2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5-α-iodo-4,20-epoxy-D-seco-paclitaxel 1,2-carbonate

Base Information

• Chemical Name: 2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5-α-iodo-4,20-epoxy-D-seco-paclitaxel 1,2-carbonate
• CAS No.: 225660-83-3
• Molecular Formula: C₅₁H₇₀INO₁₂Si₂
• Molecular Weight: 1072.19
• Mol file: 225660-83-3.mol

Synonyms:2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5-α-iodo-4,20-epoxy-D-seco-paclitaxel 1,2-carbonate

Chemical Property of 2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5-α-iodo-4,20-epoxy-D-seco-paclitaxel 1,2-carbonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5-α-iodo-4,20-epoxy-D-seco-paclitaxel 1,2-carbonate

There total 4 articles about 2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5-α-iodo-4,20-epoxy-D-seco-paclitaxel 1,2-carbonate 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: 96.0%

2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5-α-iodo-20-hydroxy-D-seco-paclitaxel 1,2-carbonate (225660-82-2) → 2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5-α-iodo-4,20-epoxy-D-seco-paclitaxel 1,2-carbonate (225660-83-3)

Guidance literature:

With dmap; trifluoromethane sulfonyl chloride; In dichloromethane; for 0.833333h; Ambient temperature;

DOI:10.1021/jo982095h

Reference yield:

triethylsilyl chloride (994-30-9) → 2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5-α-iodo-4,20-epoxy-D-seco-paclitaxel 1,2-carbonate (225660-83-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) imidazole, 2.) imidazole / 1.) DMF, 60 deg C, 2 h, 2.) DMF, room temp., 1 h

2: 66 percent / Triton B / CH₂Cl₂; methanol / 2 h / -15 - -10 °C

3: 85 percent / CH₂Cl₂ / 24 h / 35 - 40 °C

4: 93 percent / Me₃SiI / CH₂Cl₂ / 0.75 h / -78 °C

5: 96 percent / DMAP, trifluoromethanesulfonyl chloride / CH₂Cl₂ / 0.83 h / Ambient temperature

With 1H-imidazole; dmap; trimethylsilyl iodide; trifluoromethane sulfonyl chloride; N-benzyl-trimethylammonium hydroxide; In methanol; dichloromethane;

DOI:10.1021/jo982095h

Reference yield:

2'-O-(tert-butyldimethylsilyl)-4-O-deacetyl-2-O-debenzoyl-7-O-(triethylsilyl)paclitaxel (160768-75-2) → 2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5-α-iodo-4,20-epoxy-D-seco-paclitaxel 1,2-carbonate (225660-83-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / CH₂Cl₂ / 24 h / 35 - 40 °C

2: 93 percent / Me₃SiI / CH₂Cl₂ / 0.75 h / -78 °C

3: 96 percent / DMAP, trifluoromethanesulfonyl chloride / CH₂Cl₂ / 0.83 h / Ambient temperature

With dmap; trimethylsilyl iodide; trifluoromethane sulfonyl chloride; In dichloromethane;

DOI:10.1021/jo982095h

upstream raw materials:

2'-(tert-butyldimethylsilyl)-2-debenzoyl-4-deacetyl-7-(triethylsilyl)-5-α-iodo-20-hydroxy-D-seco-paclitaxel 1,2-carbonate

triethylsilyl chloride

2'-(tert-butyldimethylsilyl)-7-(triethylsilyl)paclitaxel

2'-O-(tert-butyldimethylsilyl)-4-O-deacetyl-2-O-debenzoyl-7-O-(triethylsilyl)paclitaxel

Downstream raw materials:

C₅₁H₇₁I₂NO₁₂Si₂

2'-(tert-butyldimethylsilyl)-4-deacetyl-7-(triethylsilyl)-5,20-deoxy-5,20-selenapaclitaxel

C₅₁H₇₂INO₁₂Si₂

C₅₃H₇₃NO₁₃Si₂