5'-(tert-butyl-diphenyl-silanyloxymethyl)-2',3',4',5'-tetrahydro-2H-[2,2']bifuranyl-5-one

Base Information

• Chemical Name: 5'-(tert-butyl-diphenyl-silanyloxymethyl)-2',3',4',5'-tetrahydro-2H-[2,2']bifuranyl-5-one
• CAS No.: 203302-02-7
• Molecular Formula: C₂₅H₃₀O₄Si
• Molecular Weight: 422.596

Synonyms:5'-(tert-butyl-diphenyl-silanyloxymethyl)-2',3',4',5'-tetrahydro-2H-[2,2']bifuranyl-5-one

Chemical Property of 5'-(tert-butyl-diphenyl-silanyloxymethyl)-2',3',4',5'-tetrahydro-2H-[2,2']bifuranyl-5-one

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 5'-(tert-butyl-diphenyl-silanyloxymethyl)-2',3',4',5'-tetrahydro-2H-[2,2']bifuranyl-5-one

There total 3 articles about 5'-(tert-butyl-diphenyl-silanyloxymethyl)-2',3',4',5'-tetrahydro-2H-[2,2']bifuranyl-5-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: 34.0%

2-tert-butyldimethylsilyloxyfuran (121896-38-6) + (4R)-1-O-acetyl-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-L-ribofuranose (203301-81-9) → 5'-(tert-butyl-diphenyl-silanyloxymethyl)-2',3',4',5'-tetrahydro-2H-[2,2']bifuranyl-5-one (203302-02-7) + 5'-(tert-butyl-diphenyl-silanyloxymethyl)-2',3',4',5'-tetrahydro-2H-[2,2']bifuranyl-5-one (203523-09-5)

Guidance literature:

With t-butyldimethylsiyl triflate; In dichloromethane; at -90 ℃; for 1h;

DOI:10.1021/jo991568x

Reference yield:

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) → 5'-(tert-butyl-diphenyl-silanyloxymethyl)-2',3',4',5'-tetrahydro-2H-[2,2']bifuranyl-5-one (203302-02-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: imidazole / dimethylformamide

1.2: DIBAL-H / CH₂Cl₂ / -80 °C

1.3: 65 percent / DMAP; pyridine

2.1: 36 percent / tert-butyldimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 1 h / -90 °C

With 1H-imidazole; t-butyldimethylsiyl triflate; In dichloromethane; N,N-dimethyl-formamide; 1.1: silylation / 1.2: Reduction / 1.3: Acetylation / 2.1: Addition;

DOI:10.1021/jo991568x

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 5'-(tert-butyl-diphenyl-silanyloxymethyl)-2',3',4',5'-tetrahydro-2H-[2,2']bifuranyl-5-one (203302-02-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: imidazole / dimethylformamide

1.2: DIBAL-H / CH₂Cl₂ / -80 °C

1.3: 65 percent / DMAP; pyridine

2.1: 36 percent / tert-butyldimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 1 h / -90 °C

With 1H-imidazole; t-butyldimethylsiyl triflate; In dichloromethane; N,N-dimethyl-formamide; 1.1: silylation / 1.2: Reduction / 1.3: Acetylation / 2.1: Addition;

DOI:10.1021/jo991568x

upstream raw materials:

2-tert-butyldimethylsilyloxyfuran

(4R)-1-O-acetyl-5-O-tert-butyldiphenylsilyl-2,3-dideoxy-L-ribofuranose

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

tert-butylchlorodiphenylsilane

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