tert-butyl ((S)-2-((tert-butyldiphenylsilyl)oxy)-1-((4R,5R)-5-((S)-2-hydroxybutyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)carbamate

Base Information

Chemical Name:tert-butyl ((S)-2-((tert-butyldiphenylsilyl)oxy)-1-((4R,5R)-5-((S)-2-hydroxybutyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)carbamate
CAS No.:1345017-60-8
Molecular Formula:C₃₂H₄₉NO₆Si
Molecular Weight:571.83
Hs Code.:

Synonyms:tert-butyl ((S)-2-((tert-butyldiphenylsilyl)oxy)-1-((4R,5R)-5-((S)-2-hydroxybutyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)carbamate

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Chemical Property of tert-butyl ((S)-2-((tert-butyldiphenylsilyl)oxy)-1-((4R,5R)-5-((S)-2-hydroxybutyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)carbamate

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Technology Process of tert-butyl ((S)-2-((tert-butyldiphenylsilyl)oxy)-1-((4R,5R)-5-((S)-2-hydroxybutyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)carbamate

There total 9 articles about tert-butyl ((S)-2-((tert-butyldiphenylsilyl)oxy)-1-((4R,5R)-5-((S)-2-hydroxybutyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)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: 82.0%

: 1345017-59-5
(S)-1-((4R,5R)-2,2-dimethyl-5-((S)-2,2,10,10-tetramethyl-8-oxo-3,3-diphenyl-4,9-dioxa-7-aza-3-silaundecan-6-yl)-1,3-dioxolan-4-yl)butan-2-yl acetate

: 1345017-60-8
tert-butyl ((S)-2-((tert-butyldiphenylsilyl)oxy)-1-((4R,5R)-5-((S)-2-hydroxybutyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)carbamate

Guidance literature:: With methanol; potassium carbonate; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1016/j.tetlet.2011.08.084

Reference yield:

: 1345017-47-1
(S)-tert-butyl 4-((R)-1-(allyloxy)allyl)-2,2-dimethyloxazolidine-3-carboxylate

: 1345017-60-8
tert-butyl ((S)-2-((tert-butyldiphenylsilyl)oxy)-1-((4R,5R)-5-((S)-2-hydroxybutyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)carbamate

Guidance literature:: Multi-step reaction with 8 steps

1.1: acetic acid / methanol; water / 0 - 20 °C / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 12 h / 0 - 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere

3.2: 0 °C / Inert atmosphere

4.1: sodium tetrahydroborate; cobalt(III) chloride hexahydrate / ethanol / 1 h / 0 - 20 °C / Inert atmosphere

5.1: dmap; triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

6.1: osmium(VIII) oxide; methanesulfonamide; water; sodium hydrogencarbonate; 4-methylmorpholine N-oxide / acetone; toluene / 12 h / 0 - 20 °C / Inert atmosphere

7.1: toluene-4-sulfonic acid / acetone / 3 h / 20 °C / Inert atmosphere

8.1: methanol; potassium carbonate / 2 h / 20 °C / Inert atmosphere

With 1H-imidazole; methanol; dmap; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; methanesulfonamide; cobalt(III) chloride hexahydrate; water; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; acetone; toluene; 3.1: Wittig rearrangement;
DOI:10.1016/j.tetlet.2011.08.084

Reference yield:

: 1345017-49-3
tert-butyl (2S,3R)-3-(allyloxy)-1-(tert-butyldiphenylsilyloxy)pent-4-en-2-ylcarbamate

: 1345017-60-8
tert-butyl ((S)-2-((tert-butyldiphenylsilyl)oxy)-1-((4R,5R)-5-((S)-2-hydroxybutyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl)carbamate

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - 0 °C / Inert atmosphere

1.2: 0 °C / Inert atmosphere

2.1: sodium tetrahydroborate; cobalt(III) chloride hexahydrate / ethanol / 1 h / 0 - 20 °C / Inert atmosphere

3.1: dmap; triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

4.1: osmium(VIII) oxide; methanesulfonamide; water; sodium hydrogencarbonate; 4-methylmorpholine N-oxide / acetone; toluene / 12 h / 0 - 20 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / acetone / 3 h / 20 °C / Inert atmosphere

6.1: methanol; potassium carbonate / 2 h / 20 °C / Inert atmosphere

With methanol; dmap; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; methanesulfonamide; cobalt(III) chloride hexahydrate; water; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetone; toluene; 1.1: Wittig rearrangement;
DOI:10.1016/j.tetlet.2011.08.084