benzyl ((4R,5R)-5-((R)-1-hydroxy-2-(4-methoxyphenyl)ethyl)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl)carbamate

Base Information

Chemical Name:benzyl ((4R,5R)-5-((R)-1-hydroxy-2-(4-methoxyphenyl)ethyl)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl)carbamate
CAS No.:1292309-31-9
Molecular Formula:C₂₃H₂₉NO₆
Molecular Weight:415.486
Hs Code.:

Synonyms:benzyl ((4R,5R)-5-((R)-1-hydroxy-2-(4-methoxyphenyl)ethyl)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl)carbamate

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Chemical Property of benzyl ((4R,5R)-5-((R)-1-hydroxy-2-(4-methoxyphenyl)ethyl)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl)carbamate

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Technology Process of benzyl ((4R,5R)-5-((R)-1-hydroxy-2-(4-methoxyphenyl)ethyl)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl)carbamate

There total 10 articles about benzyl ((4R,5R)-5-((R)-1-hydroxy-2-(4-methoxyphenyl)ethyl)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl)carbamate 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: 76.0%

: 104-92-7
1-bromo-4-methoxy-benzene

: 1292309-29-5
benzyl ((4R,5S)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolan-4-ylmethyl)carbamate

: 1292309-31-9
benzyl ((4R,5R)-5-((R)-1-hydroxy-2-(4-methoxyphenyl)ethyl)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl)carbamate

Guidance literature:: 1-bromo-4-methoxy-benzene; With iodine; magnesium; In tetrahydrofuran;

benzyl ((4R,5S)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolan-4-ylmethyl)carbamate; With copper(l) cyanide; In tetrahydrofuran; at -78 ℃; for 2h; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; at 0 ℃; stereoselective reaction; Inert atmosphere;
DOI:10.1016/j.tetasy.2011.01.021

Reference yield:

: 1292309-27-3
(R)-2-((4R,5R)-5-((benzyloxycarbonylamino)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl 4-methylbenzenesulfonate

: 1292309-31-9
benzyl ((4R,5R)-5-((R)-1-hydroxy-2-(4-methoxyphenyl)ethyl)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl)carbamate

Guidance literature:: Multi-step reaction with 2 steps

1.1: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere

2.1: iodine; magnesium / tetrahydrofuran

2.2: 2 h / -78 °C / Inert atmosphere

2.3: 0 °C / Inert atmosphere

With iodine; potassium carbonate; magnesium; In tetrahydrofuran; methanol;
DOI:10.1016/j.tetasy.2011.01.021

Reference yield:

: 321549-65-9
(4S,4'R,5R)-5-(azidomethyl)-2,2,2',2'-tetramethyl-4,4'-bis(1,3-dioxolane)

: 1292309-31-9
benzyl ((4R,5R)-5-((R)-1-hydroxy-2-(4-methoxyphenyl)ethyl)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl)carbamate

Guidance literature:: Multi-step reaction with 6 steps

1.1: palladium 10% on activated carbon; hydrogen / methanol / 24 h / 20 °C

2.1: sodium carbonate / dichloromethane / 0 - 20 °C

3.1: water; acetic acid / 20 °C

4.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

5.1: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere

6.1: iodine; magnesium / tetrahydrofuran

6.2: 2 h / -78 °C / Inert atmosphere

6.3: 0 °C / Inert atmosphere

With palladium 10% on activated carbon; water; hydrogen; iodine; di(n-butyl)tin oxide; sodium carbonate; potassium carbonate; magnesium; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/j.tetasy.2011.01.021