methyl (4S,5R,6R,7R)-5-(benzyloxy)-7-<(tert-butyldimethylsilyl)oxy>-2,4,6-trimethyl-2(E)-nonenate

Base Information

Chemical Name:methyl (4S,5R,6R,7R)-5-(benzyloxy)-7-<(tert-butyldimethylsilyl)oxy>-2,4,6-trimethyl-2(E)-nonenate
CAS No.:131589-25-8
Molecular Formula:C₂₆H₄₄O₄Si
Molecular Weight:448.718
Hs Code.:

Synonyms:methyl (4S,5R,6R,7R)-5-(benzyloxy)-7-<(tert-butyldimethylsilyl)oxy>-2,4,6-trimethyl-2(E)-nonenate

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Chemical Property of methyl (4S,5R,6R,7R)-5-(benzyloxy)-7-<(tert-butyldimethylsilyl)oxy>-2,4,6-trimethyl-2(E)-nonenate

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Technology Process of methyl (4S,5R,6R,7R)-5-(benzyloxy)-7-<(tert-butyldimethylsilyl)oxy>-2,4,6-trimethyl-2(E)-nonenate

There total 9 articles about methyl (4S,5R,6R,7R)-5-(benzyloxy)-7-<(tert-butyldimethylsilyl)oxy>-2,4,6-trimethyl-2(E)-nonenate 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: 95.0%

: 123219-41-0
(2R,3S,4R,5R)-3-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-heptanal

: 2605-68-7
methyl 2-(triphenylphosphoranylidene)propionate

: 131589-25-8
methyl (4S,5R,6R,7R)-5-(benzyloxy)-7-<(tert-butyldimethylsilyl)oxy>-2,4,6-trimethyl-2(E)-nonenate

Guidance literature:: In tetrahydrofuran; at 22 ℃; for 72h;
DOI:10.1021/ja00003a026

Reference yield:

: 100-39-0
benzyl bromide

: 131589-25-8
methyl (4S,5R,6R,7R)-5-(benzyloxy)-7-<(tert-butyldimethylsilyl)oxy>-2,4,6-trimethyl-2(E)-nonenate

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 2.) from -50 deg C to RT, overnight

2: 96 percent / formic acid / diethyl ether / 22 °C

3: oxalyl chloride/DMSO / CH₂Cl₂ / 0.33 h / -78 °C

4: 62 percent / diethyl ether / 2 h / 22 °C

5: 97 percent / imidazole / dimethylformamide / 48 h / 60 °C

6: 1.) ozone, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) from -78 deg C to RT

7: 95 percent / tetrahydrofuran / 72 h / 22 °C

With 1H-imidazole; formic acid; oxalyl dichloride; sodium hydride; ozone; dimethyl sulfoxide; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja00003a026

Reference yield:

: 131589-22-5
(2R,3R,4S)-3-(benzyloxy)-2,4-dimethyl-5-hexanal

: 131589-25-8
methyl (4S,5R,6R,7R)-5-(benzyloxy)-7-<(tert-butyldimethylsilyl)oxy>-2,4,6-trimethyl-2(E)-nonenate

Guidance literature:: Multi-step reaction with 4 steps

1: 62 percent / diethyl ether / 2 h / 22 °C

2: 97 percent / imidazole / dimethylformamide / 48 h / 60 °C

3: 1.) ozone, 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C, 2.) from -78 deg C to RT

4: 95 percent / tetrahydrofuran / 72 h / 22 °C

With 1H-imidazole; ozone; triphenylphosphine; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;
DOI:10.1021/ja00003a026