(2S,8R,11S,Z)-7-(benzyldimethylsilyl)-8-((tert-butyldimethylsilyl)oxy)-11-hydroxy-14-methoxy-14-oxotetradec-6-en-12-yn-2-yl benzoate

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Chemical Name:(2S,8R,11S,Z)-7-(benzyldimethylsilyl)-8-((tert-butyldimethylsilyl)oxy)-11-hydroxy-14-methoxy-14-oxotetradec-6-en-12-yn-2-yl benzoate
CAS No.:1361250-52-3
Molecular Formula:C₃₇H₅₄O₆Si₂
Molecular Weight:651.003
Hs Code.:

Synonyms:(2S,8R,11S,Z)-7-(benzyldimethylsilyl)-8-((tert-butyldimethylsilyl)oxy)-11-hydroxy-14-methoxy-14-oxotetradec-6-en-12-yn-2-yl benzoate

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Chemical Property of (2S,8R,11S,Z)-7-(benzyldimethylsilyl)-8-((tert-butyldimethylsilyl)oxy)-11-hydroxy-14-methoxy-14-oxotetradec-6-en-12-yn-2-yl benzoate

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Technology Process of (2S,8R,11S,Z)-7-(benzyldimethylsilyl)-8-((tert-butyldimethylsilyl)oxy)-11-hydroxy-14-methoxy-14-oxotetradec-6-en-12-yn-2-yl benzoate

There total 10 articles about (2S,8R,11S,Z)-7-(benzyldimethylsilyl)-8-((tert-butyldimethylsilyl)oxy)-11-hydroxy-14-methoxy-14-oxotetradec-6-en-12-yn-2-yl benzoate 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: 71.0%

: 1361250-51-2
(2S,8R,Z)-7-(benzyldimethylsilyl)-8-((tert-butyldimethylsilyl)oxy)-11-oxoundec-6-en-2-yl benzoate

: 922-67-8
propynoic acid methyl ester

: 1361250-52-3
(2S,8R,11S,Z)-7-(benzyldimethylsilyl)-8-((tert-butyldimethylsilyl)oxy)-11-hydroxy-14-methoxy-14-oxotetradec-6-en-12-yn-2-yl benzoate

: (2S,8R,11R,Z)-7-(benzyldimethylsilyl)-8-((tert-butyldimethylsilyl)oxy)-11-hydroxy-14-methoxy-14-oxotetradec-6-en-12-yn-2-yl benzoate

Guidance literature:: propynoic acid methyl ester; With (R,R)-(-)-2,6-bis[2-(hydroxyldiphenylmethyl)-1-pyrrolidinyl-methyl]-4-methylphenole; dimethyl zinc(II); In toluene; at 0 - 20 ℃; for 1h; Inert atmosphere;

(2S,8R,Z)-7-(benzyldimethylsilyl)-8-((tert-butyldimethylsilyl)oxy)-11-oxoundec-6-en-2-yl benzoate; In toluene; at 0 - 4 ℃; for 48h; diastereoselective reaction; Inert atmosphere;
DOI:10.1002/chem.201202085

Reference yield:

: 1361250-47-6
(S)-hept-6-yn-2-yl benzoate

: 1361250-52-3
(2S,8R,11S,Z)-7-(benzyldimethylsilyl)-8-((tert-butyldimethylsilyl)oxy)-11-hydroxy-14-methoxy-14-oxotetradec-6-en-12-yn-2-yl benzoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: dimethyl zinc(II); Triphenylphosphine oxide; ((2S,2'S)-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(pyrrolidine-1,2-diyl))bis(diphenylmethanol) / toluene / 0 - 20 °C / Inert atmosphere

1.2: 48 h / 0 - 4 °C / Inert atmosphere

2.1: tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate / 1,2-dichloro-ethane / 0 - 20 °C / Inert atmosphere

3.1: Wilkinson's catalyst; hydrogen / tetrahydrofuran; tert-butyl alcohol / 10 h / 20 °C / Inert atmosphere

4.1: 1H-imidazole / N,N-dimethyl-formamide / 9 h / 20 °C / Inert atmosphere

5.1: pyridinium p-toluenesulfonate / water; acetone / 4 h / 60 °C / Inert atmosphere

6.1: dimethyl zinc(II); ((2S,2'S)-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(pyrrolidine-1,2-diyl))bis(diphenylmethanol) / toluene / 0 - 20 °C / Inert atmosphere

6.2: 48 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; Wilkinson's catalyst; tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate; hydrogen; dimethyl zinc(II); pyridinium p-toluenesulfonate; Triphenylphosphine oxide; ((2S,2'S)-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(pyrrolidine-1,2-diyl))bis(diphenylmethanol); In tetrahydrofuran; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
DOI:10.1021/ol300200m

Reference yield:

: 1361250-58-9
(2S,8R,E)-8-hydroxy-11,11-dimethoxyundec-9-en-6-yn-2-yl benzoate

: 1361250-52-3
(2S,8R,11S,Z)-7-(benzyldimethylsilyl)-8-((tert-butyldimethylsilyl)oxy)-11-hydroxy-14-methoxy-14-oxotetradec-6-en-12-yn-2-yl benzoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate / 1,2-dichloro-ethane / 0 - 20 °C / Inert atmosphere

2.1: Wilkinson's catalyst; hydrogen / tetrahydrofuran; tert-butyl alcohol / 10 h / 20 °C / Inert atmosphere

3.1: 1H-imidazole / N,N-dimethyl-formamide / 9 h / 20 °C / Inert atmosphere

4.1: pyridinium p-toluenesulfonate / water; acetone / 4 h / 60 °C / Inert atmosphere

5.1: dimethyl zinc(II); ((2S,2'S)-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(pyrrolidine-1,2-diyl))bis(diphenylmethanol) / toluene / 0 - 20 °C / Inert atmosphere

5.2: 48 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; Wilkinson's catalyst; tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate; hydrogen; dimethyl zinc(II); pyridinium p-toluenesulfonate; ((2S,2'S)-((2-hydroxy-5-methyl-1,3-phenylene)bis(methylene))bis(pyrrolidine-1,2-diyl))bis(diphenylmethanol); In tetrahydrofuran; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;
DOI:10.1021/ol300200m