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

Base Information

Chemical Name:(2S,3R)-2-(benzyloxy)-5-(tert-butyldimethylsiloxy)-3-[(p-methoxybenzyl)oxy]-2-{[(methoxybenzyl)oxy]methyl}-1-pentanol
CAS No.:228122-05-2
Molecular Formula:C₃₅H₅₀O₇Si
Molecular Weight:610.863
Hs Code.:

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

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Chemical Property of (2S,3R)-2-(benzyloxy)-5-(tert-butyldimethylsiloxy)-3-[(p-methoxybenzyl)oxy]-2-{[(methoxybenzyl)oxy]methyl}-1-pentanol

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Technology Process of (2S,3R)-2-(benzyloxy)-5-(tert-butyldimethylsiloxy)-3-[(p-methoxybenzyl)oxy]-2-{[(methoxybenzyl)oxy]methyl}-1-pentanol

There total 5 articles about (2S,3R)-2-(benzyloxy)-5-(tert-butyldimethylsiloxy)-3-[(p-methoxybenzyl)oxy]-2-{[(methoxybenzyl)oxy]methyl}-1-pentanol 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:

: 228122-17-6
2,2-Dimethyl-propionic acid (2R,3R)-2-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-pentyl ester

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

Guidance literature:: With diisobutylaluminium hydride; at -78 ℃; Yield given;
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

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

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

: 1026599-20-1
(2S,3R)-2-Benzyloxy-3-(4-methoxy-benzyloxy)-2-(4-methoxy-benzyloxymethyl)-pent-4-en-1-ol

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

Guidance literature:: Multi-step reaction with 4 steps

1: 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h

2: 96 percent / 9-BBN; NaOH; H₂O₂ / tetrahydrofuran; H₂O / 15 h

3: imidazole / dimethylformamide / 1 h

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

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