benzyl (2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-1-hydroxy-5-(4-methoxybenzyloxy)-4-methylpentan-2-ylcarbamate

Base Information

Chemical Name:benzyl (2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-1-hydroxy-5-(4-methoxybenzyloxy)-4-methylpentan-2-ylcarbamate
CAS No.:1427215-68-6
Molecular Formula:C₂₈H₄₃NO₆Si
Molecular Weight:517.738
Hs Code.:

Synonyms:benzyl (2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-1-hydroxy-5-(4-methoxybenzyloxy)-4-methylpentan-2-ylcarbamate

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Chemical Property of benzyl (2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-1-hydroxy-5-(4-methoxybenzyloxy)-4-methylpentan-2-ylcarbamate

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Technology Process of benzyl (2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-1-hydroxy-5-(4-methoxybenzyloxy)-4-methylpentan-2-ylcarbamate

There total 8 articles about benzyl (2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-1-hydroxy-5-(4-methoxybenzyloxy)-4-methylpentan-2-ylcarbamate 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: 80.0%

: 1427215-67-5
benzyl (5R,6R)-5-((R)-1-(4-methoxybenzyloxy)propan-2-yl)-2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecan-6-ylcarbamate

: 1427215-68-6
benzyl (2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-1-hydroxy-5-(4-methoxybenzyloxy)-4-methylpentan-2-ylcarbamate

Guidance literature:: With toluene-4-sulfonic acid; In methanol; at 0 ℃; for 2h;
DOI:10.1016/j.tetlet.2013.02.032

Reference yield:

: 212051-35-9
(R)-methyl 3-((4-methoxybenzyl)oxy)-2-methylpropanoate

: 1427215-68-6
benzyl (2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-1-hydroxy-5-(4-methoxybenzyloxy)-4-methylpentan-2-ylcarbamate

Guidance literature:: Multi-step reaction with 8 steps

1.1: diisobutylaluminium hydride / toluene; hexane; methanol / 2 h / 20 °C

1.2: 2 h / -78 °C

2.1: diisobutylaluminium hydride / toluene; dichloromethane / 1 h / -78 °C

3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2.5 h / -10 - 0 °C

4.1: sodium azide; Trimethylboroxine / N,N-dimethyl-formamide / 18 h / 60 °C

4.2: 0.33 h / 20 °C

5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / -78 °C / Inert atmosphere

6.1: triphenylphosphine / tetrahydrofuran; water / 6.5 h / 45 °C

7.1: triethylamine / tetrahydrofuran / 2 h / 0 - 20 °C

8.1: toluene-4-sulfonic acid / methanol / 2 h / 0 °C

With sodium azide; Trimethylboroxine; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.2: |Horner-Wadsworth-Emmons Olefination / 6.1: |Staudinger Azide Reduction / 7.1: |Staudinger Azide Reduction;
DOI:10.1016/j.tetlet.2013.02.032

Reference yield:

: 1427215-75-5
C₂₆H₅₁NO₄Si₂

: 1427215-68-6
benzyl (2R,3R,4R)-3-(tert-butyldimethylsilyloxy)-1-hydroxy-5-(4-methoxybenzyloxy)-4-methylpentan-2-ylcarbamate

Guidance literature:: Multi-step reaction with 2 steps

1: triethylamine / tetrahydrofuran / 2 h / 0 - 20 °C

2: toluene-4-sulfonic acid / methanol / 2 h / 0 °C

With toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; 1: |Staudinger Azide Reduction;
DOI:10.1016/j.tetlet.2013.02.032