(S)-4-((2R,3R,4S,5S)-3,4-Bis-benzyloxy-5-phenyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolane

Base Information

• Chemical Name: (S)-4-((2R,3R,4S,5S)-3,4-Bis-benzyloxy-5-phenyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolane
• CAS No.: 481063-81-4
• Molecular Formula: C₂₉H₃₂O₅
• Molecular Weight: 460.57

Synonyms:(S)-4-((2R,3R,4S,5S)-3,4-Bis-benzyloxy-5-phenyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolane

Chemical Property of (S)-4-((2R,3R,4S,5S)-3,4-Bis-benzyloxy-5-phenyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolane

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of (S)-4-((2R,3R,4S,5S)-3,4-Bis-benzyloxy-5-phenyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolane

There total 12 articles about (S)-4-((2R,3R,4S,5S)-3,4-Bis-benzyloxy-5-phenyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolane 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: 95.0%

benzyl bromide (100-39-0) + (2S,3R,4R,5S)-4-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-phenyl-tetrahydro-furan-3-ol (481063-78-9) → (S)-4-((2R,3R,4S,5S)-3,4-Bis-benzyloxy-5-phenyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolane (481063-81-4)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran;

DOI:10.1055/s-2002-33531

Reference yield:

D-glucurono-6,3-lactone (63-29-6,487-44-5,575-64-4,14362-29-9,18281-92-0,26623-21-2) → (S)-4-((2R,3R,4S,5S)-3,4-Bis-benzyloxy-5-phenyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolane (481063-81-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 82 percent / H₂SO₄

2: 100 percent / imidazole / dimethylformamide

3: CeCl₃ / tetrahydrofuran / -78 - -60 °C

4: Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 0.08 h / -78 °C

5: 99 percent / Bu₄NF / tetrahydrofuran

6: DEAD; Ph₃P / tetrahydrofuran

7: K₂CO₃ / methanol

8: 95 percent / NaH; Bu₄NI / tetrahydrofuran

9: 93 percent / TFA / tetrahydrofuran

10: 63 percent / LiAlH₄ / tetrahydrofuran

11: 74 percent / PPTS / acetone

12: 95 percent / NaH; Bu₄NI / tetrahydrofuran

With 1H-imidazole; triethylsilane; lithium aluminium tetrahydride; cerium(III) chloride; sulfuric acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1055/s-2002-33531

Reference yield:

5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D glucofuraurono-6,3-lactone (126214-81-1) → (S)-4-((2R,3R,4S,5S)-3,4-Bis-benzyloxy-5-phenyl-tetrahydro-furan-2-yl)-2,2-dimethyl-[1,3]dioxolane (481063-81-4)

Guidance literature:

Multi-step reaction with 10 steps

1: CeCl₃ / tetrahydrofuran / -78 - -60 °C

2: Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 0.08 h / -78 °C

3: 99 percent / Bu₄NF / tetrahydrofuran

4: DEAD; Ph₃P / tetrahydrofuran

5: K₂CO₃ / methanol

6: 95 percent / NaH; Bu₄NI / tetrahydrofuran

7: 93 percent / TFA / tetrahydrofuran

8: 63 percent / LiAlH₄ / tetrahydrofuran

9: 74 percent / PPTS / acetone

10: 95 percent / NaH; Bu₄NI / tetrahydrofuran

With triethylsilane; lithium aluminium tetrahydride; cerium(III) chloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; acetone;

DOI:10.1055/s-2002-33531

upstream raw materials:

benzyl bromide

(2S,3R,4R,5S)-4-Benzyloxy-2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-phenyl-tetrahydro-furan-3-ol

D-glucurono-6,3-lactone

5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-α-D glucofuraurono-6,3-lactone

Downstream raw materials:

(S)-1-((2R,3R,4S,5S)-3,4-Bis-benzyloxy-5-phenyl-tetrahydro-furan-2-yl)-ethane-1,2-diol

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