(4S,6E,8S,10E,12R)-13-((tert-butyldiphenylsilyl)oxy)-8-hydroxy-4,8,12-trimethyltrideca-6,10-dien-1-yl diisopropylcarbamate

Base Information

Chemical Name:(4S,6E,8S,10E,12R)-13-((tert-butyldiphenylsilyl)oxy)-8-hydroxy-4,8,12-trimethyltrideca-6,10-dien-1-yl diisopropylcarbamate
CAS No.:1623736-65-1
Molecular Formula:C₃₉H₆₁NO₄Si
Molecular Weight:636.003
Hs Code.:

Synonyms:(4S,6E,8S,10E,12R)-13-((tert-butyldiphenylsilyl)oxy)-8-hydroxy-4,8,12-trimethyltrideca-6,10-dien-1-yl diisopropylcarbamate

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Chemical Property of (4S,6E,8S,10E,12R)-13-((tert-butyldiphenylsilyl)oxy)-8-hydroxy-4,8,12-trimethyltrideca-6,10-dien-1-yl diisopropylcarbamate

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Technology Process of (4S,6E,8S,10E,12R)-13-((tert-butyldiphenylsilyl)oxy)-8-hydroxy-4,8,12-trimethyltrideca-6,10-dien-1-yl diisopropylcarbamate

There total 13 articles about (4S,6E,8S,10E,12R)-13-((tert-butyldiphenylsilyl)oxy)-8-hydroxy-4,8,12-trimethyltrideca-6,10-dien-1-yl diisopropylcarbamate 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: 96.0%

: (4S,6E,8R,10E,12R)-13-((tert-butyldiphenylsilyl)oxy)-4,8,12-trimethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)trideca-6,10-dien-1-yl diisopropylcarbamate

: 1623736-65-1
(4S,6E,8S,10E,12R)-13-((tert-butyldiphenylsilyl)oxy)-8-hydroxy-4,8,12-trimethyltrideca-6,10-dien-1-yl diisopropylcarbamate

Guidance literature:: With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; water; at 0 ℃; for 0.5h;
DOI:10.1002/anie.201400714

Reference yield:

: 1623736-61-7
(R,E)-tert-butyl((2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pent-3-en-1-yl)oxy)diphenylsilane

: 1623736-65-1
(4S,6E,8S,10E,12R)-13-((tert-butyldiphenylsilyl)oxy)-8-hydroxy-4,8,12-trimethyltrideca-6,10-dien-1-yl diisopropylcarbamate

Guidance literature:: Multi-step reaction with 2 steps

1.1: sec.-butyllithium; N,N,N,N,-tetramethylethylenediamine / hexane; diethyl ether / -78 °C / Inert atmosphere

1.2: 0.53 h / -78 °C / Inert atmosphere

2.1: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C

With N,N,N,N,-tetramethylethylenediamine; dihydrogen peroxide; sec.-butyllithium; sodium hydroxide; In tetrahydrofuran; diethyl ether; hexane; water;
DOI:10.1002/anie.201400714

Reference yield:

: (4S)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-en-3-yl methyl carbonate

: 1623736-65-1
(4S,6E,8S,10E,12R)-13-((tert-butyldiphenylsilyl)oxy)-8-hydroxy-4,8,12-trimethyltrideca-6,10-dien-1-yl diisopropylcarbamate

Guidance literature:: Multi-step reaction with 3 steps

1.1: bis(dibenzylideneacetone)-palladium⁽⁰⁾ / dimethyl sulfoxide / 15 h / Inert atmosphere

2.1: sec.-butyllithium; N,N,N,N,-tetramethylethylenediamine / hexane; diethyl ether / -78 °C / Inert atmosphere

2.2: 0.53 h / -78 °C / Inert atmosphere

3.1: dihydrogen peroxide; sodium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C

With N,N,N,N,-tetramethylethylenediamine; dihydrogen peroxide; sec.-butyllithium; sodium hydroxide; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; hexane; water; dimethyl sulfoxide;
DOI:10.1002/anie.201400714