(4S,5S)-4-(benzyloxy)-5-((1R,2R,3S)-3-(tert-butyldimethylsilyloxy)-1,2-dihydroxy-3-phenylpropyl)dihydrofuran-2(3H)-one

Base Information

• Chemical Name: (4S,5S)-4-(benzyloxy)-5-((1R,2R,3S)-3-(tert-butyldimethylsilyloxy)-1,2-dihydroxy-3-phenylpropyl)dihydrofuran-2(3H)-one
• CAS No.: 1311946-56-1
• Molecular Formula: C₂₆H₃₆O₆Si
• Molecular Weight: 472.654

Synonyms:(4S,5S)-4-(benzyloxy)-5-((1R,2R,3S)-3-(tert-butyldimethylsilyloxy)-1,2-dihydroxy-3-phenylpropyl)dihydrofuran-2(3H)-one

Chemical Property of (4S,5S)-4-(benzyloxy)-5-((1R,2R,3S)-3-(tert-butyldimethylsilyloxy)-1,2-dihydroxy-3-phenylpropyl)dihydrofuran-2(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (4S,5S)-4-(benzyloxy)-5-((1R,2R,3S)-3-(tert-butyldimethylsilyloxy)-1,2-dihydroxy-3-phenylpropyl)dihydrofuran-2(3H)-one

There total 9 articles about (4S,5S)-4-(benzyloxy)-5-((1R,2R,3S)-3-(tert-butyldimethylsilyloxy)-1,2-dihydroxy-3-phenylpropyl)dihydrofuran-2(3H)-one 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: 58.0%

(4S,5S)-4-(benzyloxy)-5-((R,E)-3-(tert-butyldimethyl-silyloxy)-3-phenylprop-1-enyl)dihydrofuran-2(3H)-one (1311946-55-0) → (4S,5S)-4-(benzyloxy)-5-((1R,2R,3S)-3-(tert-butyldimethylsilyloxy)-1,2-dihydroxy-3-phenylpropyl)dihydrofuran-2(3H)-one (1311946-56-1)

Guidance literature:

With osmium(VIII) oxide; methanesulfonamide; AD-mix β; In water; tert-butyl alcohol; at 0 ℃; for 24h;

DOI:10.1016/j.tet.2011.04.014

Reference yield:

1,4-anhydro-2-deoxy-5,6-O-isopropylidene-3-O-benzyl-L-arabino-hex-1-enitol (1169393-30-9) → (4S,5S)-4-(benzyloxy)-5-((1R,2R,3S)-3-(tert-butyldimethylsilyloxy)-1,2-dihydroxy-3-phenylpropyl)dihydrofuran-2(3H)-one (1311946-56-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: mercury(II) diacetate / tetrahydrofuran; water / 0.5 h / 25 °C

1.2: 0.25 h / 0 °C

1.3: 2.5 h / 0 °C

2.1: dipyridinium dichromate / dichloromethane / 2 h / Molecular sieve; Reflux

3.1: water; acetic acid / 20 °C

4.1: pyridine / 3 h / 0 °C

5.1: sodium iodide / butanone / 12 h / Reflux

6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 8 h / Inert atmosphere; Reflux

7.1: 1H-imidazole / dichloromethane / 8 h / 0 - 20 °C

8.1: osmium(VIII) oxide; AD-mix β; methanesulfonamide / water; tert-butyl alcohol / 24 h / 0 °C

With pyridine; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; osmium(VIII) oxide; dipyridinium dichromate; methanesulfonamide; AD-mix β; mercury(II) diacetate; water; acetic acid; sodium iodide; In tetrahydrofuran; dichloromethane; water; butanone; tert-butyl alcohol; 6.1: olefin cross metathesis reaction;

DOI:10.1016/j.tet.2011.04.014

Reference yield:

(4S,5S)-4-(benzyloxy)-5-((S)-1,2-dihydroxyethyl)dihydro-furan-2(3H)-one (1311946-39-0) → (4S,5S)-4-(benzyloxy)-5-((1R,2R,3S)-3-(tert-butyldimethylsilyloxy)-1,2-dihydroxy-3-phenylpropyl)dihydrofuran-2(3H)-one (1311946-56-1)

Guidance literature:

Multi-step reaction with 5 steps

1: pyridine / 3 h / 0 °C

2: sodium iodide / butanone / 12 h / Reflux

3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 8 h / Inert atmosphere; Reflux

4: 1H-imidazole / dichloromethane / 8 h / 0 - 20 °C

5: osmium(VIII) oxide; AD-mix β; methanesulfonamide / water; tert-butyl alcohol / 24 h / 0 °C

With pyridine; 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; osmium(VIII) oxide; methanesulfonamide; AD-mix β; sodium iodide; In dichloromethane; water; butanone; tert-butyl alcohol; 3: olefin cross metathesis reaction;

DOI:10.1016/j.tet.2011.04.014

upstream raw materials:

1,4-anhydro-2-deoxy-5,6-O-isopropylidene-3-O-benzyl-L-arabino-hex-1-enitol

(4S,5R)-4-(benzyloxy)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)dihydrofuran-2(3H)-one

(4S,5S)-4-(benzyloxy)-5-((S)-1,2-dihydroxyethyl)dihydro-furan-2(3H)-one

(4S,5S)-4-(benzyloxy)-5-vinyldihydrofuran-2(3H)-one

Downstream raw materials:

(4S,5S)-4-(benzyloxy)-5-((1R,2S,3S)-1,2,3-trihydroxy-3-phenylpropyl)dihydrofuran-2(3H)-one

(-)-cardiobutanolide

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