about (4S,5R)-4-[(4-methoxybenzyloxy)methyl]-2,2-dimethyl-5-(oct-2-ynyl)-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: 89.0%

: 1277164-60-9
(2S,3R)-1-(4-methoxybenzyloxy)undec-5-yne-2,3-diol

: 77-76-9
2,2-dimethoxy-propane

: 1277164-63-2
(4S,5R)-4-[(4-methoxybenzyloxy)methyl]-2,2-dimethyl-5-(oct-2-ynyl)-1,3-dioxolane

Guidance literature:: With (R)-10-camphorsulfonic acid; In dichloromethane; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1002/ejoc.201001378

Reference yield:

: 1277164-62-1
(Z)-1-methoxy-4-[(undec-2-en-5-ynyloxy)methyl]benzene

: 1277164-63-2
(4S,5R)-4-[(4-methoxybenzyloxy)methyl]-2,2-dimethyl-5-(oct-2-ynyl)-1,3-dioxolane

Guidance literature:: Multi-step reaction with 2 steps

1.1: AD-mix α / water; tert-butyl alcohol / 1 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: (R)-10-camphorsulfonic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

With AD-mix α; (R)-10-camphorsulfonic acid; In dichloromethane; water; tert-butyl alcohol; 1.1: Sharpless dihydroxylation / 1.2: Sharpless dihydroxylation;
DOI:10.1002/ejoc.201001378

Reference yield:

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 1277164-63-2
(4S,5R)-4-[(4-methoxybenzyloxy)methyl]-2,2-dimethyl-5-(oct-2-ynyl)-1,3-dioxolane

Guidance literature:: Multi-step reaction with 5 steps

1.1: (R)-10-camphorsulfonic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: carbon tetrabromide; triphenylphosphine / dichloromethane / 0 - 20 °C / Inert atmosphere

3.1: copper(l) iodide; potassium carbonate; sodium iodide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

4.1: AD-mix α / water; tert-butyl alcohol / 1 h / 0 °C / Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere

5.1: (R)-10-camphorsulfonic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

With copper(l) iodide; carbon tetrabromide; AD-mix α; (R)-10-camphorsulfonic acid; potassium carbonate; triphenylphosphine; sodium iodide; In dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 2.1: Appel reaction / 4.1: Sharpless dihydroxylation / 4.2: Sharpless dihydroxylation;
DOI:10.1002/ejoc.201001378