(2R,4S,7R,8R,9R,11R)-1-azido-9-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-2,4,11-trimethyl-7-(triethylsilyloxy)-14-(trimethylsilyl)tetradec-13-yn-5-one

Base Information

Chemical Name:(2R,4S,7R,8R,9R,11R)-1-azido-9-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-2,4,11-trimethyl-7-(triethylsilyloxy)-14-(trimethylsilyl)tetradec-13-yn-5-one
CAS No.:918310-78-8
Molecular Formula:C₄₀H₇₃N₃O₅Si₃
Molecular Weight:760.293
Hs Code.:

(2R,4S,7R,8R,9R,11R)-1-azido-9-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-2,4,11-trimethyl-7-(triethylsilyloxy)-14-(trimethylsilyl)tetradec-13-yn-5-one

Synonyms:(2R,4S,7R,8R,9R,11R)-1-azido-9-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-2,4,11-trimethyl-7-(triethylsilyloxy)-14-(trimethylsilyl)tetradec-13-yn-5-one

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Chemical Property of (2R,4S,7R,8R,9R,11R)-1-azido-9-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-2,4,11-trimethyl-7-(triethylsilyloxy)-14-(trimethylsilyl)tetradec-13-yn-5-one

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Technology Process of (2R,4S,7R,8R,9R,11R)-1-azido-9-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-2,4,11-trimethyl-7-(triethylsilyloxy)-14-(trimethylsilyl)tetradec-13-yn-5-one

There total 19 articles about (2R,4S,7R,8R,9R,11R)-1-azido-9-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-2,4,11-trimethyl-7-(triethylsilyloxy)-14-(trimethylsilyl)tetradec-13-yn-5-one 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%

: 918310-77-7
(2R,4S,7R,8S,9R,11R)-1-azido-9-(tert-butyldimethylsilyloxy)-7-hydroxy-8-(4-methoxybenzyloxy)-2,4,11-trimethyl-14-(trimethylsilyl)tetradec-13-yn-5-one

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 918310-78-8
(2R,4S,7R,8R,9R,11R)-1-azido-9-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-2,4,11-trimethyl-7-(triethylsilyloxy)-14-(trimethylsilyl)tetradec-13-yn-5-one

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.0833333h;
DOI:10.1021/ja066971h

Reference yield:

: 896730-03-3
(2S,4R)-5-Azido-2,4-dimethyl-pentanal

: 918310-78-8
(2R,4S,7R,8R,9R,11R)-1-azido-9-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-2,4,11-trimethyl-7-(triethylsilyloxy)-14-(trimethylsilyl)tetradec-13-yn-5-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: diethyl ether / 1 h / 0 °C

2.1: 0.41 g / dimethylsulfoxide; N,N-diisopropylethylamine; SO₃*pyridine / CH₂Cl₂ / 1 h

3.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

3.2: tetrahydrofuran / 1 h / -78 °C

4.1: 148 mg / MgBr₂*OEt₂ / CH₂Cl₂ / 12 h / -78 - 20 °C

5.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.08 h / 0 °C

With 2,6-dimethylpyridine; pyridine-SO₃ complex; sodium hexamethyldisilazane; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; magnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; 2.1: Swern oxidation / 4.1: Mukaiyama aldol reaction;
DOI:10.1021/ja066971h

Reference yield:

: 896729-89-8
(3S,5R)-6-azido-3,5-dimethylhexan-2-one

: 918310-78-8
(2R,4S,7R,8R,9R,11R)-1-azido-9-(tert-butyldimethylsilyloxy)-8-(4-methoxybenzyloxy)-2,4,11-trimethyl-7-(triethylsilyloxy)-14-(trimethylsilyl)tetradec-13-yn-5-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

1.2: tetrahydrofuran / 1 h / -78 °C

2.1: 148 mg / MgBr₂*OEt₂ / CH₂Cl₂ / 12 h / -78 - 20 °C

3.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.08 h / 0 °C

With 2,6-dimethylpyridine; sodium hexamethyldisilazane; magnesium bromide; In tetrahydrofuran; dichloromethane; 2.1: Mukaiyama aldol reaction;
DOI:10.1021/ja066971h