(2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(2-diazoacetoxy)-6-methylhept-5-en-3-yl benzoate

Base Information

Chemical Name:(2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(2-diazoacetoxy)-6-methylhept-5-en-3-yl benzoate
CAS No.:1265883-16-6
Molecular Formula:C₂₃H₃₄N₂O₅Si
Molecular Weight:446.619
Hs Code.:

Synonyms:(2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(2-diazoacetoxy)-6-methylhept-5-en-3-yl benzoate

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Chemical Property of (2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(2-diazoacetoxy)-6-methylhept-5-en-3-yl benzoate

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Technology Process of (2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(2-diazoacetoxy)-6-methylhept-5-en-3-yl benzoate

There total 4 articles about (2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(2-diazoacetoxy)-6-methylhept-5-en-3-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: 75.0%

: 1265883-27-9
C₂₁H₃₄O₄Si

: 14661-69-9
p-toluenesulfonylhydrazone glyoxylic acid chloride

: 1265883-16-6
(2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(2-diazoacetoxy)-6-methylhept-5-en-3-yl benzoate

Guidance literature:: C₂₁H₃₄O₄Si; p-toluenesulfonylhydrazone glyoxylic acid chloride; With N,N-dimethyl-aniline; In dichloromethane; for 0.25h; Inert atmosphere; Cooling with ice;

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 0.5h; Inert atmosphere;
DOI:10.1021/jo102033h

Reference yield:

: 1265883-18-8
C₁₅H₂₀O₄

: 1265883-16-6
(2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(2-diazoacetoxy)-6-methylhept-5-en-3-yl benzoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: dmap; triethylamine / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; toluene

2.2: -78 °C

3.1: N,N-dimethyl-aniline / dichloromethane / 0.25 h / Inert atmosphere; Cooling with ice

3.2: 0.5 h / 0 - 20 °C / Inert atmosphere

With dmap; N,N-dimethyl-aniline; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo102033h

Reference yield:

: 1265883-20-2
C₂₁H₃₄O₄Si

: 1265883-16-6
(2R,3R)-1-(tert-butyldimethylsilyloxy)-2-(2-diazoacetoxy)-6-methylhept-5-en-3-yl benzoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; toluene

1.2: -78 °C

2.1: N,N-dimethyl-aniline / dichloromethane / 0.25 h / Inert atmosphere; Cooling with ice

2.2: 0.5 h / 0 - 20 °C / Inert atmosphere

With N,N-dimethyl-aniline; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; dimethyl sulfoxide; toluene;
DOI:10.1021/jo102033h