(R)-4-(benzyloxy)-1-((2R,5S)-5-((S)-hydroxy((2R,4S,5R)-5-(hydroxymethyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)butan-1-ol

Base Information

• Chemical Name: (R)-4-(benzyloxy)-1-((2R,5S)-5-((S)-hydroxy((2R,4S,5R)-5-(hydroxymethyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)butan-1-ol
• CAS No.: 1448328-56-0
• Molecular Formula: C₃₀H₄₂O₈
• Molecular Weight: 530.659
• Mol file: 1448328-56-0.mol

Synonyms:(R)-4-(benzyloxy)-1-((2R,5S)-5-((S)-hydroxy((2R,4S,5R)-5-(hydroxymethyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)butan-1-ol

Chemical Property of (R)-4-(benzyloxy)-1-((2R,5S)-5-((S)-hydroxy((2R,4S,5R)-5-(hydroxymethyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)butan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-(benzyloxy)-1-((2R,5S)-5-((S)-hydroxy((2R,4S,5R)-5-(hydroxymethyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)butan-1-ol

There total 11 articles about (R)-4-(benzyloxy)-1-((2R,5S)-5-((S)-hydroxy((2R,4S,5R)-5-(hydroxymethyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)butan-1-ol 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: 69.0%

(2R,3S,5Z,7S,10E)-14-(benzyloxy)-3-((4-methoxybenzyl)oxy)-5-methyltetradeca-5,10-diene-1,2,7-triol (1448328-55-9) → (R)-4-(benzyloxy)-1-((2R,5S)-5-((S)-hydroxy((2R,4S,5R)-5-(hydroxymethyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)butan-1-ol (1448328-56-0)

Guidance literature:

With pyridine N-oxide; potassium osmate(VI) dihydrate; zinc trifluoromethanesulfonate; citric acid; In aq. phosphate buffer; acetonitrile; at 60 - 80 ℃; for 36h; Reagent/catalyst; Solvent; Temperature;

DOI:10.1002/anie.201208919

Reference yield:

(2R,3S,7S,E)-14-(benzyloxy)-1,2-bis((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)tetradec-10-en-5-yn-7-ol (1448328-52-6) → (R)-4-(benzyloxy)-1-((2R,5S)-5-((S)-hydroxy((2R,4S,5R)-5-(hydroxymethyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)butan-1-ol (1448328-56-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: iron(III)-acetylacetonate; 1,2-bis-(diphenylphosphino)ethane / tetrahydrofuran / 0.17 h / -78 °C

1.2: 20 h / -78 - 0 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 - 20 °C

3.1: zinc trifluoromethanesulfonate; pyridine N-oxide; citric acid; potassium osmate(VI) dihydrate / acetonitrile; aq. phosphate buffer / 36 h / 60 - 80 °C

With pyridine N-oxide; potassium osmate(VI) dihydrate; iron(III)-acetylacetonate; tetrabutyl ammonium fluoride; zinc trifluoromethanesulfonate; 1,2-bis-(diphenylphosphino)ethane; citric acid; In tetrahydrofuran; aq. phosphate buffer; acetonitrile;

DOI:10.1002/anie.201208919

Reference yield:

(2R,3S,5Z,7S,10E)-14-(benzyloxy)-1,2-bis((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-5-methyltetradeca-5,10-dien-7-ol (1448328-54-8) → (R)-4-(benzyloxy)-1-((2R,5S)-5-((S)-hydroxy((2R,4S,5R)-5-(hydroxymethyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)butan-1-ol (1448328-56-0)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 0 - 20 °C

2: zinc trifluoromethanesulfonate; pyridine N-oxide; citric acid; potassium osmate(VI) dihydrate / acetonitrile; aq. phosphate buffer / 36 h / 60 - 80 °C

With pyridine N-oxide; potassium osmate(VI) dihydrate; tetrabutyl ammonium fluoride; zinc trifluoromethanesulfonate; citric acid; In tetrahydrofuran; aq. phosphate buffer; acetonitrile;

DOI:10.1002/anie.201208919

upstream raw materials:

(2R,3S,7S,E)-14-(benzyloxy)-1,2-bis((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)tetradec-10-en-5-yn-7-ol

(2R,3S,5Z,7S,10E)-14-(benzyloxy)-1,2-bis((tert-butyldimethylsilyl)oxy)-3-((4-methoxybenzyl)oxy)-5-methyltetradeca-5,10-dien-7-ol

(2R,3S,5Z,7S,10E)-14-(benzyloxy)-3-((4-methoxybenzyl)oxy)-5-methyltetradeca-5,10-diene-1,2,7-triol

(E)-di-tert-butyl-4-octene-1,8-dioate

Downstream raw materials:

(R)-4-(benzyloxy)-1-((2R,5S)-5-((S)-((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)(hydroxy)methyl)tetrahydrofuran-2-yl)butyl acetate

(R)-1-((2R,5S)-5-((S)-((tert-butyldimethylsilyl)oxy)((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)-4-hydroxybutyl acetate

(1R,4S,5R)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-((2R,5S)-5-((S)-((tert-butyldimethylsilyl)oxy)((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)-4-hydroxy-5-methyl-6-oxohexyl acetate

(1R,4S,5R)-6-((R)-4-benzyl-2-oxooxazolidin-3-yl)-1-((2R,5S)-5-((S)-((tert-butyldimethylsilyl)oxy)((2R,4S,5R)-5-(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-methoxybenzyl)oxy)-2-methyltetrahydrofuran-2-yl)methyl)tetrahydrofuran-2-yl)-5-methyl-6-oxo-4-((triethylsilyl)oxy)hexyl acetate