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

Base Information

• Chemical Name: (S)-1-((2R,3R,4R,5S)-4-Benzyloxy-3-hydroxy-5-phenyl-tetrahydro-furan-2-yl)-ethane-1,2-diol
• CAS No.: 481063-42-7
• Molecular Formula: C₁₉H₂₂O₅
• Molecular Weight: 330.381
• Mol file: 481063-42-7.mol

Synonyms:(S)-1-((2R,3R,4R,5S)-4-Benzyloxy-3-hydroxy-5-phenyl-tetrahydro-furan-2-yl)-ethane-1,2-diol

Chemical Property of (S)-1-((2R,3R,4R,5S)-4-Benzyloxy-3-hydroxy-5-phenyl-tetrahydro-furan-2-yl)-ethane-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-((2R,3R,4R,5S)-4-Benzyloxy-3-hydroxy-5-phenyl-tetrahydro-furan-2-yl)-ethane-1,2-diol

There total 10 articles about (S)-1-((2R,3R,4R,5S)-4-Benzyloxy-3-hydroxy-5-phenyl-tetrahydro-furan-2-yl)-ethane-1,2-diol 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: 63.0%

(R)-((2S,3R,4R,5S)-4-Benzyloxy-3-hydroxy-5-phenyl-tetrahydro-furan-2-yl)-hydroxy-acetaldehyde (481063-61-0) → (S)-1-((2R,3R,4R,5S)-4-Benzyloxy-3-hydroxy-5-phenyl-tetrahydro-furan-2-yl)-ethane-1,2-diol (481063-42-7)

Guidance literature:

With lithium aluminium tetrahydride; 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)-1-((2R,3R,4R,5S)-4-Benzyloxy-3-hydroxy-5-phenyl-tetrahydro-furan-2-yl)-ethane-1,2-diol (481063-42-7)

Guidance literature:

Multi-step reaction with 10 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

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

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)-1-((2R,3R,4R,5S)-4-Benzyloxy-3-hydroxy-5-phenyl-tetrahydro-furan-2-yl)-ethane-1,2-diol (481063-42-7)

Guidance literature:

Multi-step reaction with 8 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

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

DOI:10.1055/s-2002-33531

upstream raw materials:

(R)-((2S,3R,4R,5S)-4-Benzyloxy-3-hydroxy-5-phenyl-tetrahydro-furan-2-yl)-hydroxy-acetaldehyde

D-glucurono-6,3-lactone

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

D-glucurono-3,6-lactone acetonide

Downstream raw materials:

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

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

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