(2S,3R)-2-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-pentanal

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Chemical Name:(2S,3R)-2-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-pentanal
CAS No.:228122-18-7
Molecular Formula:C₃₅H₄₈O₇Si
Molecular Weight:608.847
Hs Code.:

Synonyms:(2S,3R)-2-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-pentanal

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Chemical Property of (2S,3R)-2-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-pentanal

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Technology Process of (2S,3R)-2-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-pentanal

There total 6 articles about (2S,3R)-2-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-pentanal 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%

: 228122-05-2
(2S,3R)-2-(benzyloxy)-5-(tert-butyldimethylsiloxy)-3-[(p-methoxybenzyl)oxy]-2-{[(methoxybenzyl)oxy]methyl}-1-pentanol

: 228122-18-7
(2S,3R)-2-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-pentanal

Guidance literature:: Swern oxidation;
DOI:10.1016/S0040-4039(99)00546-8

Reference yield:

: 217819-76-6
(2S,3R)-2-(benzyloxy)-3-<(p-methoxybenzyl)oxy>-2-<<(p-methoxybenzyl)oxy>methyl>-4-pentenal

: 228122-18-7
(2S,3R)-2-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-pentanal

Guidance literature:: Multi-step reaction with 6 steps

1: LiAlH₄ / diethyl ether / 0.5 h

2: 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h

3: 96 percent / 9-BBN; NaOH; H₂O₂ / tetrahydrofuran; H₂O / 15 h

4: imidazole / dimethylformamide / 1 h

5: DIBAH-L / CH₂Cl₂; hexane / 1 h / -78 °C

6: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

With 1H-imidazole; dmap; sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; dihydrogen peroxide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; 1: Reduction / 2: Acylation / 3: hydroboration / 4: Etherification / 5: Reduction / 6: Oxidation;
DOI:10.1002/1099-0690(200006)2000:12<2187::AID-EJOC2187<3.0.CO;2-2

Reference yield:

: 228122-04-1
(2S,3R)-2-(benzyloxy)-5-hydroxy-3-[(p-methoxybenzyl)oxy]-2-{[(p-methoxybenzyl)oxy]methyl}-4-pentyl pivalate

: 228122-18-7
(2S,3R)-2-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-pentanal

Guidance literature:: Multi-step reaction with 3 steps

1: imidazole / dimethylformamide / 1 h

2: DIBAH-L / CH₂Cl₂; hexane / 1 h / -78 °C

3: 96 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

With 1H-imidazole; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In hexane; dichloromethane; N,N-dimethyl-formamide; 1: Etherification / 2: Reduction / 3: Oxidation;
DOI:10.1002/1099-0690(200006)2000:12<2187::AID-EJOC2187<3.0.CO;2-2