3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-4'-hydroxymethyl-1',2'-O-isopropylidene-α-D-ribofuranose

Base Information

• Chemical Name: 3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-4'-hydroxymethyl-1',2'-O-isopropylidene-α-D-ribofuranose
• CAS No.: 247025-11-2
• Molecular Formula: C₂₅H₃₃N₃O₅Si
• Molecular Weight: 483.64
• Mol file: 247025-11-2.mol

Synonyms:3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-4'-hydroxymethyl-1',2'-O-isopropylidene-α-D-ribofuranose

Chemical Property of 3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-4'-hydroxymethyl-1',2'-O-isopropylidene-α-D-ribofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-4'-hydroxymethyl-1',2'-O-isopropylidene-α-D-ribofuranose

There total 6 articles about 3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-4'-hydroxymethyl-1',2'-O-isopropylidene-α-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: 62.0%

tert-butylchlorodiphenylsilane (58479-61-1) + 3-Azido-3-deoxy-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose (247025-10-1) → 3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-4'-hydroxymethyl-1',2'-O-isopropylidene-α-D-ribofuranose (247025-11-2)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4039(99)01324-6

Reference yield:

3-Azido-5-O-benzoyl-4-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (153914-98-8) → 3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-4'-hydroxymethyl-1',2'-O-isopropylidene-α-D-ribofuranose (247025-11-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / K₂CO₃ / H₂O; methanol / 0 °C

2: 62 percent / Et₃N / CH₂Cl₂ / 20 °C

With potassium carbonate; triethylamine; In methanol; dichloromethane; water; 1: deprotection / 2: Etherification;

DOI:10.1016/S0040-4039(99)01324-6

Reference yield:

1-2 O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose (908142-25-6) → 3'-azido-5'-O-tert-butyldiphenylsilyl-3'-deoxy-4'-hydroxymethyl-1',2'-O-isopropylidene-α-D-ribofuranose (247025-11-2)

Guidance literature:

Multi-step reaction with 8 steps

1: sodium periodate / water; 1,4-dioxane / 0 - 20 °C

2: sodium hydroxide; water / tetrahydrofuran / 0 - 20 °C

3: pyridine / 0 - 20 °C / Inert atmosphere

4: hydrogen; palladium 10% on activated carbon; acetic acid / methanol / 72 h / 50 °C

5: pyridine / dichloromethane / 2 h / -20 °C / Inert atmosphere

6: tetra-(n-butyl)ammonium iodide; sodium azide / N,N-dimethyl-formamide / 100 °C / Inert atmosphere

7: water; potassium carbonate / methanol / 5 h / 0 °C

8: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere

With pyridine; sodium periodate; sodium azide; palladium 10% on activated carbon; water; hydrogen; tetra-(n-butyl)ammonium iodide; potassium carbonate; acetic acid; triethylamine; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

tert-butylchlorodiphenylsilane

3-Azido-3-deoxy-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

3-Azido-5-O-benzoyl-4-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

1-2,5-6 di-O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose

Downstream raw materials:

(2aS,2bR,5aR,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dimethyl-hexahydro-3,5,6-trioxa-2-aza-cyclobuta[a]pentalene

[(3aR,5R,6S,6aR)-6-Amino-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-methanol

1-[(2aS,2bR,5aR,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dimethyl-tetrahydro-3,5,6-trioxa-2-aza-cyclobuta[a]pentalen-2-yl]-2,2,2-trifluoro-ethanone

(2aS,2bR,5aR,6aS)-6a-(tert-Butyl-diphenyl-silanyloxymethyl)-4,4-dimethyl-tetrahydro-3,5,6-trioxa-2-aza-cyclobuta[a]pentalene-2-carboxylic acid benzyl ester