(S,Z)-allyl 1-((5-hydroxy-1-tritylthiopent-2-en-2-yl)(methyl)amino)-1-oxopropan-2-ylcarbamate

Base Information

Chemical Name:(S,Z)-allyl 1-((5-hydroxy-1-tritylthiopent-2-en-2-yl)(methyl)amino)-1-oxopropan-2-ylcarbamate
CAS No.:1314777-79-1
Molecular Formula:C₃₂H₃₆N₂O₄S
Molecular Weight:544.715
Hs Code.:

Synonyms:(S,Z)-allyl 1-((5-hydroxy-1-tritylthiopent-2-en-2-yl)(methyl)amino)-1-oxopropan-2-ylcarbamate

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Chemical Property of (S,Z)-allyl 1-((5-hydroxy-1-tritylthiopent-2-en-2-yl)(methyl)amino)-1-oxopropan-2-ylcarbamate

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Technology Process of (S,Z)-allyl 1-((5-hydroxy-1-tritylthiopent-2-en-2-yl)(methyl)amino)-1-oxopropan-2-ylcarbamate

There total 5 articles about (S,Z)-allyl 1-((5-hydroxy-1-tritylthiopent-2-en-2-yl)(methyl)amino)-1-oxopropan-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: 94.0%

: 1314778-28-3
(S,Z)-allyl 1-((5-(tert-butyldimethylsilyloxy)-1-tritylthiopent-2-en-2-yl)(methyl)amino)-1-oxopropan-2-ylcarbamate

: 1314777-79-1
(S,Z)-allyl 1-((5-hydroxy-1-tritylthiopent-2-en-2-yl)(methyl)amino)-1-oxopropan-2-ylcarbamate

Guidance literature:: (S,Z)-allyl 1-((5-(tert-butyldimethylsilyloxy)-1-tritylthiopent-2-en-2-yl)(methyl)amino)-1-oxopropan-2-ylcarbamate; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 1h;

With ammonium chloride; In tetrahydrofuran; water;
DOI:10.1021/ja204088a

Reference yield:

: 1314777-76-8
(Z)-5-(tert-butyldimethylsilyloxy)-2-iodopent-2-en-1-ol

: 1314777-79-1
(S,Z)-allyl 1-((5-hydroxy-1-tritylthiopent-2-en-2-yl)(methyl)amino)-1-oxopropan-2-ylcarbamate

Guidance literature:: Multi-step reaction with 4 steps

1: copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 50 - 60 °C / Inert atmosphere; Sonication

2: diisopropyl azodicarboxylate; triphenylphosphine / dichloromethane / 20 °C / Inert atmosphere; Reflux

3: potassium carbonate / N,N-dimethyl-formamide / 48 h / 20 °C

4: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C

With copper(l) iodide; diisopropyl azodicarboxylate; tetrabutyl ammonium fluoride; potassium carbonate; caesium carbonate; triphenylphosphine; N,N`-dimethylethylenediamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; 2: Mitsunobu reaction;
DOI:10.1021/ja204088a

Reference yield:

: 90134-46-6
5-[(tert-butyldimethylsilyl)oxy]pent-2-yn-1-ol

: 1314777-79-1
(S,Z)-allyl 1-((5-hydroxy-1-tritylthiopent-2-en-2-yl)(methyl)amino)-1-oxopropan-2-ylcarbamate

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-butyllithium / tetrahydrofuran; cyclohexane / 0.17 h / -23 °C / Inert atmosphere

1.2: 60 h / 35 °C / Inert atmosphere

1.3: 0.33 h / -78 °C / Inert atmosphere

2.1: copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 50 - 60 °C / Inert atmosphere; Sonication

3.1: diisopropyl azodicarboxylate; triphenylphosphine / dichloromethane / 20 °C / Inert atmosphere; Reflux

4.1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 20 °C

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C

With copper(l) iodide; n-butyllithium; diisopropyl azodicarboxylate; tetrabutyl ammonium fluoride; potassium carbonate; caesium carbonate; triphenylphosphine; N,N`-dimethylethylenediamine; In tetrahydrofuran; 1,4-dioxane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; 3.1: Mitsunobu reaction;
DOI:10.1021/ja204088a