tert-butyl(((3aR,4R,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)diphenylsilane

Base Information

• Chemical Name: tert-butyl(((3aR,4R,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)diphenylsilane
• CAS No.: 805245-40-3
• Molecular Formula: C₄₄H₄₅IO₄Si
• Molecular Weight: 792.829
• Mol file: 805245-40-3.mol

Synonyms:tert-butyl(((3aR,4R,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)diphenylsilane

Chemical Property of tert-butyl(((3aR,4R,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)diphenylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl(((3aR,4R,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)diphenylsilane

There total 16 articles about tert-butyl(((3aR,4R,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)diphenylsilane 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%

tert-butylchlorodiphenylsilane (58479-61-1) + (3aS,4R,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol (805245-39-0) → tert-butyl(((3aR,4R,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)diphenylsilane (805245-40-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;

Reference yield:

(3aR,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one (805245-38-9) → tert-butyl(((3aR,4R,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)diphenylsilane (805245-40-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / NaBH₄; CeCl₃ / methanol / 0.5 h / 0 °C

2: 95 percent / imidazole / dimethylformamide / 40 °C

With 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.08.047 DOI:10.1081/NCN-200060286

Reference yield:

(3aR,6aR)-2,2-dimethyl-6-[(trityloxy)methyl]-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one (88559-56-2) → tert-butyl(((3aR,4R,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)diphenylsilane (805245-40-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / I₂; pyridine / CCl₄ / 12 h / 20 °C

2: 97 percent / NaBH₄; CeCl₃ / methanol / 0.5 h / 0 °C

3: 95 percent / imidazole / dimethylformamide / 40 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; iodine; In methanol; tetrachloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.08.047 DOI:10.1081/NCN-200060286

upstream raw materials:

tert-butylchlorodiphenylsilane

(3aS,4R,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

(3aR,6aR)-2,2-dimethyl-6-[(trityloxy)methyl]-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-4-one

(3aR,6aR)-5-iodo-2,2-dimethyl-6-((trityloxy)methyl)-3aH-cyclopenta[d][1,3]dioxol-4(6aH)-one

Downstream raw materials:

((3aS,4S,6aR)-4-(6-amino-9H-purin-9-yl)-5-fluoro-2,2-dimethyl-3a,6a-dihydro-4H-cyclopenta[d][1,3]dioxol-6-yl)methanol

(3aS,4R,6aR)-5-fluoro-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-ol

(3aR,4R,6aR)-5-fluoro-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl methanesulfonate

(1S,4R,5S)-1-(6-aminopurine-9-yl)-2-fluoro-4,5-(O-isopropylidenedioxy)-3-(trityloxymethyl)-2-cyclopentene