5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranose

Base Information

• Chemical Name: 5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranose
• CAS No.: 174590-90-0
• Molecular Formula: C₃₀H₃₆O₅Si
• Molecular Weight: 504.698

Synonyms:5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranose

Chemical Property of 5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranose

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranose

There total 10 articles about 5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranose 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%

5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone (130222-84-3) + phenyllithium (591-51-5) → 5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranose (174590-90-0)

Guidance literature:

In tetrahydrofuran; at -78 ℃;

DOI:10.1246/cl.1996.67

Reference yield: 71.5%

bromobenzene (108-86-1,52753-63-6) + 5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone (130222-84-3) → 5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranose (174590-90-0)

Guidance literature:

bromobenzene; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

Reference yield:

2,3-O-isopropylidene-D-ribofuranose (67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1) → 5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-D-ribofuranose (174590-90-0)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

2: 75.8 g / PCC; Celite 545 / CH₂Cl₂ / 16 h / 20 °C

3: 79 percent / cyclohexane; diethyl ether; tetrahydrofuran / 2 h / -78 °C

With dmap; Celite; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane;

DOI:10.1021/ja037211z

upstream raw materials:

5-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-D-ribono-1,4-lactone

phenyllithium

tert-butylchlorodiphenylsilane

(3aR,6R,6aR)-6-Hydroxymethyl-2,2-dimethyl-4-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ol

Downstream raw materials:

tert-butyl(((3aR,4R,6S,6aS)-2,2-dimethyl-6-phenyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methoxy)diphenylsilane

α-(1R,5R,8R)-3,3-dimethyl-6-phenyl-6-(2'-propenyl)-8-(tert-butyldiphenylsilyloxymethyl)-2,4,7-trioxabicyclo[3.3.0]octane

1-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-αD-ribofuranosyl]-N-benzoylcytosine

1-[5-O-(tert-butyldiphenylsilyl)-2,3-O-isopropylidene-1-phenyl-βD-ribofuranosyl]-N-benzoylcytosine

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