(3R,4S,5R)-5-(benzyloxymethyl)-3-fluoro-4-(triisopropylsilyloxy)dihydrofuran-2(3H)-one

Base Information

• Chemical Name: (3R,4S,5R)-5-(benzyloxymethyl)-3-fluoro-4-(triisopropylsilyloxy)dihydrofuran-2(3H)-one
• CAS No.: 1583260-31-4
• Molecular Formula: C₂₁H₃₃FO₄Si
• Molecular Weight: 396.575
• Mol file: 1583260-31-4.mol

Synonyms:(3R,4S,5R)-5-(benzyloxymethyl)-3-fluoro-4-(triisopropylsilyloxy)dihydrofuran-2(3H)-one

Chemical Property of (3R,4S,5R)-5-(benzyloxymethyl)-3-fluoro-4-(triisopropylsilyloxy)dihydrofuran-2(3H)-one

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5R)-5-(benzyloxymethyl)-3-fluoro-4-(triisopropylsilyloxy)dihydrofuran-2(3H)-one

There total 8 articles about (3R,4S,5R)-5-(benzyloxymethyl)-3-fluoro-4-(triisopropylsilyloxy)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: 90.0%

(4R,5R)-5-(benzyloxymethyl)-4-(triisopropylsilyloxy)dihydrofuran-2(3H)-one (1583260-30-3) → (3R,4S,5R)-5-(benzyloxymethyl)-3-fluoro-4-(triisopropylsilyloxy)dihydrofuran-2(3H)-one (1583260-31-4)

Guidance literature:

With manganese(II) bromide; N-fluorobis(benzenesulfon)imide; lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1.5h; diastereoselective reaction;

DOI:10.1021/ja502205q

Reference yield:

3-Benzyloxypropanal (19790-60-4) → (3R,4S,5R)-5-(benzyloxymethyl)-3-fluoro-4-(triisopropylsilyloxy)dihydrofuran-2(3H)-one (1583260-31-4)

Guidance literature:

Multi-step reaction with 5 steps

1: copper dichloride; (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid / ethyl acetate / 24 h / -30 °C / Molecular sieve

2: titanium(IV) dichlorodiisopropylate; boron trifluoride diethyl etherate / dichloromethane / 16 h / -40 °C / Inert atmosphere

3: zinc; water; trifluoroacetic acid / toluene / 32 h / 20 °C

4: 2,6-di-tert-butyl-pyridine / tetrahydrofuran / 5 h / 0 - 20 °C

5: N-fluorobis(benzenesulfon)imide; lithium hexamethyldisilazane; manganese(II) bromide / tetrahydrofuran / 1.5 h / -78 °C

With manganese(II) bromide; 2,6-di-tert-butyl-pyridine; titanium(IV) dichlorodiisopropylate; boron trifluoride diethyl etherate; (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid; water; N-fluorobis(benzenesulfon)imide; trifluoroacetic acid; copper dichloride; lithium hexamethyldisilazane; zinc; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; 2: |Mukaiyama Aldol Addition;

DOI:10.1021/ja502205q

Reference yield:

benzyl bromide (100-39-0) → (3R,4S,5R)-5-(benzyloxymethyl)-3-fluoro-4-(triisopropylsilyloxy)dihydrofuran-2(3H)-one (1583260-31-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.5 h / 0 °C

1.2: 16 h / 20 °C

2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 16 h / 20 °C

3.1: copper dichloride; (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid / ethyl acetate / 24 h / -30 °C / Molecular sieve

4.1: titanium(IV) dichlorodiisopropylate; boron trifluoride diethyl etherate / dichloromethane / 16 h / -40 °C / Inert atmosphere

5.1: zinc; water; trifluoroacetic acid / toluene / 32 h / 20 °C

6.1: 2,6-di-tert-butyl-pyridine / tetrahydrofuran / 5 h / 0 - 20 °C

7.1: N-fluorobis(benzenesulfon)imide; lithium hexamethyldisilazane; manganese(II) bromide / tetrahydrofuran / 1.5 h / -78 °C

With manganese(II) bromide; 2,6-di-tert-butyl-pyridine; titanium(IV) dichlorodiisopropylate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate; (R)-5-((1-Benzyl-1H-indol-3-yl)methyl)-2,2,3-trimethylimidazolin-4-one tetrafluoroboric acid; water; sodium hydride; N-fluorobis(benzenesulfon)imide; trifluoroacetic acid; copper dichloride; lithium hexamethyldisilazane; zinc; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; mineral oil; 4.1: |Mukaiyama Aldol Addition;

DOI:10.1021/ja502205q

upstream raw materials:

(3R,4R)-isopropyl 5-(benzyloxy)-3-hydroxy-4-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)pentanoate

5-benzyloxy-2-desoxy-3-hydroxy-D-lyxolactone

(R)-3-(benzyloxy)-2-(2,2,6,6-tetramethylpiperidin-1-yloxy)propanal

(4R,5R)-5-(benzyloxymethyl)-4-(triisopropylsilyloxy)dihydrofuran-2(3H)-one