2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose

Base Information

• Chemical Name: 2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose
• CAS No.: 159299-30-6
• Molecular Formula: C₃₂H₄₂O₆Si
• Molecular Weight: 550.767
• Mol file: 159299-30-6.mol

Synonyms:2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose

Chemical Property of 2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose

There total 4 articles about 2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-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: 60.3%

tert-butyldimethylsilyl chloride (18162-48-6) + 1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose (159299-28-2) → 3-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose + 2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose (159299-30-6)

Guidance literature:

With silver nitrate; In tetrahydrofuran; pyridine; at 20 ℃; for 20h;

DOI:10.1002/1522-2675(20000809)83:8<1791::AID-HLCA1791>3.0.CO;2-K

Reference yield:

2,3,5-tri-O-benzyl-1-deoxy-D-ribofuranose (14233-62-6,81799-90-8) → 2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose (159299-30-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 95.3 percent / cyclohexene / 20 percent Pd(OH)2/C / ethanol / 4 h / Heating

2: 85.9 percent / Et₃N / pyridine / 20 °C

3: 60.3 percent / AgNO₃ / tetrahydrofuran; pyridine / 20 h / 20 °C

With silver nitrate; triethylamine; cyclohexene; palladium dihydroxide; In tetrahydrofuran; pyridine; ethanol; 1: Catalytic hydrogenation / 2: Etherification / 3: Etherification;

DOI:10.1002/1522-2675(20000809)83:8<1791::AID-HLCA1791>3.0.CO;2-K

Reference yield:

1,4-anhydro-D-ribitol (491-19-0,3169-91-3,3169-92-4,3999-31-3,39798-06-6,39999-42-3,41935-96-0,41936-38-3,51607-76-2,51607-78-4,53448-53-6,58716-62-4,106248-68-4,106707-70-4,120442-63-9) → 2-O-[(tert-butyl)dimethylsilyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose (159299-30-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 85.9 percent / Et₃N / pyridine / 20 °C

2: 60.3 percent / AgNO₃ / tetrahydrofuran; pyridine / 20 h / 20 °C

With silver nitrate; triethylamine; In tetrahydrofuran; pyridine; 1: Etherification / 2: Etherification;

DOI:10.1002/1522-2675(20000809)83:8<1791::AID-HLCA1791>3.0.CO;2-K

upstream raw materials:

tert-butyldimethylsilyl chloride

1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose

2,3,5-tri-O-benzyl-1-deoxy-D-ribofuranose

1,4-anhydro-D-ribitol

Downstream raw materials:

2-O-(tert-butyldimethylsilyl)-3-O-[(2-cyanoethoxy)(N,N-diisopropylamino)phosphanyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose