1-{5-[1-benzyloxycarbonylamino-2-(tert-butyldiphenylsilyloxy)ethyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethyl methanesulfonate

Base Information

Chemical Name:1-{5-[1-benzyloxycarbonylamino-2-(tert-butyldiphenylsilyloxy)ethyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethyl methanesulfonate
CAS No.:1360594-50-8
Molecular Formula:C₃₄H₄₅NO₈SSi
Molecular Weight:655.885
Hs Code.:

Synonyms:1-{5-[1-benzyloxycarbonylamino-2-(tert-butyldiphenylsilyloxy)ethyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethyl methanesulfonate

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Chemical Property of 1-{5-[1-benzyloxycarbonylamino-2-(tert-butyldiphenylsilyloxy)ethyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethyl methanesulfonate

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Technology Process of 1-{5-[1-benzyloxycarbonylamino-2-(tert-butyldiphenylsilyloxy)ethyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethyl methanesulfonate

There total 9 articles about 1-{5-[1-benzyloxycarbonylamino-2-(tert-butyldiphenylsilyloxy)ethyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethyl methanesulfonate 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: 86.0%

: 1360594-49-5
benzyl {2-(tert-butyldiphenylsilyloxy)-1-[5-(1-hydroxyethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]ethyl}carbamate

: 124-63-0
methanesulfonyl chloride

: 1360594-50-8
1-{5-[1-benzyloxycarbonylamino-2-(tert-butyldiphenylsilyloxy)ethyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethyl methanesulfonate

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 20 ℃; for 1h; Inert atmosphere;
DOI:10.1002/ejoc.201100968

Reference yield:

: 1138325-27-5
(R)-2-(benzyloxy)-1-((4S,5S)-5-((R)-2-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl methanesulfonate

: 1360594-50-8
1-{5-[1-benzyloxycarbonylamino-2-(tert-butyldiphenylsilyloxy)ethyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethyl methanesulfonate

Guidance literature:: Multi-step reaction with 7 steps

1: palladium 10% on activated carbon; hydrogen / ethanol / 72 h / 3102.97 Torr

2: potassium carbonate / methanol / 20 °C / Inert atmosphere

3: pyridine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

4: sodium azide / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

5: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 760.05 Torr

6: sodium hydrogencarbonate / dichloromethane / 6 h / 20 °C / Inert atmosphere

7: triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

With pyridine; sodium azide; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; potassium carbonate; triethylamine; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201100968

Reference yield:

: 1138325-28-6
(R)-1-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)-2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl methanesulfonate

: 1360594-50-8
1-{5-[1-benzyloxycarbonylamino-2-(tert-butyldiphenylsilyloxy)ethyl]-2,2-dimethyl-1,3-dioxolan-4-yl}ethyl methanesulfonate

Guidance literature:: Multi-step reaction with 6 steps

1: potassium carbonate / methanol / 20 °C / Inert atmosphere

2: pyridine / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

3: sodium azide / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

4: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 760.05 Torr

5: sodium hydrogencarbonate / dichloromethane / 6 h / 20 °C / Inert atmosphere

6: triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

With pyridine; sodium azide; palladium 10% on activated carbon; hydrogen; sodium hydrogencarbonate; potassium carbonate; triethylamine; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.201100968